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Regio- and stereo-selective [4+4] photodimerization of angular-shaped dialkyltetracenedithiophene

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Abstract

Angular-shaped dialkyltetracenedithiophenes (aTDTs) undergo [4+4] photodimerization in solution to form a butterfly-shaped skeleton. This reaction proceeds in a regio- and stereo-selective manner, forming only a single planosymmetric syn-[2,2]-daTDT out of six possible products. The photocycloaddition of aTDTs can take place topochemically in the thin-film state while maintaining regio- and stereo-selectivity. Stronger aliphatic dispersion forces and π–π interactions play important roles in forming the eclipsed dimeric complex that leads to the syn-[2,2]-daTDT isomer.

Graphical abstract: Regio- and stereo-selective [4+4] photodimerization of angular-shaped dialkyltetracenedithiophene

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Publication details

The article was received on 29 Nov 2018, accepted on 30 Nov 2018 and first published on 30 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC09485C
Citation: Chem. Commun., 2019, Advance Article
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    Regio- and stereo-selective [4+4] photodimerization of angular-shaped dialkyltetracenedithiophene

    T. Hsu, H. Chou, M. Liang, Y. Lai and Y. Cheng, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09485C

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