Regio- and Chemo-selective C-H Arylation of 3-Bromothiophene: A Synthesis Shortcut to Versatile π-Conjugated Building
Min-Ling Cao1, Kun-Mu Lee2,3, Xiao-Wei Wu1
1Department of Chemical and Materials Engineering, National Central University, Jhongli District, Taoyuan City, 320, Taiwan.
Abstract:
Unlike traditional multi-step synthetic approaches, we developed a single-step synthesis of versatile π-conjugated building blocks bearing post-functionalizable C-H and C-Br bonds. Direct C-H arylation of 3-bromothiophene with various iodo(hetero)aryls was successfully carried out with good regio- and chemo-selectivity. Under optimized reaction conditions, 20 new compounds were facilely prepared in yields up to 91 %. One of the obtained compounds was demonstrated to further extend its conjugation length using a succinct synthetic plan to create two symmetrical oligo(hetero)aryls (MLC01 and MLC02) that were fabricated as effective hole-transporting materials (HTM) for perovskite solar cells (PSC). PSC devices utilizing MLC01 as hole-transport layer displayed promising power conversion efficiencies of up to 17.01 %.
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