Translation of dicarboxylate structural information to fluorometric optical signals through self-assembly of guanidinium-tethered oligophenylenevinylene

Takao Noguchi, Bappaditya Roy, Daisuke Yoshihara, Youichi Tsuchiya, Tatsuhiro Yamamoto, Seiji Shinkai

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Although self-assembly has realized the spontaneous formation of nanoarchitectures, the nanoscopic expression of chemical structural information at the molecular level can alternatively be regarded as a tool to translate molecular structural information with high precision. We have found that a newly developed guanidinium-tethered oligophenylenevinylene exhibits characteristic fluorescence (FL) responses toward L- and meso-tartarate, wherein the different self-assembly modes, termed J- or H-type aggregation, are directed according to the molecular information encoded as the chemical structure. This morphological difference originates from the geometric anti versus gauche conformational difference between L- and meso-tartarate. A similar morphological difference can be reproduced with the geometric C=C bond difference between fumarate and maleate. In the present system, the dicarboxylate structural information is embodied in the inherent threshold concentration of the FL response, the signal-to-noise ratio, and the maximum FL wavelength. These results indicate that self-assembly is meticulous enough to sense subtle differences in molecular information and thus demonstrate the potential ability of self-assembly for the expression of a FL sensory system. Self-assembly married to molecular recognition: A novel assembly-based fluorescence (FL) sensory system exhibits characteristic FL responses toward L- and meso-tartarate, wherein different self-assembly processes are directed according to the molecular structural information (see figure). This utilization of self-assembly substantiates its potential ability to translate molecular information and thus opens up a new avenue of molecular recognition.

Original languageEnglish
Pages (from-to)13938-13944
Number of pages7
JournalChemistry - A European Journal
Volume20
Issue number43
DOIs
Publication statusPublished - Oct 20 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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