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

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)12518-12522
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number41
DOIs
Publication statusPublished - Jan 1 2017

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Chirality
Self assembly
Fluorescence
Amplification
Agglomeration
Acids

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

A Chiral Recognition System Orchestrated by Self-Assembly : Molecular Chirality, Self-Assembly Morphology, and Fluorescence Response. / Noguchi, Takao; Roy, Bappaditya; Yoshihara, Daisuke; Sakamoto, Junji; Yamamoto, Tatsuhiro; Shinkai, Seiji.

In: Angewandte Chemie - International Edition, Vol. 56, No. 41, 01.01.2017, p. 12518-12522.

Research output: Contribution to journalArticle

Noguchi, Takao ; Roy, Bappaditya ; Yoshihara, Daisuke ; Sakamoto, Junji ; Yamamoto, Tatsuhiro ; Shinkai, Seiji. / A Chiral Recognition System Orchestrated by Self-Assembly : Molecular Chirality, Self-Assembly Morphology, and Fluorescence Response. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 41. pp. 12518-12522.
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