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  • 1.
    Andaloussi, Mounir
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. ORGFARM.
    Sävmarker, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sjöberg, Per J.R.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates.2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 47, p. 13069-13074Article in journal (Refereed)
    Abstract [en]

    The first Pd-II-catalyzed P arylation has been performed by using palladium acetate, the rigid bidentate ligand dmphen (dmphen=2,9-dimethyl-1,10-phenanthroline), and without the addition of base or acid. Couplings of arylboronic acids or aryl trifluoroborates with H-phosphonate dialkyl esters were conducted in 30 min with controlled microwave (MW) heating under non-inert conditions. Aryl phosphites were also synthesized at room temperature with atmospheric air as the sole reoxidant. The arylated phosphonates were isolated in 44-90% yields. The excellent chemoselectivity of the method was illustrated in the synthesis of a Mycobacterium tuberculosis glutamine synthetase (MTB-GS) inhibitor. Online ESIMS was used to detect cationic palladium species in ongoing reactions directly, and a catalytic cycle has been proposed based on these results.

  • 2.
    Axelsson, Linda
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Veron, Jean-Baptiste
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sävmarker, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Odell, Luke
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    An Improved Palladium(II)-Catalyzed Method for the Synthesis of Aryl Ketones from Aryl Carboxylic Acids and Organonitriles2014In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 55, no 15, p. 2376-2380Article in journal (Refereed)
    Abstract [en]

    A palladium(II)-catalyzed decarboxylative protocol for the synthesis of aryl ketones has been developed. The addition of TFA was shown to improve the reaction yield and employing THF as solvent enabled the use of solid nitriles and in only a small excess. Using this method, five different benzoic acids reacted with a wide range of nitriles to produce 29 diverse (hetero)aryl ketone derivatives in up to 94% yield.

  • 3.
    Basu, Alex
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ålander, Eva
    Rise Bioeconomy.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    On the use of ion-crosslinked nanocellulose hydrogels for wound healing solutions: Physicochemical properties and application-oriented biocompatibility studies2017In: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 174, p. 299-308Article in journal (Refereed)
    Abstract [en]

    Calcium ion-crosslinked nanofibrillated cellulose (NFC) hydrogels were investigated as potential materials for wound healing dressings. The physicochemical properties of the hydrogels were examined by rheology and water retention tests. Skin cells and monocytes were selected for application-oriented bio-compatibility studies. The NFC hydrogels presented entangled fibrous networks and solid-like behavior. Water retention tests showed the material's potential to maintain a suitable moist environment for different type of wounds. The hydrogels did not affect dermal fibroblasts monolayer cultures upon directcontact, as cell monolayers remained intact after application, incubation and removal of the materials. Inflammatory response studies with blood-derived mononuclear cells revealed the inert nature of the hydrogels in terms of cytokine secretion and reactive oxygen species production. Results highlight the great potential of ion-crosslinked NFC hydrogels for the development of advanced wound dressings, where further functionalization of the material could lead to improved properties towards the healing of specific wound types.

  • 4.
    Carlsson, Daniel
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. Uppsala universitet.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Malaise, Jean-Luc
    GE Healthcare.
    On the pore space of agarose-based chromatography media2016Conference paper (Refereed)
  • 5.
    Carlsson, Daniel O.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Cooxidant-free TEMPO-mediated oxidation of highly crystalline nanocellulose in water2014In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, no 94, p. 52289-52298Article in journal (Refereed)
    Abstract [en]

    Selective oxidation of C6 hydroxyls to carboxyls through 2,2,6,6,-tetramethylpiperidine-1-oxyl (TEMPO)-mediated oxidation, where the oxidizing species (TEMPO+) is generated by cooxidants, such as NaBrO, NaClO or NaClO2, has become a popular way to modify the surfaces of nanocellulose fibrils in aqueous solutions. Employing highly crystalline nanocellulose from Cladophora sp. algae we demonstrate that the same degree of oxidation (D.O.) can be achieved within approximately the same time by replacing the cooxidants with electrogeneration of TEMPO+ in a bulk electrolysis setup. The D.O. is controlled by the oxidation time and the maximum D.O. achieved (D.O. 9.8%, 0.60 mmol g-1 of carboxylic acids and 0 mmol g-1 aldehydes) corresponds to complete oxidation of the surface-confined C6. This shows that TEMPO+ is not sterically hindered from completely oxidizing the fibril surface of Cladophora nanocellulose, in contrast to earlier hypotheses that were based on results with wood-derived nanocellulose. The oxidation does not significantly affect the morphology, the specific surface area (>115 m2 g-1) or the pore characteristics of the water-insoluble fibrous particles that were obtained after drying, but depolymerization corresponding to [similar]20% was observed. For extensive oxidation times, the product recovery of water-insoluble fibrils decreased significantly while significant amounts of charge passed through the system. This could indicate that the oxidation proceeds beyond the fibril surface, in contrast to the current view that TEMPO-mediated oxidation is confined only to the surface.

  • 6.
    Carlsson, Daniel O
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Cooxidant-free TEMPO-mediated oxidation of highly crystalline Cladophora nanocellulose2015Conference paper (Refereed)
  • 7.
    Carlsson, Daniel O
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Electrochemical TEMPO-mediated Oxidation of Highly Crystalline Nanocellulose in Water2014In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, p. 52289-52298Article in journal (Refereed)
  • 8.
    Carlsson, Daniel O
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Susceptibility of Iα- and Iβ-Dominated Cellulose to TEMPO-Mediated Oxidation2015In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 16, no 5, p. 1643-1649Article in journal (Refereed)
  • 9.
    Changqing, Ruan
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Maria, Strømme
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Jonas, Lindh
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    A green and simple method for preparation of an efficient palladium adsorbent based on 2,3-dialdehyde cellulose2015Conference paper (Refereed)
    Abstract [en]

    An efficient and green palladium adsorbent was prepared from 2,3-dialdehyde cellulose by reductive amination with a palladium chelating ligand in a facile one-pot procedure, and adsorption properties for palladium including adsorption isotherm, kinetics, desorption and recycling of the adsorbent obtained were studied. The successful reductive amination with the ligand and 2,3-dialdehyde cellulose was verified by FT-IR and XPS, and the adsorbent was characterized by SEM, XRD, gas adsorption and TGA. The adsorbent has a high adsorption capacity and enables fast adsorption of palladium from solution. Adsorbent materials suitable for both filters and column matrixes could be obtained.

  • 10.
    Changqing, Ruan
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    A green and simple method for preparation of an efficient palladium adsorbent based on cysteine functionalized2,3-dialdehyde cellulose2016In: Cellulose (London), ISSN 0969-0239, E-ISSN 1572-882X, Vol. 23, no 4, p. 2627-2638Article in journal (Refereed)
    Abstract [en]

    A green and efficient adsorbent for adsorption of palladium ions was prepared from 2,3-dialdehyde cellulose (DAC) originating from nanocellulose from the green algae Cladophora. The DAC was functionalized with cysteine via reductive amination in a convenient one-pot procedure to provide the adsorbent. The adsorption properties for adsorbing palladium(II) ions, including capacity, adsorption isotherm and kinetics, were studied. The successful reductive amination of cysteine with 2,3-dialdehyde cellulose was confirmed by FT-IR, elemental analysis and XPS. The adsorbent was characterized by SEM, XRD, gas adsorption and TGA. The adsorbent had a high adsorption capacity (130 mg palladium per gram adsorbent) and enabled fast adsorption of palladium(II) ions from solution (80 % of maximum capacity reached in 2 h). Adsorbent materials suitable for both filters (fibrous) and column matrixes (spherical particles) could be obtained in an efficient manner by controlling the degree of oxidation while producing the DAC material.

  • 11.
    Enquist, Per-Anders
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Nilsson, Peter
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Open-air oxidative Heck reactions at room temperature2006In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 8, no 4, p. 338-343Article in journal (Refereed)
    Abstract [en]

    Palladium(II)-catalyzed oxidative Heck arylation reactions proceed at room temperature with atmospheric air as the sole reoxidant. Using arylboronic acids as arylating agents and inexpensive 2,9-dimethyl-1,10-phenanthroline as the supporting ligand, efficient vinylic substitution reactions were obtained both with electron-poor and electron-rich olefins on a 1–50 mmol scale.

  • 12.
    Fardost, Ashkan
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sjöberg, Per J. R.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Analytical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Palladium(II)-Catalyzed Decarboxylative Heck Arylations of Acyclic Electron-Rich Olefins with Internal Selectivity2014In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 4, p. 870-878Article in journal (Refereed)
    Abstract [en]

    Despite the recent emergence of decarboxylative CC bond forming reactions, methodologies providing internally arylated electron-rich olefins are still lacking. We herein report on palladium(II)-catalyzed decarboxylative Heck arylations of linear electron-rich olefins with excellent selectivity for the internal position. The method allows a variety of electron-rich linear olefins to undergo arylation with ortho-functionalized aromatic carboxylic acids, including heterocycles. The reaction mechanism has been explored with ESI-MS studies to confirm previous findings, and to reveal the formation of a highly stable palladium complex as a result of the Heck product reacting with the catalyst.

  • 13.
    Ferraz, Natalia
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Basu, Alex
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Hong, Jaan
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Solid State Physics. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Immunology, Genetics and Pathology, Clinical Immunology.
    Celma, Gunta
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Heitz, Karen
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Welch, Ken
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    On the development of ion-crosslinked nanocellulose hydrogels for advanced wound care applications2019In: 6th International Polysaccharadide Conference EPNOE 2019, 2019Conference paper (Refereed)
  • 14.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Palladium(II)-Catalyzed Coupling Reactions2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Sustainable chemical processes are becoming increasingly important in all fields of synthetic chemistry. Catalysis can play an important role in developing environmentally benign chemical processes, and transition metals have an important role to play in the area of green chemistry. In particular, palladium(II) catalysis includes many key features for successful green chemistry methods, as demonstrated by a number of eco-friendly oxidation reactions catalyzed by palladium(II).

    The aim of the work presented in this thesis was to develop novel and greener palladium(II)-catalyzed coupling reactions. In striving to achieve this aim, the first open-vessel, room-temperature palladium(II)-catalyzed oxidative Heck reaction, using oxygen from the air as the reoxidant of palladium, was developed.

    In a further investigation of the palladium(II)-catalyzed oxidative Heck reaction, base-free conditions for the transformation were identified and suitable conditions for microwave-assisted oxidative Heck reactions were established.

    A convenient and low-cost palladium(II)-catalyzed method for the synthesis of styrene derivatives, by coupling arylboranes with vinyl acetate, was developed. The reaction mechanism was studied using ESI-MS, which enabled the detection of cationic palladium intermediates in ongoing productive reactions, and a plausible catalytic cycle was proposed.

    In an attempt to make the oxidative Heck and the styrene synthesis reactions more attractive from an industrial point of view, conditions for continuous flow synthesis were identified. The results were generally good and rapid synthesis of the desired products was obtained.

    The first palladium(II)-catalyzed C–P bond-forming Hirao-type reaction, employing arylboranes instead of the commonly used aryl halides, was developed. An ESI-MS study was performed, and a plausible catalytic pathway was suggested.

    Finally, a novel method for synthesizing aryl ketones from benzoic acids and nitriles, via palladium(II)-catalyzed decarboxylation of the benzoic acids, was established. Further, the reaction mechanism was studied by ESI-MS and a plausible catalytic route presented.

    List of papers
    1. Open-air oxidative Heck reactions at room temperature
    Open this publication in new window or tab >>Open-air oxidative Heck reactions at room temperature
    2006 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 8, no 4, p. 338-343Article in journal (Refereed) Published
    Abstract [en]

    Palladium(II)-catalyzed oxidative Heck arylation reactions proceed at room temperature with atmospheric air as the sole reoxidant. Using arylboronic acids as arylating agents and inexpensive 2,9-dimethyl-1,10-phenanthroline as the supporting ligand, efficient vinylic substitution reactions were obtained both with electron-poor and electron-rich olefins on a 1–50 mmol scale.

    National Category
    Medical and Health Sciences
    Identifiers
    urn:nbn:se:uu:diva-94792 (URN)10.1039/B517152K (DOI)
    Available from: 2006-09-14 Created: 2006-09-14 Last updated: 2017-12-14Bibliographically approved
    2. Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating
    Open this publication in new window or tab >>Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating
    Show others...
    2007 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 21, p. 7957-7962Article in journal (Refereed) Published
    Abstract [en]

    Scope and limitations of the base-free oxidative Heck reaction with arylboronic acids have been explored. Under our conditions, the dmphen−palladium(II)-catalyzed arylation proceeded with air or p-benzoquinone as reoxidants of palladium(0). We found that ambient temperature and mild aerobic conditions allow for the use of substrates sensitive to palladium(II)-catalyzed oxidation. Oxidative Heck couplings, employing different arylboronic acids, were smoothly and regioselectively conducted with both electron-rich and electron-poor olefins, providing high yields even with disubstituted butyl methacrylate, sensitive acrolein, and a vinylboronate ester. Controlled microwave processing was used to reduce reaction times from hours to minutes both in small scale and in 50 mmol scale batch processes.

    Keywords
    Acrylates/*chemistry, Aerobiosis, Benzene Derivatives/*chemistry, Boronic Acids/*chemistry, Catalysis, Chemistry; Organic/*methods, Heat, Microwaves, Oxidation-Reduction, Palladium/*chemistry, Temperature
    National Category
    Pharmaceutical Sciences
    Identifiers
    urn:nbn:se:uu:diva-16615 (URN)10.1021/jo701434s (DOI)000249986500019 ()17887706 (PubMedID)
    Available from: 2008-05-29 Created: 2008-05-29 Last updated: 2018-01-12Bibliographically approved
    3. Synthesis of styrenes by palladium(II)-catalyzed vinylation of arylboronic acids and aryltrifluoroborates by using vinyl acetate
    Open this publication in new window or tab >>Synthesis of styrenes by palladium(II)-catalyzed vinylation of arylboronic acids and aryltrifluoroborates by using vinyl acetate
    Show others...
    2009 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 18, p. 4630-4636Article in journal (Refereed) Published
    Abstract [en]

    Reactions of aromatic and heteroaromatic boronic acids or aryltrifluoroborate salts with vinyl acetate in the presence of a palladium(II) catalyst give the corresponding styrenes in good yields. This Heck reaction proceeds with microwave heating in less than 30 min at 140 degrees C in the absence of base and tolerates a variety of substituents. No palladium reoxidant is needed and the vinylation is performed under non-inert conditions. Mass spectrometry (electrospray ionization mass spectrometry (ESIMS) and tandem mass spectrometry   (MS/MS)) was used to identify cationic palladium-containing complexes in ongoing reactions. The key intermediates that have been detected, together with experiments that used deuterated vinyl acetate, support the existence of catalytically active palladium hydride species, and that it is the arylation of ethylene, not vinyl acetate, which   generates the styrene product. The mechanism of the reaction is discussed in terms of the palladium(II) intermediates mentioned above.

    Keywords
    Heck reaction, mass spectrometry, mechanistic studies, palladium, styrene
    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-102918 (URN)10.1002/chem.200802744 (DOI)000265955200018 ()19274694 (PubMedID)
    Available from: 2009-05-13 Created: 2009-05-12 Last updated: 2017-12-13Bibliographically approved
    4. Continuous Flow Palladium(II): Catalyzed Oxidative Heck Reactions with Arylboronic Acids
    Open this publication in new window or tab >>Continuous Flow Palladium(II): Catalyzed Oxidative Heck Reactions with Arylboronic Acids
    2010 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 12, p. 2270-2274Article in journal (Refereed) Published
    Abstract [en]

    Palladium(II)-catalyzed oxidative Heck reactions were investigated under continuous flow conditions. Selective, fast and convenient protocols for the coupling of arylboronic acids with electron-rich and electron-poor olefins were developed by using a commercially available flow reactor.

    Keywords
    Continuous flow, cross-coupling, Boron, Palladium, homogeneous catalysis, organic-synthesis, base-free, coupling reactions, room-temperature, bond formation, efficient, catalysis, palladium, air, perspective
    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-130028 (URN)10.1002/ejoc.201000063 (DOI)000277332500004 ()
    Available from: 2010-08-27 Created: 2010-08-27 Last updated: 2017-12-12Bibliographically approved
    5. Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates.
    Open this publication in new window or tab >>Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates.
    Show others...
    2009 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 47, p. 13069-13074Article in journal (Refereed) Published
    Abstract [en]

    The first Pd-II-catalyzed P arylation has been performed by using palladium acetate, the rigid bidentate ligand dmphen (dmphen=2,9-dimethyl-1,10-phenanthroline), and without the addition of base or acid. Couplings of arylboronic acids or aryl trifluoroborates with H-phosphonate dialkyl esters were conducted in 30 min with controlled microwave (MW) heating under non-inert conditions. Aryl phosphites were also synthesized at room temperature with atmospheric air as the sole reoxidant. The arylated phosphonates were isolated in 44-90% yields. The excellent chemoselectivity of the method was illustrated in the synthesis of a Mycobacterium tuberculosis glutamine synthetase (MTB-GS) inhibitor. Online ESIMS was used to detect cationic palladium species in ongoing reactions directly, and a catalytic cycle has been proposed based on these results.

    Place, publisher, year, edition, pages
    Weinheim: Wiley-VCH Verlag GmbH, 2009
    Keywords
    Boronic acids, microwave chemistry, palladium, P arylation, trifluoroborates
    National Category
    Analytical Chemistry
    Research subject
    Analytical Chemistry
    Identifiers
    urn:nbn:se:uu:diva-113919 (URN)10.1002/chem.200901473 (DOI)000273697100021 ()19856344 (PubMedID)
    Available from: 2010-02-04 Created: 2010-02-04 Last updated: 2017-12-12Bibliographically approved
    6.
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  • 15.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Carlsson, Daniel O
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Convenient One-Pot Formation of 2,3-Dialdehyde Cellulose Beads via Periodate Oxidation of Cellulose in Water2014In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 15, no 5, p. 1928-1932Article in journal (Refereed)
  • 16.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Carlsson, Daniel O
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    One-pot formation of 2,3-dialdehyde cellulose (DAC) beads2015Conference paper (Refereed)
  • 17.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. Uppsala universitet.
    Carlsson, Daniel
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Vall, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Spontaneous formation of 2,3-dialdehyde cellulose (DAC) beads via periodate oxidation and application of the beads as matrix material in protein purification2016Conference paper (Refereed)
  • 18.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Enquist, Per-Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Pilotti, Åke
    Nilsson, Peter
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating2007In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 21, p. 7957-7962Article in journal (Refereed)
    Abstract [en]

    Scope and limitations of the base-free oxidative Heck reaction with arylboronic acids have been explored. Under our conditions, the dmphen−palladium(II)-catalyzed arylation proceeded with air or p-benzoquinone as reoxidants of palladium(0). We found that ambient temperature and mild aerobic conditions allow for the use of substrates sensitive to palladium(II)-catalyzed oxidation. Oxidative Heck couplings, employing different arylboronic acids, were smoothly and regioselectively conducted with both electron-rich and electron-poor olefins, providing high yields even with disubstituted butyl methacrylate, sensitive acrolein, and a vinylboronate ester. Controlled microwave processing was used to reduce reaction times from hours to minutes both in small scale and in 50 mmol scale batch processes.

  • 19.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Fardost, Ashkan
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Almeida, Maria
    Nilsson, Peter
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Convenient Stille carbonylative cross-couplings using molybdenum hexacarbonyl2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 18, p. 2470-2472Article in journal (Refereed)
    Abstract [en]

    Palladium catalysis was used in Stille-type carbonylative cross-couplings employing Mo(CO)(6) as the carbon monoxide source. Robust and convenient transformations were carried out in closed vessels at 100 degrees C, providing a set of diaryl ketones in good yields. Aryl triflates and bromides were used as coupling partners with aryl stannanes. Inclusion of the Mo(CO)(6) destabilizing agent DBU made this protocol operationally simple and suppressed side-product formation. (C) 2010 Elsevier Ltd. All rights reserved.

  • 20.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Hua, Kai
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ruan, Changqing
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Rocha, Igor
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Carlsson, Daniel Otto
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Chemical Modifications of Nanocellulose2014In: NFM conference, Prague 16-18th June 2014., 2014Conference paper (Refereed)
  • 21.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. ORGFARM.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Microwave-assisted palladium(II)-catalyzed Heck reactions2009In: Chimica oggi, ISSN 0392-839X, E-ISSN 1973-8250, Vol. 27, no 2, p. 11-14Article in journal (Refereed)
    Abstract [en]

    During the last couple of years we have reported on a number of microwave promoted oxidative Heck reactions with the aim of developing efficient and environmentally benign procedures. The use of microwave irradiation has enabled us to drastically improve reaction rates and to use substrates which are virtually unreactive at lower temperatures. A few multi-gram scale batch reactions have also been successfully executed. Several different oxidants for regeneration of palladium(II) have been evaluated from which air is the most attractive due to its low-cost, ease-of-use and low environmental impact. The use of air as palladium reoxidant was made possible by employing bidentate nitrogen ligands.

  • 22.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ruan, Changqing
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Maria, Strømme
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Preparation of Porous Cellulose Beads via Introduction of Diamine Spacers2016In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 32, no 22, p. 5600-5607Article in journal (Refereed)
    Abstract [en]

    The current work presents a synthesis route based on the reductive amination of 2,3-dialdehyde cellulose beads with diamines to render micrometer-sized beads with increased specific surface area (SSA) and porosity in the mesoporous range. Specifically, the influence of the reductive amination of 2,3-dialdehyde cellulose (DAC) using aliphatic and aromatic tethered mono- and diamines on bead microstructure was investigated. Aliphatic and aromatic tethered monoamines were found to have limited utility for producing porous beads whereas the introduction of diamines provided beads with a porous texture and an SSA increasing from <1 to >30 m(2)/g. Both aliphatic and aromatic diamines were found to be useful in producing porous beads having a pore size distribution range of 10 to 100 nm, as verified by N-2 gas adsorption and mercury intrusion porosimetry analyses. The true density of the functionalized DAC beads decreased to an average of about 1.36 g/cm(3) as compared to 1.48 g/cm(3) for the unfunctionalized, fully oxidized DAC beads. The total porosity of the beads was, according to mercury porosimetry, in the range of 54-64%. Reductive amination with 1,7-diaminoheptane provided beads that were stable under alkaline conditions (I M NaOH). It was concluded that the introduction of tethered diamines into DAC beads is a facile method for producing mesoporous beads.

  • 23.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. ORGFARM.
    Sjöberg, Per J. R.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis of aryl ketones by palladium(II)-catalyzed decarboxylative addition of benzoic acids to nitriles2010In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, no 42, p. 7733-7737Article in journal (Refereed)
  • 24.
    Lindh, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. ORGFARM.
    Sävmarker, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Nilsson, Peter
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. ORGFARM.
    Sjöberg, Per J R
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis of styrenes by palladium(II)-catalyzed vinylation of arylboronic acids and aryltrifluoroborates by using vinyl acetate2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 18, p. 4630-4636Article in journal (Refereed)
    Abstract [en]

    Reactions of aromatic and heteroaromatic boronic acids or aryltrifluoroborate salts with vinyl acetate in the presence of a palladium(II) catalyst give the corresponding styrenes in good yields. This Heck reaction proceeds with microwave heating in less than 30 min at 140 degrees C in the absence of base and tolerates a variety of substituents. No palladium reoxidant is needed and the vinylation is performed under non-inert conditions. Mass spectrometry (electrospray ionization mass spectrometry (ESIMS) and tandem mass spectrometry   (MS/MS)) was used to identify cationic palladium-containing complexes in ongoing reactions. The key intermediates that have been detected, together with experiments that used deuterated vinyl acetate, support the existence of catalytically active palladium hydride species, and that it is the arylation of ethylene, not vinyl acetate, which   generates the styrene product. The mechanism of the reaction is discussed in terms of the palladium(II) intermediates mentioned above.

  • 25. Odell, L.
    et al.
    Sävmarker, J.
    Nilsson, Petter
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Larhed, Mats
    Addition Reactions with Formation of Carbon-Carbon Bonds: (v) The Oxidative Heck Reaction.2014In: Current Organic Synthesis II, Vol. 7, p. 492-534Article, review/survey (Refereed)
  • 26.
    Odell, Luke R.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. ORGFARM.
    Gustafsson, Tomas
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Continuous Flow Palladium(II): Catalyzed Oxidative Heck Reactions with Arylboronic Acids2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 12, p. 2270-2274Article in journal (Refereed)
    Abstract [en]

    Palladium(II)-catalyzed oxidative Heck reactions were investigated under continuous flow conditions. Selective, fast and convenient protocols for the coupling of arylboronic acids with electron-rich and electron-poor olefins were developed by using a commercially available flow reactor.

  • 27.
    Pan, Ruijun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Cheung, Ocean
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Wang, Zhaohui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Tammela, Petter
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Huo, Jinxing
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Applied Mechanics.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Edström, Kristina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Mesoporous Cladophora cellulose separators for lithium-ion batteries2016In: Journal of Power Sources, ISSN 0378-7753, E-ISSN 1873-2755, Vol. 321, p. 185-192Article in journal (Refereed)
    Abstract [en]

    Much effort is currently made to develop inexpensive and renewable materials which can replace the polyolefin microporous separators conventionally used in contemporary lithium-ion batteries. In the present work, it is demonstrated that mesoporous Cladophora cellulose (CC) separators constitute very promising alternatives based on their high crystallinity, good thermal stability and straightforward manufacturing. The CC separators, which are fabricated using an undemanding paper-making like process involving vacuum filtration, have a typical thickness of about 35 mu m, an average pore size of about 20 nm, a Young's modulus of 5.9 GPa and also exhibit an ionic conductivity of 0.4 mS cm(-1) after soaking with 1 M LiPF6 EC: DEC (1/1, v/v) electrolyte. The CC separators are demonstrated to be thermally stable at 150 degrees C and electrochemically inert in the potential range between 0 and 5 V vs. Li+/Li. A LiFePO4/Li cell containing a CC separator showed good cycling stability with 99.5% discharge capacity retention after 50 cycles at a rate of 0.2 C. These results indicate that the renewable CC separators are well-suited for use in high-performance lithium-ion batteries.

  • 28.
    Pan, Ruijun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Sun, Rui
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Wang, Zhaohui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Edström, Kristina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Double-sided conductive separators for lithium-metal batteries2019In: Energy Storage Materials, ISSN 2405-8297, Vol. 21, p. 464-473Article in journal (Refereed)
    Abstract [en]

    A novel double-sided conductive (DSC) separator consisting of two 5 μm-thick carbon nanotube (CNT)/cellulose nanofiber (CNF) composite layers coated on each side of a 20 μm-thick glass-fiber (GF)/CNF composite membrane is described. In a lithium-metal battery (LMB), the DSC separator exhibits a high ionic conductivity (i.e. 1.7 mS cm−1 using an LP40 electrolyte) due to the high porosity (i.e. 66%) of the GF/CNF membrane. More stable Li anodes can also be realized by depositing Li within the porous electronically conducting CNT/CNF matrix at the DSC separator anode side due to the decreased current density. The CNT/CNF layer of the DSC separator facing the cathode, which is in direct electric contact with the current collector, decreases the overpotential for the cathode and consequently improves its capacity and rate performance significantly. A Li/Li cell containing a DSC separator showed an improved cycling stability compared to an analogous cell equipped with a commercial Celgard separator at current densities up to 5 mA cm−2 for Li deposition and stripping capacities up to 5 mAh cm−2. A proof-of-concept LMB containing a lithium iron phosphate (LFP) composite cathode and a DSC separator showed a significantly improved rate capability, yielding capacities of about 110 mAh g−1 at 5 C and 80 mAh g−1 at 10 C. The LMB cell containing a DSC separator also exhibited a capacity retention of 80% after 200 cycles at a rate of 6 C indicating that the two-sided conductive separator design has significant potential in facilitating the development of well-functioning LMBs.

  • 29.
    Pan, Ruijun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Sun, Rui
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Wang, Zhaohui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Edström, Kristina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Sandwich-structured nano/micro fiber-based separators for lithium metal batteries2019In: Nano Energy, ISSN 2211-2855, E-ISSN 2211-3282, Vol. 55, p. 316-326Article in journal (Refereed)
    Abstract [en]

    Although the increased need for high-energy/power-density energy storage systems has revived the research on lithium metal batteries (LMBs), the influence of the separator on the performance of LMBs is still generally neglected. In the present study, a sandwich-structured separator (referred to as the CGC separator below) composed of two 2.5µm thick cellulose nanofiber (CNF) surface layers and an intermediate 15µm thick glass microfiber (GMF) and CNF composite layer is described. While the CNF surface layers of the CGC separator feature a homogeneous distribution of nano-sized pores favoring the attainment of a homogeneous current distribution at both electrodes, the intermediate GMF/CNF layer contains macropores facilitating the ionic transport through the separator. The CGC separator exhibited a much better electrolyte wettability and thermal stability compared to a Celgard separator, due to the use of the hydrophilic and thermally stable CNFs and GMFs. It is also shown that the combination of nano-sized and micro-sized fibers used in the CGC separator yields a higher ionic conductivity than that for the commercial separator (1.14 vs. 0.49 mS cm−1). Moreover, the influence of the separator pore structure (e.g. the porosity and pore distribution) on the performance of LMBs is studied for both Li anodes and LiFePO4 composite cathodes. The results demonstrate that the use of separators with high porosities and homogeneous surface pore distributions can improve the performances (e.g. capacities and stabilities) of LMBs considerably, and also highlights the importance of proper separator/electrode interactions. The present approach constitutes a practical engineering strategy for the production of separators with nano/micro fibers and a promising route for the development of LMBs with improved safety and enhanced electrochemical performances.

  • 30.
    Pan, Ruijun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry. Uppsala University.
    Wang, Zhaohui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Sun, Rui
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Edström, Kristina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Solid State Physics.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Solid State Physics. Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Polydopamine-based redox-active separator for lithium-ion batteriesIn: Article in journal (Refereed)
    Abstract [en]

    The performance of lithium-ion batteries (LIBs) can be effectively increased with functionalized separators. Herein, it is demonstrated that polydopamine-based redox-active (PRA) separators can provide additional capacity to that of typical anode materials, increase the volumetric capacity of the cell, as well as, decrease the cell resistance to yield an improved performance at higher cycling rates. The PRA separators, which are composed of a 2 µm thick electrically insulating nanocellulose fiber (NCF) layer and an 18 µm thick polydopamine (PDA) and carbon nanotube (CNT) containing redox-active layer, are readily produced using a facile paper-making process. The PRA separators are also easily wettable by commonly employed electrolytes (e.g. LP40) and exhibit a high dimensional stability even at elevated temperatures (e.g. 150 ºC). In addition, the pore structure endows the PRA separator with a high ionic conductivity (i.e. 1.06 mS cm-1 after soaking with LP40 electrolyte) that increases the rate performance of the cells. Due to the presence of the redox-active layer, Li4Ti5O12 (LTO) half-cells containing PRA separator were found to exhibit significantly higher capacities than the corresponding cells containing commercial separators. These results clearly show that the implementation of this type of redox-active separators constitutes a straightforward and effective way to increase the energy and power densities of LIBs.

  • 31.
    Pan, Ruijun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Wang, Zhaohui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Sun, Rui
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Edström, Kristina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Polydopamine-based redox-active separators for lithium-ion batteries2019In: Journal of Materiomics, ISSN 2352-8478, p. 204-213Article in journal (Refereed)
    Abstract [en]

    The performance of lithium-ion batteries (LIBs) can be effectively increased with functionalized separators. Herein, it is demonstrated that polydopamine-based redox-active (PRA) separators can provide additional capacity to that of typical anode materials, increase the volumetric capacity of the cell, as well as, decrease the cell resistance to yield an improved performance at higher cycling rates. The PRA separators, which are composed of a 2 μm thick electrically insulating nanocellulose fiber (NCF) layer and an 18 μm thick polydopamine (PDA) and carbon nanotube (CNT) containing redox-active layer, are readily produced using a facile paper-making process. The PRA separators are also easily wettable by commonly employed electrolytes (e.g. LP40) and exhibit a high dimensional stability. In addition, the pore structure endows the PRA separator with a high ionic conductivity (i.e. 1.06 mS cm−1) that increases the rate performance of the cells. Due to the presence of the redox-active layer, Li4Ti5O12 (LTO) half-cells containing PRA separator were found to exhibit significantly higher capacities than the corresponding cells containing commercial separators. These results clearly show that the implementation of this type of redox-active separators constitutes a straightforward and effective way to increase the energy and power densities of LIBs.

  • 32.
    Pan, Ruijun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Wang, Zhaohui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Sun, Rui
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Edström, Kristina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Thickness difference induced pore structure variations in cellulosic separators for lithium-ion batteries2017In: Cellulose (London), ISSN 0969-0239, E-ISSN 1572-882X, Vol. 24, no 7, p. 2903-2911Article in journal (Refereed)
    Abstract [en]

    The pore structure of the separator is crucial to the performance of a lithium-battery as it affects the cell resistance. Herein, a straightforward approach to vary the pore structure of Cladophora cellulose (CC) separators is presented. It is demonstrated that the pore size and porosity of the CC separator can be increased merely by decreasing the thickness of the CC separator by using less CC in the manufacturing of the separator. As the pore size and porosity of the CC separator are increased, the mass transport through the separator is increased which decreases the electrolyte resistance in the pores of the separator. This enhances the battery performance, particularly at higher cycling rates, as is demonstrated for LiFePO4/Li half-cells. A specific capacity of around 100 mAh g-1 was hence obtained at a cycling rate of 2 C with a 10 μm thick CC separator while specific capacities of 40 and close to 0 mAh g-1 were obtained for separators with thicknesses of 20 and 40 μm, respectively. As the results also showed that a higher ionic conductivity was obtained for the 10 μm thick CC separator than for the 20 and 40 μm thick CC separators, it is clear that the different pore structure of the separators was an important factor affecting the battery performance in addition to the separator thickness. The present straightforward, yet efficient, strategy for altering the pore structure hence holds significant promise for the manufacturing of separators with improved performance, as well as for fundamental studies of the influence of the properties of the separator on the performance of lithium-ion cells.

  • 33.
    Pan, Ruijun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Xu, Xingxing
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Solid State Electronics.
    Sun, Rui
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Wang, Zhaohui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Edström, Kristina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Nanocellulose Modified Polyethylene Separators for Lithium Metal Batteries2018In: Small, ISSN 1613-6810, E-ISSN 1613-6829, Vol. 14, no 21, article id 1704371Article in journal (Refereed)
    Abstract [en]

    Abstract Poor cycling stability and safety concerns regarding lithium (Li) metal anodes are two major issues preventing the commercialization of high‐energy density Li metal‐based batteries. Herein, a novel tri‐layer separator design that significantly enhances the cycling stability and safety of Li metal‐based batteries is presented. A thin, thermally stable, flexible, and hydrophilic cellulose nanofiber layer, produced using a straightforward paper‐making process, is directly laminated on each side of a plasma‐treated polyethylene (PE) separator. The 2.5 µm thick, mesoporous (≈20 nm average pore size) cellulose nanofiber layer stabilizes the Li metal anodes by generating a uniform Li+ flux toward the electrode through its homogenous nanochannels, leading to improved cycling stability. As the tri‐layer separator maintains its dimensional stability even at 200 °C when the internal PE layer is melted and blocks the ion transport through the separator, the separator also provides an effective thermal shutdown function. The present nanocellulose‐based tri‐layer separator design thus significantly facilitates the realization of high‐energy density Li metal‐based batteries.

  • 34.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Chemical modification of Cladophora nanocellulose to provide a non-toxic material with anticoagulant properties2015Conference paper (Refereed)
    Abstract [en]

    Blood purification is a common procedure for treating patients with kidney failure in which an extracorporeal device filled with a porous material containing antibodies can retain toxins from the blood. In order to avoid activation and coagulation, heparin is administrated to patients; however this sulfonated polysaccharide may cause many side effects such as intense bleeding and osteoporosis. In this project nanocellulose from Cladophora green algae was used for the development of a porous material with anticoagulant properties. A periodate oxidation followed by an amine cross-linking and subsequent reduction produced dialdehyde cellulose beads ranging from 10-100 mm in diameter with improved mechanical properties and high stability in alkaline media. This material was then sulfonated to acquire anticoagulant properties and characterized by FTIR, z-potential, condutometric titration, elemental analysis and BET surface area showing that its porosity varies with the degree of sulfonation. After extensive washing, toxicology experiments were performed with a THP-1 monocyte cell line in order to examine if the material was non-toxic and could be suitable as a matrix in blood purification.

  • 35.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Chemical modifications of Cladophorananocellulose to provide a non-toxicmaterial with anticoagulant properties2016Conference paper (Refereed)
  • 36.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Hemocompatibility of porous sulfonated Cladophora cellulose beads towards a blood purification material with anticoagulant properties2018In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 255Article in journal (Other academic)
  • 37.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Sulfonated cladophora cellulose beads as a material for biomedical applications 2015In: Fourth International Conference on Multifunctional, Hybrid and Nanomaterials: Hybrid Materials 2015, Sitges, 2015, p. P2.039-Conference paper (Refereed)
  • 38.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Sulfonated cladophora cellulose beads as a material for biomedical applications 2015In: Fourth International Conference on Multifunctional, Hybrid and Nanomaterials: Hybrid Materials 2015, Stiges, 2015, p. P2.039-Conference paper (Refereed)
  • 39.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Sulfonated Cladophora nanocellulose beads as a material for plasmapheresis2015Conference paper (Refereed)
  • 40.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Sulfonated Nanocellulose Beads as Potential Immunosorbents2018In: Cellulose (London), ISSN 0969-0239, E-ISSN 1572-882X, Vol. 28, no 3, p. 1899-1910Article in journal (Refereed)
    Abstract [en]

    Herein 2,3-dialdehyde cellulose beads prepared from Cladophora green algae nanocellulose were sulfonated and characterized by FTIR, conductometric titration, elemental analysis, SEM, ζ-potential, nitrogen adsorption–desorption and laser diffraction, aiming for its application as a potential immunosorbent material. Porous beads were prepared at mild reaction conditions in water and were chemically modified by sulfonation and reduction. The obtained 15 µm sized sulfonated beads were found to be highly charged and to have a high surface area of ~ 100 m2 g−1 and pore sizes between 20 and 60 nm, adequate for usage as immunosorbents. After reduction of remaining aldehyde groups, the beads could be classified as non-cytotoxic in indirect toxicity studies with human dermal fibroblasts as a first screening of their biocompatibility. The observed properties make the sulfonated cellulose beads interesting for further development as matrix material in immunosorbent devices.

  • 41.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Sulfonated nanocellulose beads from Cladophora green algae as a material for blood plasmapheresis2015Conference paper (Refereed)
  • 42.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Tailoring the structure of Cladophora nanocellulose towards a dialysis porous material with anti-coagulant properties2016Conference paper (Refereed)
  • 43.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. CAPES Foundation, Ministry of Education of Brazil, Brasília DF 70040-020, Brazil.
    Hattori, Yocefu
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Mirna, Diniz
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Spectroscopic and physicochemical characterization of sulfonated Cladophora cellulose beads2018In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 34, no 37, p. 11121-11125Article in journal (Refereed)
    Abstract [en]

    The work presents a full physicochemical characterization of sulfonated cellulose beads prepared from Cladophora nanocellulose intended for use in biological systems. 2,3-Dialdehyde cellulose (DAC) beads were sulfonated, and transformation of up to 50% of the aldehyde groups was achieved, resulting in highly charged and porous materials compared to the compact surface of the DAC beads. The porosity could be tailored by adjusting the degree of sulfonation, and a subsequent reduction of the aldehyde groups to hydroxyl groups maintained the bead structure without considerable alteration of the surface properties. The thermal stability of the DAC beads was significantly increased with the sulfonation and reduction reactions. Raman spectroscopy also showed to be a useful technique for the characterization of sulfonated cellulose materials.

  • 44.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. CAPES Foundation, Ministry of Education of Brazil, Brasília, DF 70040-020, Brazil.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Hong, Jaan
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Immunology, Genetics and Pathology, Clinical Immunology.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Ferraz, Natalia
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Blood Compatibility of Sulfonated Cladophora Nanocellulose Beads2018In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 23, no 3, article id 601Article in journal (Refereed)
    Abstract [en]

    Sulfonated cellulose beads were prepared by oxidation of Cladophora nanocellulose to 2,3-dialdehyde cellulose followed by sulfonation using bisulfite. The physicochemical properties of the sulfonated beads, i.e., high surface area, high degree of oxidation, spherical shape, and the possibility of tailoring the porosity, make them interesting candidates for the development of immunosorbent platforms, including their application in extracorporeal blood treatments. A desired property for materials used in such applications is blood compatibility; therefore in the present work, we investigate the hemocompatibility of the sulfonated cellulose beads using an in vitro whole blood model. Complement system activation (C3a and sC5b-9 levels), coagulation activation (thrombin-antithrombin (TAT) levels) and hemolysis were evaluated after whole blood contact with the sulfonated beads and the results were compared with the values obtained with the unmodified Cladophora nanocellulose. Results showed that neither of the cellulosic materials presented hemolytic activity. A marked decrease in TAT levels was observed after blood contact with the sulfonated beads, compared with Cladophora nanocellulose. However, the chemical modification did not promote an improvement in Cladophora nanocellulose hemocompatibility in terms of complement system activation. Even though the sulfonated beads presented a significant reduction in pro-coagulant activity compared with the unmodified material, further modification strategies need to be investigated to control the complement activation by the cellulosic materials.

  • 45.
    Rocha, Igor
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Cladophora nanocellulose as a material for biomedical applications2015In: Uppsala Biomaterials Conference 2015: A joint conference between local groups at Uppsala University working with biomaterials and their applications, 2015Conference paper (Refereed)
  • 46.
    Ruan, Changqing
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Gustafsson, Simon
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Cellulose nanofibers prepared via pretreatment based on Oxone® oxidation2017In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 22, no 12, article id 2177Article in journal (Refereed)
    Abstract [sv]

    Softwood sulfite bleached cellulose pulp was oxidized with Oxone (R) and cellulose nanofibers (CNF) were produced after mechanical treatment with a high-shear homogenizer. UV-vis transmittance of dispersions of oxidized cellulose with different degrees of mechanical treatment was recorded. Scanning electron microscopy (SEM) micrographs and atomic force microscopy (AFM) images of samples prepared from the translucent dispersions showed individualized cellulose nanofibers with a width of about 10 nm and lengths of a few hundred nm. All results demonstrated that more translucent CNF dispersions could be obtained after the pretreatment of cellulose pulp by Oxone (R) oxidation compared with the samples produced without pretreatment. The intrinsic viscosity of the cellulose decreased after oxidation and was further reduced after mechanical treatment. Almost translucent cellulose films were prepared from the dispersions of individualized cellulose nanofibers. The procedure described herein constitutes a green, novel, and efficient route to access CNF.

  • 47.
    Ruan, Changqing
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    A green and simple approach for one-pot preparation of an efficient palladium adsorbent based on functionalized 2,3-dialdehyde cellulose2016Conference paper (Refereed)
  • 48.
    Ruan, Changqing
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    A green and simple method for preparation of an efficient palladium adsorbent based on 2,3-dialdehyde cellulose2015In: 4th EPNOE International Polysaccharide Conference 2015, 2015Conference paper (Refereed)
  • 49.
    Ruan, Changqing
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Preparation of Porous 2,3-dialdehyde Cellulose Beads Crosslinked with Chitosan and their Application in Adsorption of Congo Red Dye2018In: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 181, p. 200-207Article in journal (Refereed)
    Abstract [en]

    Micrometer sized 2,3-dialdehyde cellulose (DAC) beads were produced via a recently developed method relying on periodate oxidation of Cladophora nanocellulose. The produced dialdehyde groups and pristine hydroxyl groups provided the DAC beads with a vast potential for further functionalization. The sensitivity of the DAC beads to alkaline conditions, however, limits their possible functionalization and applications. Hence, alkaline-stable and porous cellulose beads were prepared via a reductive amination crosslinking reaction between 2,3-dialdehyde cellulose beads and chitosan. The produced materials were thoroughly characterized with different methods. The reaction conditions, including the amount of chitosan used, conditions for reductive amination, reaction temperature and time, were investigated and the maintained morphology of the beads after exposure to 1 M NaOH (aq.) was verified with SEM. Different washing and drying procedures were used and the results were studied by SEM and BET analysis. Furthermore, FTIR, TGA, EDX, XPS, DLS and elemental analysis were performed to characterize the properties of the prepared beads. Finally, the alkaline-stable porous chitosan cross-linked 2,3-dialdehyde cellulose beads were applied as adsorbent for the dye Congo red. The crosslinked beads displayed fast and high adsorption capacity at pH 2 and good desorption properties at pH 12, providing a promising sorption material.

  • 50.
    Ruan, Changqing
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strömme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Mihranyan, Albert
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Favored Surface-limited Oxidation of Cellulose with Oxone® in Water2017In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 7, no 64, p. 40600-40607Article in journal (Refereed)
    Abstract [en]

    A novel method for favored primary alcohol oxidation of cellulose was developed. Cellulose pulp andCladophora nanocellulose were oxidized in a one-pot procedure by Oxone® (2KHSO5$KHSO4$K2SO4)and efficient reaction conditions were identified. The effects of the reaction on the morphology,viscosity and chemical structure of the products obtained were studied. The primary alcohol groupswere oxidized to carboxyl groups and the content of carboxyl groups was determined byconductometric titration. SEM, capillary-type viscometry and XRD were applied to characterize theproducts and to investigate the influence of oxidation. For the first time, low-cost and stable Oxone®was used as a single oxidant to oxidize cellulose into carboxyl cellulose. The oxidation is an inexpensiveand convenient process to produce carboxylic groups on the surface of the cellulose fibers and to makethe cellulose fibers charged. Particularly, this method can avoid the use of halogens and potentially toxicradicals and constitute a green route to access carboxylated cellulose. Further, sodium bromide could beused as a co-oxidant to the Oxone® and increase the carboxylic acid content by 10–20%. The Oxone®oxidation is a promising method for oxidation of cellulose and might facilitate the production of CNC.

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