Synthesis and Properties of Novel Borondipyrromethene (BODIPY)-Tethered Triphenylamine Conjugates
Yucai Wang A B , Junxu Liao B C , Bangying Wang A B , Hongbiao Chen A C , Hongbin Zhao B , Min Peng B and Sujuan Fan BA College of Chemistry, Xiangtan University, Hunan 411105, China.
B College of Chemistry and Environmental Engineering, Dongguan University of Technology, Guangdong 523808, China.
C Corresponding authors. Email: liaojunxu503@sina.com; zhaohbhanlf@163.com
Australian Journal of Chemistry 68(10) 1485-1491 https://doi.org/10.1071/CH15026
Submitted: 28 January 2015 Accepted: 12 March 2015 Published: 22 April 2015
Abstract
A series of novel donor–acceptor type borondipyrromethene (BODIPY)-tethered triphenylamine conjugates (BDP4–8) containing one or two BODIPY cores attached to a triphenylamine scaffold at the 4- or 4,4′- positions were successfully synthesised via a mild and effective protocol. Their photophysical and electrochemical properties were investigated. The absorption spectra indicated that the meso-substituted BODIPY with triphenylamine did not give rise to an intense intramolecular charge transfer (ICT) and did not effectively extend the conjugated length compared with substitution at the 2,6- and 3,5-positions as previously reported. It is worth noticing that the asymmetric mono-BODIPY-tethered triphenylamine conjugates (BDP5, BDP7) showed an electronic distribution imbalance due to the special 3D propeller shape of triphenylamine resulting in twisted molecular space configurations. In contrast, the symmetric bis-BODIPY-tethered triphenylamine conjugates (BDP4, BDP6, and BDP8) exhibited a balanced electronic distribution. The photoluminescence spectra of these conjugates exhibited significant Stokes shifts (5300–6700 cm–1), which caused fluorescence emission spectra in near-infrared regions. Cyclic voltammograms reveal that the asymmetric mono-BODIPY-tethered triphenylamine conjugates (BDP5, BDP7) have higher LUMO energy levels and lower HOMO energy levels, thus resulting in larger bandgaps than the bis-BODIPY-tethered triphenylamine ones.
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