title: Translation of dicarboxylate structural information to fluorometric optical signals through self-assembly of guanidinium-tethered oligophenylenevinylene.
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.
authors.affiliation: Institute for Advanced Study, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395 (Japan), Fax: (+81) 92-805-3814; Nanotechnology Laboratory, Institute of Systems, Information Technologies and Nanotechnologies (ISIT), 4-1 Kyudai-Shinmachi, Nishi-ku, Fukuoka 819-0388 (Japan). tnoguchi@mail.cstm.kyushu-u.ac.jp.
authors.forename: Takao
authors.initials: T
authors.lastname: Noguchi
authors.forename: Bappaditya
authors.initials: B
authors.lastname: Roy
authors.forename: Daisuke
authors.initials: D
authors.lastname: Yoshihara
authors.forename: Youichi
authors.initials: Y
authors.lastname: Tsuchiya
authors.forename: Tatsuhiro
authors.initials: T
authors.lastname: Yamamoto
authors.forename: Seiji
authors.initials: S
authors.lastname: Shinkai
keywords: dicarboxylic acids; fluorescence; molecular recognition; nonlinear response; self-assembly