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Effect of Structure and Conformation on Fluorescence Properties in Novel Coumarin‐based Mannich Base Dyes
Author(s) -
Ni Xiaobo,
Guo Yuan,
Bu Huaiyu,
An Jing,
En Da
Publication year - 2012
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201200010
Subject(s) - chemistry , aniline , fluorescence , coumarin , titration , mannich base , mannich reaction , proton nmr , nitrogen atom , photochemistry , schiff base , elemental analysis , ring (chemistry) , organic chemistry , crystallography , physics , catalysis , quantum mechanics
Twelve novel coumarin‐based Mannich base dyes have been synthesized via introducing functional aminomethyl group at the 8 position of coumarin ring by Mannich reaction and their chemical structures were confirmed by IR, 1 H NMR, MS and elemental analysis. Moreover, the fluorescence intensities and relative quantum yields of all the dyes were measured and studied. The results illustrated that the heavy atom effect was obvious in our designed system and there was a relationship between the structures, the conformations and the fluorescence spectra of the coumarins. Meanwhile, the present β‐CD titration experiment illustrated that the aniline nitrogen atom was closely related to the photoinduced electron transfer (PET) course and the PET course was carried out via a conformational control mechanism.