Synthesis and Photophysical and Electrochemical Properties of Structural Isomers of Pyrazine-Based D-π-A-π-D Fluorescent Dyes

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<jats:title>Abstract</jats:title> <jats:p>The structural isomers of D-π-A-π-D fluorescent dyes 2,5-PD and 2,6-PD which are substituted with two diphenylamine-thienylcarbazole moieties (electron-donating and π-conjugated unit) on 2,5- and 2,6-positions of a pyrazine ring (electron-withdrawing unit) have been developed. It was found that the structural isomers 2,5-PD and 2,6-PD show a significant solvatofluorochromism (λem = 513–614 and 480–588 nm for 2,5-PD and 2,6-PD, respectively). The photophysical and electrochemical measurements, and density functional theory calculations reveal that 2,5-substituted pyrazine dye 2,5-PD possesses stronger photoabsorption and fluorescence properties in a longer wavelength region and at a lower LUMO energy level, compared to the 2,6-substituted structural isomer 2,6-PD.</jats:p>

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