A Chiral Recognition System Orchestrated by Self-Assembly: Molecular Chirality, Self-Assembly Morphology, and Fluorescence Response

Takao Noguchi, Bappaditya Roy, Daisuke Yoshihara, Junji Sakamoto, Tatsuhiro Yamamoto, Seiji Shinkai

研究成果: Contribution to journalArticle

19 引用 (Scopus)

抜粋

The newly developed oligophenylenevinylene (OPV)-based fluorescent (FL) chiral chemosensor (OPV-Me) for the representative enantiomeric guest, 1,2-cyclohexanedicarboxylic acid (1,2-CHDA: RR- and SS-form) showed the high chiral discrimination ability, resulting in the different aggregation modes of OPV-Me self-assembly: RR-CHDA directed the fibrous supramolecular aggregate, whereas SS-CHDA directed the finite aggregate. The consequent FL intensity toward RR-CHDA was up to 30 times larger than that toward SS-CHDA. Accordingly, highly enantioselective recognition was achieved. Application to the chirality sensing was also possible: OPV-Me exhibited a linear relationship between the FL intensity and the enantiomeric excess through the morphological development of stereocomplex aggregates. These results clearly show that the chiral recognition ability is manifested by the amplification cascade of the chirality difference through self-assembly.

元の言語英語
ページ(範囲)12518-12522
ページ数5
ジャーナルAngewandte Chemie - International Edition
56
発行部数41
DOI
出版物ステータス出版済み - 1 1 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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