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Translation of Dicarboxylate Structural Information to Fluorometric Optical Signals through Self‐Assembly of Guanidinium‐Tethered Oligophenylenevinylene
Author(s) -
Noguchi Takao,
Roy Bappaditya,
Yoshihara Daisuke,
Tsuchiya Youichi,
Yamamoto Tatsuhiro,
Shinkai Seiji
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404028
Subject(s) - fluorescence , chemistry , translation (biology) , nanoscopic scale , crystallography , biophysics , biological system , nanotechnology , materials science , physics , biochemistry , biology , optics , messenger rna , gene
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 CC 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.