Crafting diverse tetraphenylthiophene designs through comprehensive ‘classical’ Suzuki-Miyaura synthesis and electrochemical exploration

Abstract

We present a successful programmed synthesis of diverse designs of tetraphenylthiophene derivatives (TPTs, 16 out of 24 probable structures) and the intermediate triphenylthiophene derivatives (12 out of 20 probable structures) using optimized ‘classical’ Suzuki-Miyaura cross-coupling conditions through multiple routes starting from a single precursor, tetrabromothiophene. Our first-ever electrochemical analysis of various TPT-designs highlights the crucial influence of the arrangement of electronically distinct aryl units on the oxidation potentials of the TPTs. These findings provide insight on the TPT design-redox trend that may guide selective oxidative C–C coupling in TPTs for achieving π-expanded thiophenes.