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  • 1.
    Bhimpuria, Rohan
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Baddigam, Kiran Reddy
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Xu, Felix
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Wells, Jordann A. L.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Synthesis of styrene, phenyl acrylate and allyloxyphenyl-functionalized porphyrins, and preliminary exploration of their utility for assembling multiple porphyrin units2023In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 27, no 07N10, p. 1398-1408Article in journal (Refereed)
    Abstract [en]

    Three free-base and two Zn(II) porphyrins carrying one alkene-substituted meso-aryl group and three solubilizing pentyl groups were prepared via mixed aldehyde-type syntheses. A meso p-allyloxyphenyl porphyrin was obtained via the corresponding 5-(p-allyloxyphenyl) dipyrromethane. The porphyrins were fully characterized using a combination of NMR spectroscopy, high-resolution mass spectrometry, and UV-Vis absorption and emission spectroscopies. Two of the free-base porphyrins were heated in the presence of AIBN or benzoyl peroxide as the initiator. The major isolated products of these reactions contained two porphyrin units based on the results of MALDI-MS and H-1 NMR analysis data, which was supported by the results of FTIR, UV-Vis absorption and emission spectroscopies, and gel permeation and liquid chromatographies. Additionally, the acrylamide-functionalized porphyrin could be attached to a polylysine scaffold under basic conditions. These results suggest that the olefinic handle can be used to assemble structures containing multiple porphyrinic macrocycles.

  • 2. Fryxelius, Jacob
    et al.
    Eilers, Gerriet
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Feyziyev, Yashar
    Magnuson, Ann
    Sun, Licheng
    Lomoth, Reiner
    Synthesis and redox properties of a [meso-tris(4-nitrophenyl) corrolato]Mn(III) complex.2005In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, no 9(6), p. 379-386Article in journal (Refereed)
  • 3.
    Gao, Shimin
    et al.
    East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Li, Chengjie
    East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Baryshnikov, Glib
    KTH Royal Inst Technol, Sch Biotechnol, Div Theoret Chem & Biol, SE-10691 Stockholm, Sweden.;Bohdan Khmelnytsky Natl Univ, Dept Chem & Nanomat Sci, UA-18031 Cherkassy, Ukraine..
    Ågren, Hans
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy.
    Li, Qizhao
    East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Xie, Yongshu
    East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Syntheses of thiophene appended N-confused phlorin isomers2021In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 25, no 10N12, p. 997-1003Article in journal (Refereed)
    Abstract [en]

    A doubly confused thiapentapyrrane NSP-5 was synthesized by acid-catalysed condensation. Subsequent oxidation with DDQ did not afford the expected thiasapphyrin-like product. Instead, two tetrapyrrolic macrocycles, i.e. neo-N-confused phlorin (1) and N-confused phlorin-II (2) were obtained in the yields of 14% and 18%, respectively. The compounds were characterized by NMR, HRMS, and X-ray diffraction analyses. Single crystal structures clearly reveal that the thienyl units are not embedded into the macrocycles, but appended as meso-substituents, and the C-meso-N and C-meso-C-beta cyclization modes can be clearly revealed by the crystal structures of 1 and 2, respectively. The observation that the thienyl unit is not involved in oxidative cyclization may be related to the relatively low reactivity of the thiophene moiety compared with the more electron-rich pyrrole unit. These results indicate that oxidative cyclization of linear thiaoligopyrranes containing terminal thiophene units may be developed as an effective approach for synthesizing nonconjugated macrocycles like phlorin analogues.

  • 4.
    Huang, Yanping
    et al.
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Fu, Yating
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Zhu, Bin
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Baryshnikov, Glib
    Linköping Univ, Dept Sci & Technol, Lab Organ Elect, SE-60174 Norrköping, Sweden..
    Sun, Hao-Ling
    Beijing Normal Univ, Dept Chem, Beijing Key Lab Energy Convers & Storage Mat, Beijing 100875, Peoples R China..
    Sha, Feng
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Li, Chengjie
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Wu, Xin-Yan
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Ågren, Hans
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Chemical and Bio-Molecular Physics.
    Li, Qizhao
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Xie, Yongshu
    East China Univ Sci & Technol, Key Lab Adv Mat & Inst Fine Chem, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Syntheses and characterization of dithienyl-blocked hexapyrrin and its mononuclear complexes2023In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 27, no 07N10, p. 1089-1096Article in journal (Refereed)
    Abstract [en]

    With the purpose to develop long chain-conjugated oligopyrrin-like compounds and their metal complexes, and thus achieve tunable near-infrared absorption, a dithienyl-blocked hexapyrrane S-2-P-6 was synthesized by acid-catalyzed [2+4+2] condensation, followed by oxidation with DDQ to afford dithiaoctapyrrin 1, and its mononuclear metal complexes 1-Cu and 1-Zn were synthesized by treating 1 with Cu(II) and Zn(II) acetates. All the compounds were systematically characterized by NMR/EPR, and HRMS. The crystal structures revealed that 1 adopts a double hook-like conformation. Whereas, both complexes 1-Cu and 1-Zn adopt spiral-hook hybrid conformations, showing smaller interplanar angles between the rings within the spiral part, compared with those in the hook-like counterpart of molecule 1, which is favorable for red-shifting the absorption. As expected, the absorption band edges for complexes 1-Cu and 1-Zn are red-shifted to ca. 1560 nm, compared with that of 1260 nm observed for 1.

  • 5. Maaza, Malik
    et al.
    Mongwaketsi, Nametso
    Genene, Mola
    Gebresenbut, Girma Hailu
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Structural Chemistry.
    Garab, Gyozo
    Sahraoui, Bouchta
    Hamidi, Dalila
    Nonlinear photonics properties of porphyrins nanocomposites and self-assembled porphyrins2012In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 16, no 7-8, p. 985-995Article in journal (Refereed)
    Abstract [en]

    Two major reasons limit porphyrins photonic applications: (i) the difficulty of handling them in liquid solutions and (ii) their degradation with long exposure to light. This necessitates the use of appropriate solid matrices to host the porphyrin compounds such as Nafion (117), a stable and inert ion exchange polymer. The first part of this publication confirms such a possibility. In addition to their effective NLO properties, an enhancement of the Soret and Q-bands' absorbance width have been observed by blending three different porphyrin molecules in the Nafion column matrix membrane. This is an important development towards achieving efficient photon-harvesting medium for possible application in photonic devices. The second part of this contribution reports on the self-assembly/molecular recognition of a specific class of porphyrins giving rise to tubular nano-systems with potential THG nonlinear properties.

  • 6.
    Rana, Anup
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström. Univ Hyderabad, Sch Chem, Hyderabad 500046, India;Univ Hyderabad, ACRHEM, Hyderabad 500046, India.
    Sahoo, Sipra Sucharita
    Univ Hyderabad, Sch Chem, Hyderabad 500046, India.
    Panda, Pradeepta K.
    Univ Hyderabad, Sch Chem, Hyderabad 500046, India;Univ Hyderabad, ACRHEM, Hyderabad 500046, India.
    β-Octaalkoxyporphyrins: Versatile fluorometric sensors towards nitrated explosives2019In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 23, no 3, p. 287-295Article in journal (Refereed)
    Abstract [en]

    Real time detection of explosive residues is important to mitigate increasing security threats. Therefore, systematic studies are essential to optimize the performance of sensors. In this work, we have explored β-octamethoxyporphyrin and β-octabutoxyporphyrin to evaluate the effect of alkoxy groups in solution and in vapor phase sensing of nitrated explosives. Our systematic studies revealed a marked difference in sensitivity of these free-base porphyrins in solution state and vapor phase sensing of nitrated explosives simply by modulation of alkyl chain lengths. Alkoxyporphyrins exhibit very good sensitivity towards not only nitro aromatics but also alkyl nitro explosive taggants compared to β-octaethylporphyrin. Therefore, alkoxyporphyrins may act as versatile fluorescence turn-off based chemical sensors for nitrated explosives.

  • 7.
    Sollert, Carina
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Kócsi, Dániel
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Jane, Reuben T.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Orthaber, Andreas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    C-glycosylated pyrroles and their application in dipyrromethane and porphyrin synthesis2021In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 25, no 7-8, p. 741-755Article in journal (Refereed)
    Abstract [en]

    Pyrrole C-glycosylated in either the 2- or the 3-position could be prepared by the acid-catalyzed reaction between trichloroacetimidate glycosyl donors and pyrrole, or N-phenyl-trifluoroacetimidate glucosyl donor and N-TIPS pyrrole, respectively. Pyrroles carrying glucose, mannose, galactose and lactose in the 2-position, and glucose in the 3-position were obtained. The configurations of the products could be assigned using a combination of 1D and 2D NMR spectroscopy. A number of undesired background reactions yielding a variety of stereo- and regioisomers were identified; in several cases these could be eliminated. Glycosylpyrroles could be incorporated into mono- and diglycosylated dipyrromethanes, a diglycosylated BODIPY dye, and a monoglycosylated Zn(II) porphyrin without damaging the sugar unit.

  • 8.
    Witkowski, Nadine
    et al.
    Sorbonne Univ, Inst Nanosci Paris, UMR CNRS 7588, 4 Pl Jussieu, F-75005 Paris, France.
    Lüder, Johann
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory. Natl Sun Yat Sen Univ, Dept Mat & Optoelect Sci, Kaohsiung 80424, Taiwan.
    Bidermane, Ieva
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Molecular and Condensed Matter Physics. Sorbonne Univ, Inst Nanosci Paris, UMR CNRS 7588, 4 Pl Jussieu, F-75005 Paris, France.
    Farronato, Mattia
    Sorbonne Univ, Inst Nanosci Paris, UMR CNRS 7588, 4 Pl Jussieu, F-75005 Paris, France.
    Prevot, Geoffroy
    Sorbonne Univ, Inst Nanosci Paris, UMR CNRS 7588, 4 Pl Jussieu, F-75005 Paris, France.
    Bouvet, Marcel
    Univ Bourgogne Franche Comte, Inst Chim Mol, Univ Bourgogne, CNRS,UMR 6302, F-21078 Dijon, France.
    Puglia, Carla
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Molecular and Condensed Matter Physics.
    Brena, Barbara
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Materials Theory.
    Grafting, self-organization and reactivity of double-decker rare-earth phthalocyanine2019In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 23, no 11-12, p. 1523-1534Article in journal (Refereed)
    Abstract [en]

    Unveiling the interplay of semiconducting organic molecules with their environment, such as inorganic materials or atmospheric gas, is the first step to designing hybrid devices with tailored optical, electronic or magnetic properties. The present article focuses on a double-decker lutetium phthalocyanine known as an intrinsic semiconducting molecule, holding a Lu ion in its center, sandwiched between two phthalocyanine rings. Carrying out experimental investigations by means of electron spectroscopies, X-ray diffraction and scanning probe microscopies together with advanced ab initio computations, allows us to unveil how this molecule interacts with weakly or highly reactive surfaces. Our studies reveal that a molecule-surface interaction is evidenced when molecules arc deposited on bare silicon or on gold surfaces together with a charge transferred from the substrate to the molecule, affecting to a higher extent the lower ring of the molecule. A new packing of the molecules on gold surfaces is proposed: an eclipse configuration in which molecules are flat and parallel to the surface, even for thick films of several hundreds of nanometers. Surprisingly, a robust tolerance of the double-decker phthalocyanine toward oxygen molecules is demonstrated, leading to weak chemisorption of oxygen below 100 K.

  • 9.
    Xiong, Ruisheng
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Arkhypchuk, Anna I.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
    Attempted syntheses of N-confused hydroporphyrins through modified Lindsey routes2019In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 23, no 4-5, p. 589-598Article in journal (Refereed)
    Abstract [en]

    Unlike N-confused porphyrins which are well-known and extensively studied tetrapyrroles, N-confused hydroporphyrins are almost unknown, largely because so far they have resisted attempts at rational synthesis. Here, we report our efforts towards the total synthesis of N-confused hydroporphyrins. We have prepared N-confused building blocks analogous to the non-N-confused substrates in the Lindsey synthesis of sparsely substituted chlorins. We have systematically flipped the A, B and C pyrrole rings in the dipyrrolic precursors of the target N-confused macrocycles, preparing in total an N-confused "Western half' (tetrahydrodipyrrin) and two N-confused "Eastern halves" (brominated formyldipyrromethanes). These were subjected to a range of cyclization conditions. While we successfully isolated and identified three macrocyclic products, none of these proved to be the desired N-confused hydroporphyrin.

  • 10.
    Yang, Zhen
    et al.
    East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Baryshnikov, Glib
    Linköping Univ, Dept Sci & Technol, Lab Organ Elect, SE-60174 Norrköping, Sweden..
    Sha, Feng
    East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Li, Chengjie
    East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Wu, Xinyan
    East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Ågren, Hans
    Uppsala University, Disciplinary Domain of Science and Technology, Physics, Department of Physics and Astronomy, Chemical and Bio-Molecular Physics.
    Xie, Yongshu
    East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Li, Qizhao
    East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China..
    Synthesis and coordination of a dipyrrin appended N-confused porphyrin2023In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 27, no 1, p. 285-292Article in journal (Refereed)
    Abstract [en]

    A hexapyrrane P6 with a terminal N-confused pyrrole was synthesized by acid-catalyzed [3+3] condensation followed by oxidation with DDQ, which did not afford the expected N-confused hexaphyrin. In stead, a rearranged product, i.e., α-dipyrrin appended N-confused porphyrin 1 was obtained in a yield of 46%. Chelation of 1 with Pt(II) afforded the peripheral complex 1-Pt, which was further coordinated with Rh(I) in the cavity to afford the corresponding bimetallic complex 1-Pt-Rh. Both 1-Pt and 1-Pt-Rh exhibit split Soret-like bands and noticeable Q-like bands tailing to the NIR region up to ca. 1200 nm. Single crystal X-ray diffraction analyses of 1 and 1-Pt revealed that the peripheral coordination of Pt(II) slightly modifies the interplanar angle between the porphyrin macrocycle and the dipyrrin unit, which may modulate the absorption spectra. The results of this work compose an interesting example of synthesizing porphyrinoids appended with conjugated peripheral chains by the oxidative ring closure reaction of an oligopyrrane containing a terminal N-confused pyrrole, and such compounds may be used for both inner and peripheral coordination to afford complexes with tunable NIR absorption.

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