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

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6407-6410
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number17
DOIs
Publication statusPublished - 2013 May 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Metastable liquid crystal as time-responsive reaction medium: Aging-induced dual enantioselective control'. Together they form a unique fingerprint.

  • Cite this