Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 43, Pages 13938-13944Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404028
Keywords
dicarboxylic acids; fluorescence; molecular recognition; nonlinear response; self-assembly
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Funding
- [25810051]
- Grants-in-Aid for Scientific Research [25810051] Funding Source: KAKEN
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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.
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