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Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films
ChemPlusChem ( IF 3.4 ) Pub Date : 2021-05-11 , DOI: 10.1002/cplu.202100092
Martin Jakubec 1 , David Novák 2 , Martina Zatloukalová 2 , Ivana Císařová 3 , Radek Cibulka 4 , Ludovic Favereau 5 , Jeanne Crassous 5 , Adrianna Cytryniak 6 , Renata Bilewicz 6 , Jan Hrbáč 7 , Jan Storch 1 , Jaroslav Žádný 1 , Jan Vacek 2
Affiliation  

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.

中文翻译:

黄素-螺旋烯两亲杂化物:表面支撑薄膜的合成、表征和制备

这项工作报告了黄素 [7] helicene 1(黄素-[7] helicene 共轭物)的制备和结构表征,随后在水环境或有机相中的分子水平上,在超分子水平上进行了表征。聚合物层的形式,并且还嵌入脂质中间相环境中,以研究这种混合体相对于其母体分子的所得特性。黄素苯并[ g ]蝶呤- 2,4-二酮(异恶嗪)因其光活性和可逆的氧化还原行为而被选择用于缀合。化合物 1由 2-亚硝基[6]螺旋烯和 6-甲氨基-3-甲基尿嘧啶制备,并使用常见的结构和光谱工具表征:圆二色性 (CD)、圆偏振发光 (CPL) 光谱、循环伏安法 (CV) 和 DFT量子计算。此外,还开发了一种方法,可以将1 种对映异构体加载到内部纳米结构的脂质(1-单油酸甘油酯)基质中。
更新日期:2021-07-02
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