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Dipicolylamine styryldiazine derivatives: Synthesis and photophysical studies
Authors: Achelle Sylvain | Rodriguez-Lopez Julian | Bureš Filip | Robin-le Guen Francoise
Year: 2015
Type of publication: článek v odborném periodiku
Name of source: Dyes and Pigments
Publisher name: Elsevier Science
Place: Oxford
Page from-to: 305-311
Titles:
Language Name Abstract Keywords
cze Dipikolylamin-styryldiazinové deriváty:syntéza a fotofyzikální studia Byly syntetizovány nové D-pi-A push-pull molekuly nesoucí dipikolylamin jako donorní jednotku, diaziny jako akceptorní skupiny a styrenové fragmenty jako spojovací můstky. Všechny molekuly vykazují pi-pi* přenos v UV nebo Vis oblasti a fluorescenci žlutého světla při osvícení. Se vzrůstající polaritou rozpouštědla byl pozorován významný posun fluorescenčního maxima do „červené“ oblasti. V některých případech vede protonace k významným barevným změnám. Významný posun fluorescenčního spektra do „modré“ nebo „červené“ oblasti způsobuje také koordinace s ionty kovů Zn, Cd a Hg. diaziny;fluorescence;kationty kovů;intramolekulární přenos náboje;pi-konjugovaný systém;puch-pull molekuly
eng Dipicolylamine styryldiazine derivatives: Synthesis and photophysical studies Different D-pi-A push pull molecules in which dipicolylamine (DPA) is used as the donor group, different diazines as the acceptor groups, and styryl as the pi-conjugated spacer have been synthesized in a straightforward manner by aldol condensation of 4-(di-2-picolylamino)benzaldehyde and the appropriate methyldiazine. All of the compounds showed pi-pi* transitions in the UV or visible region and the emission of yellow-green light upon irradiation. Significant red shifts were observed in the fluorescence emission maxima of these compounds on increasing the solvent polarity, a finding that suggests the formation of an intramolecular charge-separated emitting state that is also supported by semi-empirical calculations. In some cases, protonation led to marked color changes, thus showing the ability of these molecules to function as colorimetric pH sensors. The DPA and diazine units can act as coordination sites for metal cations such as Zn2+, Cd2+ or Hg2+, leading to a blue or red shift in the fluorescence spectra due to the change in the intramolecular charge transfer properties. This phenomenon could become a powerful tool for the creation of multiple emission colors with a single molecule after suitable design. Diazines;Metal cations;Fluorescence;Intramolecular charge transfer;pi-conjugated systems;Push-pull molecules

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