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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 oligophenyle-nevinylene 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. [ABSTRACT FROM AUTHOR]

A novel tetraphenylethene-based fluorescence (FL) chemosensor exhibits nonlinear turn-on FL switching though cooperative binding of L-tartarate, where its convergent binding to form cyclic substructures is responsible for the FL increase. This binding scheme achieves selective detection of dicarboxylates over monocarboxylates, thus is potentially applicable to the preliminary screening for metabolic disorders. [ABSTRACT FROM AUTHOR]

Molecular Recognition Synergistic marriage of self‐assembly and fluorescence (FL) signaling has realized fluorometric readout of dicarboxylates. A newly developed guanidinium‐tethered oligophenylenevinylene (OPV‐G) exhibits characteristic self‐assembling behaviors toward L‐ and meso‐tartarate. Therein, the different self‐assembly modes termed J‐ and H‐type are directed to afford fibrous and finite aggregates, respectively. Such a difference derived from the inherent tartarate structures is eventually embodied as the unique FL responses. For more details, see the Full Paper by T. Noguchi, S. Shinkai et al. on page 13938 ff. [ABSTRACT FROM AUTHOR]