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.

Department of Inorganic Chemistry Faculty of Science Charles University Prague Hlavova 2030 128 40 Prague 2 Czech Republic

Department of Medical Chemistry and Biochemistry Faculty of Medicine and Dentistry Palacký University Hněvotínská 3 775 15 Olomouc Czech Republic

Department of Organic Chemistry University of Chemistry and Technology Prague Technická 5 166 28 Prague Czech Republic

Faculty of Chemistry University of Warsaw Pasteura 1 Warsaw 02 093 Poland

Institute of Chemical Process Fundamentals of the Czech Academy of Sciences v v i Rozvojová 135 165 02 Prague 6 Czech Republic

Institute of Chemistry Masaryk University Kamenice 5 Brno 725 00 Czech Republic

Univ Rennes CNRS ISCR UMR 6226 Campus de Beaulieu 35042 Rennes Cedex France

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Lipid-based liquid crystalline materials in electrochemical sensing and nanocarrier technology