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用于设计具有强手性光学活性的对映体纯薄膜的类螺旋烯分子的大规模合成。

Large-Scale Synthesis of Helicene-Like Molecules for the Design of Enantiopure Thin Films with Strong Chiroptical Activity.

作者信息

Bensalah-Ledoux Amina, Pitrat Delphine, Reynaldo Thibault, Srebro-Hooper Monika, Moore Barry, Autschbach Jochen, Crassous Jeanne, Guy Stéphan, Guy Laure

机构信息

Institut Lumière Matière, Université Lyon 1 CNRS UMR5306, Villeurbanne, 69622, France.

Laboratoire de Chimie, Université de Lyon, CNRS, Ecole Normale Supérieure de Lyon, UMR 5182, 46, Allée d'Italie, 69364, Lyon cedex 07, France.

出版信息

Chemistry. 2016 Mar 1;22(10):3333-3346. doi: 10.1002/chem.201504174. Epub 2016 Jan 21.

DOI:10.1002/chem.201504174
PMID:26797752
Abstract

Helicenes are fascinating molecules owing to their unusual properties and applications in many fields from catalysis to organic electronics. Herein, we report a straightforward pathway for the synthesis of helicene-like molecules on a gram scale in an enantiopure form. Thin-film materials with good propagating optical properties and very high chiroptical responses have been grown by using pulsed laser ablation without altering the structure or the enantiopurity of the molecules. Moreover, electronic and vibrational circular dichroism spectroscopies coupled with theoretical calculations enabled some dependences of the chiroptical properties with the structure to be highlighted, for example, effects of rigidification, aromatization, or the state of matter (liquid versus solid).

摘要

螺旋烯是一类迷人的分子,因其独特的性质以及在从催化到有机电子学等众多领域的应用。在此,我们报道了一种以对映体纯形式在克级规模上合成类螺旋烯分子的直接方法。通过脉冲激光烧蚀制备了具有良好传播光学性质和非常高的圆二色性响应的薄膜材料,且未改变分子的结构或对映体纯度。此外,电子圆二色光谱和振动圆二色光谱与理论计算相结合,能够突出一些圆二色性性质与结构的相关性,例如,刚性化、芳构化或物态(液体与固体)的影响。

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