The Dual-State Luminescent Mechanism of 2,3,4,5-Tetraphenyl-1H-pyrrole

Chemistry : a European Journal
Yunxiang LeiYu-Ping Dong

Abstract

2,3,4,5-Tetraphenyl-1H-pyrrole (TePP) was synthesized by a simple one-step reaction. The compound showed a balanced emission in both the solution and solid state with the absolute quantum yield of ΦF/THF =65.6 % and ΦF/solid =74.3 %, respectively. Temperature and viscosity variation measurements demonstrated that the phenyl group at the 1-position (N-position) of the pyrrole core can act as a rotor in pyrrole-based molecules, which can consume the excited energy and reduce the molecular emission in solution. TePP without the phenyl group at the 1-position can effectively enhance the emission in solution. Single-crystal analysis showed that the phenyl groups at the 2,5-positions of pyrrole extend the molecular conjugation and lock the conformation. The phenyl groups at the 3,4-positions with a twisted conformation prevent their molecules from close packing and are helpful for aggregated emission. A delicate balance between the twisting conformation and rigid conjugation takes advantage of both ACQ and AIE luminogens. The strategy can tune the AIE, ACQ, or solution and solid dual-state emission properties of pyrrole-based molecules by simply altering the position of phenyl groups, which provides a great opportunity to explore the...Continue Reading

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Citations

Apr 2, 2019·Chemistry : a European Journal·Abdusalom A SuleymanovKay Severin
Jun 24, 2021·Chemical Communications : Chem Comm·Shinya Sugiura, Hiromitsu Maeda
Dec 3, 2020·The Journal of Organic Chemistry·Dan ChangGuo-Jun Deng
Sep 5, 2020·Journal of the American Chemical Society·Hang QuXiaoyu Cao
Jan 13, 2022·Nanoscale·Anyi ZhengPengfei Duan

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