Metastable liquid crystal as time-responsive reaction medium: Aging-induced dual enantioselective control

Yasuhiro Ishida*, Yuki Matsuoka, Yukiko Kai, Kuniyo Yamada, Kenta Nakagawa, Toru Asahi, Kazuhiko Saigo

*この研究の対応する著者

研究成果査読

25 被引用数 (Scopus)

抄録

A metastable liquid crystal (LC) was found to serve as a time-responsive reaction medium, in which the enantioselectivity of a photoreaction was perfectly switched through isothermal annealing of the reaction system. When the LC salt of an enantiopure amine with a photoreactive acid was irradiated with UV/vis light, in situ photodimerization of the acid moiety proceeded smoothly to afford the (+)-isomer of the photodimer with high enantioselectivity (+86% ee). In contrast, photoirradiation of an aged sample, isothermally annealed for 20 h, gave predominantly the (-)-isomer (-94% ee). Systematic studies revealed that the reversal in selectivity originated from metastability of the LC system, which gradually transformed into a crystalline phase during annealing. This finding demonstrates the potential use of metastable aggregates as dynamic time-responsive media, reminiscent of biological systems.

本文言語English
ページ(範囲)6407-6410
ページ数4
ジャーナルJournal of the American Chemical Society
135
17
DOI
出版ステータスPublished - 2013 5 1

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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