Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films

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Authors

JAKUBEC Martin NOVÁK David ZATLOUKALOVÁ Martina CÍSAŘOVÁ Ivana CIBULKA Radek FAVEREAU Ludovic CRASSOUS Jeanne CYTRYNIAK Adrianna BILEWICZ Renata HRBÁČ Jan STORCH Jan ŽÁDNÝ Jaroslav VACEK Jan

Year of publication 2021
Type Article in Periodical
Magazine / Source ChemPlusChem
MU Faculty or unit

Faculty of Science

Citation
Web https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202100092
Doi http://dx.doi.org/10.1002/cplu.202100092
Keywords flavins; helicenes; lipidic cubic phases; redox behavior; thin layers
Description 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.
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