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N-Triazinyl Derivatives of 1-and 9-aminoanthracene: Synthesis and Photo-Physical Properties
Authors: Přichystalová Hana | Almonasy Numan | Nepras Milos | Bureš Filip | Dvořák Miroslav | Michl Martin | Čermák Jiří | Burgert Ladislav
Year: 2013
Type of publication: článek v odborném periodiku
Name of source: Journal of Fluorescence
Publisher name: Springer
Page from-to: 425-437
Titles:
Language Name Abstract Keywords
cze N-Triazinyl deriváty 1-a 9-aminoanthracenu: syntéza a foto-fyzikální vlastnosti Nové N-triazinylové deriváty byly připraveny reakcí kyanurchloridu s 1- a 9-aminoanthracenenem a následnou nukleofilní substitucí chloru na triazinylovém kruhu methoxy a/nebo fenylamino skupinami. Sloučeniny byly charakterizovány H-1 a C-13 NMR a hmotnostními spektry. Byl studiván vliv chemické struktury a polarity rozpouštědla na UV/Vis absorpci a fluorescenci a a na fluorescenční kvantové výtěžky. Semiempirické výpočty prokázaly polární CT excitovaný singletový stav. N-Triazinyl deriváty; 1-aminoanthracen; 9-aminoanthracen; syntéza; foto-fyzikální vlastnosti
eng N-Triazinyl Derivatives of 1-and 9-aminoanthracene: Synthesis and Photo-Physical Properties New N-triazinyl derivatives were synthesized by reaction of cyanuric chloride with 1- and 9-aminoanthracenes and subsequent nucleophilic substitution of chlorine atoms on triazinyl ring with methoxy and/or phenylamino groups. The compounds were characterized by H-1 and C-13 NMR and mass spectra. The influence of the chemical structure and solvent polarity on the UV/Vis absorption and fluorescence spectra and fluorescence quantum yields were investigated. Semi-empirical computations revealed highly polar CT states in singlet excited state manifold connected with charge-transfer from the hydrocarbon moiety to the triazinyl ring. The relationships between the CT-to-emitting state energy gap, solvent polarity and fluorescence quantum yield were discussed. N-Triazinyl aminoanthracenes; synthesis; fluorescence spectra; quantum yield; quenching