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

Tze Gang Hsu, Hsiao Chieh Chou, Ming Ju Liang, Yu Ying Lai*, Yen-Ju Cheng

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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.

Original languageEnglish
Pages (from-to)381-384
Number of pages4
JournalChemical Communications
Volume55
Issue number3
DOIs
StatePublished - 1 Jan 2019

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