Effect of Substituent Position on the Photophysical Properties of Triphenylpyrrole Isomers
2017
Dong, Lichao | Shang, Guojun | Shi, Jianbing | Zhi, Junge | Tong, Bin | Dong, Yuping
The charge distribution, molecular structure, and morphological packing significantly affect the photophysical properties of organic photoluminescent materials. In this work, two triphenylpyrrole isomers, 1,2,5- (TPP1) and 1,3,4- (TPP2), were first synthesized and characterized. Because of their different substituent positions, TPP1 possesses aggregation-caused emission quenching (ACQ) behavior while TPP2 exhibits aggregation-induced emission (AIE). Their different photoluminescent properties were systematically investigated by using UV–vis absorption spectroscopy, fluorescence spectroscopy, density functional theory (DFT) calculations, and single-crystal structure analysis. The results indicate that substituent position of the two phenyl groups predominately affects the charge distribution of the isomers and determines their molecular packing structures, which further cause the different restriction of intramolecular rotation (RIR) capabilities of phenyl rings, thus resulting in different luminescence properties of these two triphenylpyrrole isomers under different aggregate states.
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