CBMN (UMR5248), Univ. Bordeaux-CNRS-IPB, Institut Européen de Chimie et Biologie, 2 rue Escarpit, 33600, Pessac, France.
Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780, Poznan, Poland.
Chemistry. 2021 Jan 13;27(3):1031-1038. doi: 10.1002/chem.202003559. Epub 2020 Dec 3.
Quinoline based aromatic amide foldamers are known to adopt stable folded conformations. We have developed a synthetic approach to produce similar oligomers where all amide bonds, or part of them, have been replaced by an isosteric vinylene group. The results of solution and solid state structural studies show that oligomers exclusively containing vinylene linkages are not well folded, and adopt predominantly flat conformations. In contrast, a vinylene segment flanked by helical oligoamides also folds in a helix, albeit with a slightly lower curvature. The presence of vinylene functions also result in an extension of π-conjugation across the oligomer that may change charge transport properties. Altogether, these results pave the way to foldamers in which both structural control and specific electronic properties may be engineered.
基于喹啉的芳酰胺类折叠物已知可采用稳定的折叠构象。我们已经开发出一种合成方法来制备类似的寡聚物，其中所有的酰胺键或部分酰胺键已被等排的亚乙烯基取代。溶液和固态结构研究的结果表明，仅含有亚乙烯基键的寡聚物折叠效果不佳，主要呈平面构象。相比之下，由螺旋寡酰胺侧翼包围的亚乙烯基片段也会折叠成螺旋，尽管曲率略低。亚乙烯基官能团的存在也会导致整个寡聚物的π 共轭延伸，从而可能改变电荷输运性质。总之，这些结果为可以同时进行结构控制和特定电子性质设计的折叠物铺平了道路。
