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Norrehed, S., Karlsson, C., Light, M. E., Thapper, A., Huang, P. & Gogoll, A. (2019). Formation of persistent organic diradicals from N,N'-diphenyl-3,7- diazacyclooctanes. Monatshefte fuer Chemie, 150(1), 77-84
Open this publication in new window or tab >>Formation of persistent organic diradicals from N,N'-diphenyl-3,7- diazacyclooctanes
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2019 (English)In: Monatshefte fuer Chemie, ISSN 0026-9247, E-ISSN 1434-4475, Vol. 150, no 1, p. 77-84Article in journal (Refereed) Published
Abstract [en]

N,N'-Diphenyl-3,7-diazacyclooctane and structurally related N,N'-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C–C coupling reaction to produce dication–diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.

Place, publisher, year, edition, pages
Vienna: Springer, 2019
Keywords
Biaryls, Crystal structure, Heterocycles, Oxidative coupling, biradicals
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-364531 (URN)10.1007/s00706-018-2298-4 (DOI)000454953600009 ()
Funder
Swedish Research Council
Available from: 2018-10-29 Created: 2018-10-29 Last updated: 2019-01-28Bibliographically approved
Olsson, S. K., Dahlstrand, C. & Gogoll, A. (2018). Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding. Dalton Transactions, 47(33), 11572-11585
Open this publication in new window or tab >>Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding
2018 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 47, no 33, p. 11572-11585Article in journal (Refereed) Published
Abstract [en]

By systematic measurements we have evaluated a series of tetraphenyl metalloporphyrins and halogenated tetraphenyl metalloporphyrin derivatives for binding to ligands with oxygen containing functional groups, using methanol, acetic acid and acetone as examples. Experimental binding constants identified three metalloporphyrins with good binding to all three ligands: MgTPFPP, MgTPPBr8 and ZnTPPBr8 as well as a range of porphyrins binding to select ligands. Based on these results the optimal porphyrins can be selected for the desired binding interactions. We also show how to use DFT calculations to evaluate the potential binding between a metalloporphyrin and a ligand, which is deduced from free energies of binding ΔG, charge transfer ΔQ, and change of metal spin state. Computations on unsubstituted porphyrins in lieu of tetraphenyl porphyrin systems yield reliable predictions of binding interactions with good correlation to the corresponding experimental data. The calculations have also yielded interesting insights into the effect of halogenation in the β-position on the binding to ligands with oxygen containing functional groups.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2018
Keywords
Porphyrins, DFT, host-guest
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-359830 (URN)10.1039/c8dt02432d (DOI)000442509700031 ()30087966 (PubMedID)
Funder
Swedish Research Council, 621-2012-3379Carl Tryggers foundation , 16:156Swedish National Infrastructure for Computing (SNIC), 2018/3-240National Supercomputer Centre (NSC), Sweden, SNIC 2018/3-240
Available from: 2018-09-06 Created: 2018-09-06 Last updated: 2018-10-29Bibliographically approved
Olsson, S. K., Schäfer, C., Blom, M. & Gogoll, A. (2018). Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer. ChemPlusChem, 83, 1169-1178
Open this publication in new window or tab >>Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer
2018 (English)In: ChemPlusChem, ISSN 2192-6506, Vol. 83, p. 1169-1178Article in journal (Refereed) Published
Abstract [en]

A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 :10 to 1: 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1:2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlagsgesellschaft, 2018
Keywords
bis-porphyrin tweezers, conformation analysis, exciton-coupled circular dichroism, host-guest systems, molecular modeling
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-371629 (URN)10.1002/cplu.201800564 (DOI)000454527200013 ()
Funder
Swedish Research Council, 621-2012-3379Carl Tryggers foundation , CTS 16 : 156
Available from: 2018-12-21 Created: 2018-12-21 Last updated: 2019-01-25Bibliographically approved
Yang, D., Zhao, J., Yu, L., Lin, X., Zhang, W., Ma, H., . . . Wu, B. (2017). Air- and Light-Stable P-4 and As-4 within an Anion-Coordination-Based Tetrahedral Cage. Journal of the American Chemical Society, 139(16), 5946-5951
Open this publication in new window or tab >>Air- and Light-Stable P-4 and As-4 within an Anion-Coordination-Based Tetrahedral Cage
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2017 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 139, no 16, p. 5946-5951Article in journal (Refereed) Published
Abstract [en]

In contrast to the stable dinitrogen molecule, white phosphorus (P-4) and yellow arsenic (As-4) are very reactive allotropic modifications of these two heavier pnictogen elements, which has greatly hampered the study of their properties and applications. Thus, the safe storage and transport of them is imperative. Supramolecular caged structures are one of the most efficient approaches for the encapsulation and stabilization of reactive species; however, their use in the P-4 and As-4 chemistry is very rare. In the current work, we demonstrate a new design strategy for constructing finite cages and including guests based on anion coordination chemistry. The phosphate-coordination-based tetrahedral cages can readily accommodate the tetrahedral guests P-4 and As-4, which is facilitated by the shape and size complementarity as well as favorable sigma-pi and lone-pair-pi interactions. Moreover, the latter case represents the first example of As-4 inclusion in a well-defined tetrahedral cage.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC, 2017
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-322723 (URN)10.1021/jacs.7b01890 (DOI)000400321500053 ()28335592 (PubMedID)
Available from: 2017-05-29 Created: 2017-05-29 Last updated: 2017-05-29Bibliographically approved
Sterby, M., Emanuelsson, R., Huang, X., Gogoll, A., Strömme, M. & Sjödin, M. (2017). Characterization of PEDOT-Quinone Conducting Redox Polymers for Water Based Secondary Batteries. Electrochimica Acta, 235, 356-364
Open this publication in new window or tab >>Characterization of PEDOT-Quinone Conducting Redox Polymers for Water Based Secondary Batteries
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2017 (English)In: Electrochimica Acta, ISSN 0013-4686, E-ISSN 1873-3859, Vol. 235, p. 356-364Article in journal (Refereed) Published
Abstract [en]

Lithium-ion technologies show great promise to meet the demands that the transition towards renewable energy sources and the electrification of the transport sector put forward. However, concerns regarding lithium-ion batteries, including limited material resources, high energy consumption during production, and flammable electrolytes, necessitate research on alternative technologies for electrochemical energy storage. Organic materials derived from abundant building blocks and with tunable properties, together with water based electrolytes, could provide safe, inexpensive and sustainable alternatives. In this study, two conducting redox polymers based on poly(3,4-ethylenedioxythiophene) (PEDOT) and a hydroquinone pendant group have been synthesized and characterized in an acidic aqueous electrolyte. The polymers were characterized with regards to kinetics, pH dependence, and mass changes during oxidation and reduction, as well as their conductance. Both polymers show redox matching, i.e. the quinone redox reaction occurs within the potential region where the polymer is conducting, and fast redox conversion that involves proton cycling during pendant group redox conversion. These properties make the presented materials promising candidates as electrode materials for water based all-organic batteries.

Keywords
Conducting Redox Polymer, Quinone, Organic Batteries, Proton Batteries, Redox Matching
National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-319049 (URN)10.1016/j.electacta.2017.03.068 (DOI)000398330200042 ()
Funder
Swedish Foundation for Strategic Research Swedish Research CouncilCarl Tryggers foundation Swedish Energy AgencyEU, Horizon 2020, 644631
Available from: 2017-03-30 Created: 2017-03-30 Last updated: 2017-05-12Bibliographically approved
Sjödin, M., Emanuelsson, R., Sterby, M., Strietzel, C., Yang, L., Huang, H., . . . Strömme, M. (2017). Conducting Redox Polymer Based Batteries. In: : . Paper presented at Organic Battery Days, Uppsala, June 8-9, 2017..
Open this publication in new window or tab >>Conducting Redox Polymer Based Batteries
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2017 (English)Conference paper, Oral presentation with published abstract (Refereed)
National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-334410 (URN)
Conference
Organic Battery Days, Uppsala, June 8-9, 2017.
Available from: 2017-11-23 Created: 2017-11-23 Last updated: 2017-12-13Bibliographically approved
Yang, L., Huang, X., Mamedov, F., Zhang, P., Gogoll, A., Strömme, M. & Sjödin, M. (2017). Conducting redox polymers with non-activated charge transport properties. Physical Chemistry, Chemical Physics - PCCP, 19(36), 25052-25058
Open this publication in new window or tab >>Conducting redox polymers with non-activated charge transport properties
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2017 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 19, no 36, p. 25052-25058Article in journal (Refereed) Published
Abstract [en]

Non-activated charge transport has been demonstrated in terephthalate-functionalized conducting redox polymers. The transition from a temperature-activated conduction mechanism to a residual scattering mechanism was dependent on the doping level. The latter mechanism is associated with apparent negative activation barriers to charge transport and is generally found in polymer materials with a high degree of order. Crystallographic data, however, suggested a low degree of order in this polymer, indicating the existence of interconnected crystal domains in the predominantly amorphous polymer matrix through which the charge was transported. We have thus shown that the addition of bulky pendant groups to conducting polymers does not prevent efficient charge transport via the residual scattering mechanism with low barriers to charge transport.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2017
National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-304625 (URN)10.1039/c7cp03939e (DOI)000411606200067 ()28879367 (PubMedID)
Funder
Swedish Research CouncilSwedish Foundation for Strategic Research Stiftelsen Olle Engkvist ByggmästareEU, Horizon 2020, 64431Swedish Energy Agency
Available from: 2016-10-06 Created: 2016-10-06 Last updated: 2018-06-04Bibliographically approved
Sjödin, M., Emanuelsson, R., Sterby, M., Åkerlund, L., Huang, H., Huang, X., . . . Strömme, M. (2017). Organic Batteries Based on Quinone-Substituted Conducting Polymers. In: : . Paper presented at The 17th IUPAC International Symposium on MacroMolecular Complexes (MMC-17), Tokyo, August 28-31, 2017..
Open this publication in new window or tab >>Organic Batteries Based on Quinone-Substituted Conducting Polymers
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2017 (English)Conference paper, Oral presentation with published abstract (Refereed)
National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-334414 (URN)
Conference
The 17th IUPAC International Symposium on MacroMolecular Complexes (MMC-17), Tokyo, August 28-31, 2017.
Available from: 2017-11-23 Created: 2017-11-23 Last updated: 2017-11-27Bibliographically approved
Huang, H., Karlsson, C., Mamedov, F., Strömme, M., Gogoll, A. & Sjödin, M. (2017). Polaron Disproportionation Charge Transport in a Conducting Redox Polymer. The Journal of Physical Chemistry C, 121(24), 13078-13083
Open this publication in new window or tab >>Polaron Disproportionation Charge Transport in a Conducting Redox Polymer
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2017 (English)In: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 121, no 24, p. 13078-13083Article in journal (Refereed) Published
Abstract [en]

Herein we report a mechanistic study of the charge transport in poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole by conductance measurements at various temperatures performed in situ during doping of the polypyrrole backbone in contact with an aqueous electrolyte. Charge transport was found to occur by electron hopping with associated electron transfer activation energies in the range of 0.08-0.2 eV. In situ electron paramagnetic resonance experiments indicated polarons as the dominant charge carriers and the charge transport was found to follow a second-order dependence with respect to the number of accumulated charges. Based on the findings, we present a polaron comproportionation/disproportionation model for electron conduction in poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole, thus, providing a complement to existing models for charge propagation in conducting polymers.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC, 2017
National Category
Physical Chemistry Engineering and Technology Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-329648 (URN)10.1021/acs.jpcc.7b03671 (DOI)000404201900013 ()
Funder
Swedish Foundation for Strategic Research Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareSwedish Energy Agency
Available from: 2017-09-26 Created: 2017-09-26 Last updated: 2017-11-25
Huang, H., Karlsson, C., Strømme, M., Gogoll, A. & Sjödin, M. (2017). Synthesis and Characterization of Poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole: investigation on Backbone/Pendant Interactions in a Conducting Redox Polymer. Physical Chemistry, Chemical Physics - PCCP, 19(16), 10427-10435
Open this publication in new window or tab >>Synthesis and Characterization of Poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole: investigation on Backbone/Pendant Interactions in a Conducting Redox Polymer
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2017 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 19, no 16, p. 10427-10435Article in journal (Refereed) Published
Abstract [en]

We herein report the synthesis and electrochemical characterization of poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole, consisting of a polypyrrole backbone derivatized at the beta position by a vinyl-hydroquinone pendant group. The structure of the polymer was characterized by solid state NMR spectroscopy. The interactions between the polypyrrole backbone and the oxidized quinone or reduced hydroquinone pendant groups are probed by several in situ methods. In situ attenuated total reflectance-Fourier transform infrared spectroscopy shows spectroscopic response from both the doping of the polymer backbone and the redox activity of the pendant groups. Using an in situ Electrochemical Quartz Crystal Microbalance we reveal that the polymer doping is unaffected by the pendant group redox chemistry, as opposed to previous reports. Despite the continuous doping the electrochemical conversion from the hydroquinone state to the quinone state results in a significant conductance drop, as observed by in situ conductivity measurements using an InterDigitated Array electrode set-up. Twisting of the conducting polymer backbone as a result of a decreased separation between pendant groups due to π-π stacking in the oxidized state is suggested as the cause of this conductance drop.

National Category
Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-316490 (URN)10.1039/c6cp08736a (DOI)000400117700025 ()28379225 (PubMedID)
Funder
Swedish Foundation for Strategic Research Swedish Research CouncilCarl Tryggers foundation Stiftelsen Olle Engkvist ByggmästareSwedish Energy AgencyEU, Horizon 2020, 644631
Available from: 2017-03-01 Created: 2017-03-01 Last updated: 2017-11-25
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0002-9092-261X

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