TY - JOUR
T1 - Synthesis, spectral properties and photostability of novel boron-dipyrromethene dyes
AU - Cui, Aijun
AU - Peng, Xiaojun
AU - Fan, Jiangli
AU - Chen, Xiuying
AU - Wu, Yunkou
AU - Guo, Binchen
N1 - Funding Information:
This work was financially supported by the Education Ministry of China and the National Natural Science Foundation of China (project 20128005, 20376010 and 20472012).
Copyright:
Copyright 2007 Elsevier B.V., All rights reserved.
PY - 2007/2/5
Y1 - 2007/2/5
N2 - Two series of novel boron-dipyrromethene (BODIPY) dyes containing 8-phenyl groups have been synthesized and their spectral properties have been studied. Series 2 with four methyl groups at 1,3,5,7-positions show much higher fluorescence quantum yields and extinction coefficients than series 1 (without methyl groups). The "push-pull" electronic effect caused by the methyl groups at 3 and 5 positions is a significant positive factor to the high quantum yields of 2. The X-ray structure analysis of 1c and 2c reveals that steric expulsion exists between the phenyl and adjacent two methyl groups. Moreover, the steric expulsion might block the intramolecular vibronic relaxation and internal conversion of the excited 2, which also contributes to their high fluorescence quantum yields. The substituent effects on photostability and redox potentials of these dyes have been discussed.
AB - Two series of novel boron-dipyrromethene (BODIPY) dyes containing 8-phenyl groups have been synthesized and their spectral properties have been studied. Series 2 with four methyl groups at 1,3,5,7-positions show much higher fluorescence quantum yields and extinction coefficients than series 1 (without methyl groups). The "push-pull" electronic effect caused by the methyl groups at 3 and 5 positions is a significant positive factor to the high quantum yields of 2. The X-ray structure analysis of 1c and 2c reveals that steric expulsion exists between the phenyl and adjacent two methyl groups. Moreover, the steric expulsion might block the intramolecular vibronic relaxation and internal conversion of the excited 2, which also contributes to their high fluorescence quantum yields. The substituent effects on photostability and redox potentials of these dyes have been discussed.
KW - Boron-dipyrromethene dye
KW - Crystal structure
KW - Cyclovoltammetry
KW - Fluorescence quantum yield
KW - Internal conversion
KW - Intramolecular vibronic relaxation
KW - Photostability
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U2 - 10.1016/j.jphotochem.2006.07.015
DO - 10.1016/j.jphotochem.2006.07.015
M3 - Article
AN - SCOPUS:33846021270
SN - 1010-6030
VL - 186
SP - 85
EP - 92
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
IS - 1
ER -