Catalyst-free 2+2 Photodimerization of 1,4-Bis[2-(4-pyridyl)ethenyl]-benzene in Solution Under Low Power UV Irradiation

doi:10.1007/s40242-020-9116-3

Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (5): 816-820.doi: 10.1007/s40242-020-9116-3

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Catalyst-free 2+2 Photodimerization of 1,4-Bis[2-(4-pyridyl)ethenyl]-benzene in Solution Under Low Power UV Irradiation

CHU Ning, XU Shuping, XU Weiqing

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, P. R. China

Received:2019-12-30 Revised:2020-04-02 Online:2020-10-01 Published:2020-10-01
Contact: XU Weiqing E-mail:wqxu@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos. 21873039, 21573087, 21573092).

Abstract

Abstract: Two different kinds of configurations of 1,4-bis[2-(4-pyridyl)ethenyl]-benzene(trans-bpeb and cis-bpeb) were achieved, and a bpeb dimer was synthesized in dimethyl sulfoxide(DMSO). Compared with the previous work that synthesized the bpeb dimer or polymer in crystal with a template agent needed, the reaction occurred in a solution phase in the present method. A hand-held ultraviolet lamp(365 nm) with the power of 12 W and the Watt density of 0.35 mW/cm² can realize the photodimerization of bpeb, instead of the high-power mercury lamp in most previous studies. Unlike other 2+2 cycloaddition in liquid state using catalysts even noble metals, no catalysts were required here, which is cost-saving. Only the trans-pbeb can start the cycloaddition and the formation of the close J-aggregations of trans-pbeb in DMSO is a precondition for explaining the 2+2 photodimerization. The productivity for the 2+2 cycloaddition product was achieved as 55.6%.

Key words: 2+2 Photodimerization, 1,4-Bis[2-(4-pyridyl)ethenyl]-benzene, Catalyst-free

CHU Ning, XU Shuping, XU Weiqing. Catalyst-free 2+2 Photodimerization of 1,4-Bis[2-(4-pyridyl)ethenyl]-benzene in Solution Under Low Power UV Irradiation[J]. Chemical Research in Chinese Universities, 2020, 36(5): 816-820.

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Catalyst-free 2+2 Photodimerization of 1,4-Bis[2-(4-pyridyl)ethenyl]-benzene in Solution Under Low Power UV Irradiation

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