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Jakubec M, Novák D, Zatloukalová M, et al. Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films. Chempluschem. 2021;86(7):982-990doi: 10.1002/cplu.202100092.
Jakubec, M., Novák, D., Zatloukalová, M., Císařová, I., Cibulka, R., Favereau, L., Crassous, J., Cytryniak, A., Bilewicz, R., Hrbáč, J., Storch, J., Žádný, J., & Vacek, J. (2021). Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films. ChemPlusChem, 86(7), 982-990. https://doi.org/10.1002/cplu.202100092
Jakubec, Martin, et al. "Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films." ChemPlusChem vol. 86,7 (2021): 982-990. doi: https://doi.org/10.1002/cplu.202100092
Jakubec M, Novák D, Zatloukalová M, Císařová I, Cibulka R, Favereau L, Crassous J, Cytryniak A, Bilewicz R, Hrbáč J, Storch J, Žádný J, Vacek J. Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films. Chempluschem. 2021 May 11;86(7):982-990. doi: 10.1002/cplu.202100092. Epub 2021 May 11. PMID: 33977667.
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Chempluschem. 2021 May 11;86(7):982-990. doi: 10.1002/cplu.202100092. Epub 2021 May 11.

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

ChemPlusChem

Martin Jakubec, David Novák, Martina Zatloukalová, Ivana Císařová, Radek Cibulka, Ludovic Favereau, Jeanne Crassous, Adrianna Cytryniak, Renata Bilewicz, Jan Hrbáč, Jan Storch, Jaroslav Žádný, Jan Vacek

Affiliations

  1. Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v.v.i., Rozvojová 135, 165 02, Prague 6, Czech Republic.
  2. Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hn?votínská 3, 775 15, Olomouc, Czech Republic.
  3. Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 128 40, Prague 2, Czech Republic.
  4. Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 166 28, Prague, Czech Republic.
  5. Univ. Rennes, CNRS, ISCR-UMR 6226, Campus de Beaulieu, 35042, Rennes Cedex, France.
  6. Faculty of Chemistry, University of Warsaw, Pasteura 1, Warsaw, 02-093, Poland.
  7. Institute of Chemistry, Masaryk University, Kamenice 5, Brno, 725 00, Czech Republic.

PMID: 33977667 DOI: 10.1002/cplu.202100092

Abstract

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.

© 2021 Wiley-VCH GmbH.

Keywords: flavins; helicenes; lipidic cubic phases; redox behavior; thin layers

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