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1,2,5?Triphenylpyrrole derivatives with dual intense photoluminescence in both solution and solid state and their solvatochromism, polymorphic luminescent property

Five organic luminophores 1,2,5?triphenylpyrrole (TPP) derivatives 3a?e containing electron?withdrawing or electron?donating groups were synthesized by Pd?catalyzed Suzuki coupling of 1?phenyl?2,5?di(4'?bromophenyl) pyrrole and para?substituted phenylboronic acid. They possess good thermal stabilities with high decomposition temperatures above 310 °C. The investigation on the photophysical properties of the luminogens 3a?e indicated that they exhibited dual intense photoluminescence in both solution and solid state due to their twisted conformations, and their fluorescence quantum yields (?F) were 68.7%~94.9% in THF solution and 19.1%~52.0% in solid powder state. The compounds 3a?c with electron?acceptor exhibited remarkable solvatochromism with large Stokes shift attributing to their D???A structure and intramolecular charge transfer effect, especially, 3a with aldehyde group displays obvious red?shift of emission band from 445 nm to 564 nm as increasing solvent polarity. However, no obvious solvatochromic behavior was observed for compounds 3d?e containing electron?donating groups. Moreover, the luminophore 3a exhibited polymorphic luminescent property and crystallization?induced emission enhancement feature.

» Author: Junge Zhi, Yuanyuan Li, Yunxiang Lei, Lichao Dong, Longlong Zhang, Jianbing Shi, Bin Tong, Yuping Dong

» Reference: doi:10.1002/chem.201804074

» Publication Date: 24/10/2018

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