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

    16 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

    Fingerprint

    Liquid Crystals
    Liquid crystals
    Aging of materials
    Enantioselectivity
    Isomers
    Isothermal annealing
    Acids
    Biological systems
    Ultraviolet Rays
    Ultraviolet radiation
    Amines
    Salts
    Annealing
    Crystalline materials

    ASJC Scopus subject areas

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

    Cite this

    Metastable liquid crystal as time-responsive reaction medium : Aging-induced dual enantioselective control. / Ishida, Yasuhiro; Matsuoka, Yuki; Kai, Yukiko; Yamada, Kuniyo; Nakagawa, Kenta; Asahi, Toru; Saigo, Kazuhiko.

    In: Journal of the American Chemical Society, Vol. 135, No. 17, 01.05.2013, p. 6407-6410.

    Research output: Contribution to journalArticle

    Ishida, Yasuhiro ; Matsuoka, Yuki ; Kai, Yukiko ; Yamada, Kuniyo ; Nakagawa, Kenta ; Asahi, Toru ; Saigo, Kazuhiko. / Metastable liquid crystal as time-responsive reaction medium : Aging-induced dual enantioselective control. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 17. pp. 6407-6410.
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