Flavin‐Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface‐Supported Films
| Autor: | Adrianna Cytryniak, Renata Bilewicz, Jan Storch, Jeanne Crassous, Radek Cibulka, Ivana Císařová, Martin Jakubec, Jan Vacek, Jan Hrbac, David Novak, Ludovic Favereau, Martina Zatloukalová, Jaroslav Žádný |
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| Přispěvatelé: | Institute of Chemical Process Fundamentals (ICPF), Czech Academy of Sciences [Prague] (CAS), Palacky University Olomouc, Charles University [Prague] (CU), University of Chemistry and Technology Prague (UCT Prague), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), University of Warsaw (UW), Masaryk University [Brno] (MUNI), Palacky University [RVO 61989592], Ministry of Education, Youth and Sports (MEYS, Czech Republic) [IGA_LF_2020_022], Czech Science Foundation Grant Agency of the Czech Republic [20-19353S], MEYS [CZ.02.2.69/0.0/0.0/16_027/0008482], project \'e-Infrastruktura CZ\' within the program \'Projects of Large Research, Development and Innovations Infrastructures\' within the program \'Projects of Large Research, Development and Innovations Infrastructures\' [eINFRA LM2018140], Institute of Chemical Process Fundamentals of the ASCR, Czech Republic, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA) |
| Rok vydání: | 2021 |
| Předmět: |
Circular dichroism
thin layers lipidic cubic phases [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Chemistry Supramolecular chemistry Mesophase General Chemistry Flavin group 010402 general chemistry flavins 01 natural sciences 0104 chemical sciences helicenes [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry Crystallography chemistry.chemical_compound Helicene Amphiphile [CHIM]Chemical Sciences Molecule Cyclic voltammetry redox behavior |
| Zdroj: | ChemPlusChem ChemPlusChem, 2021, 86 (7), pp.982-990. ⟨10.1002/cplu.202100092⟩ ChemPlusChem, Wiley, 2021, ⟨10.1002/cplu.202100092⟩ |
| ISSN: | 2192-6506 |
| Popis: | International audience; This work reports on the preparation and structural characterization of flavo[7]helicene 1 (flavin-[7]helicene conjugate), which was subsequently characterized at the molecular level in either an aqueous environment or an organic phase, at the supramolecular level in the form of polymeric layers, and also embedded in a lipidic mesophase environment to study the resulting properties of such a hybrid relative to its parent molecules. The flavin benzo[g]pteridin-2,4-dione (isoalloxazine) was selected for conjugation because of its photoactivity and reversible redox behavior. Compound 1 was prepared from 2-nitroso[6]helicene and 6-methylamino-3-methyluracil, and characterized using common structural and spectroscopic tools: circular dichroism (CD), circularly polarized luminescence (CPL) spectroscopy, cyclic voltammetry (CV), and DFT quantum calculations. In addition, a methodology that allows the loading of 1 enantiomers into an internally nanostructured lipid (1-monoolein) matrix was developed. |
| Databáze: | OpenAIRE |
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