What question did this study set out to answer?

The aim is to synthesize a thiophene-rich core structure and analyze the effect of modifications on its properties.

April 25, 2026Organic Letters0 citationsOpen Access

Benzo1,2- b :3,4-b′:5,6- b ″trithieno3,2- b :6,5- b ′:9,8- b ″trithiophene: A Thiophene-Rich 3-Fold Symmetric Building Block for π-Extended Materials

PPPrasanta PalTohoku University KBKirill BulgarevichRIKEN Center for Emergent Matter Science KTKazuo Takimiya

Key Points

The aim is to synthesize a thiophene-rich core structure and analyze the effect of modifications on its properties.
Developed a three-step synthesis for benzo[1,2-b:3,4-b′:5,6-b″]trithieno.
Utilized iridium-catalyzed borylation and Suzuki-Miyaura cross-coupling to modify thiophene rings.
Conducted sulfonation of inner thiophene rings using m-chloroperoxybenzoic acid.
Synthesized BTTT core successfully with triaryl derivatives created through modifications.
Demonstrated how π-extension affects the electronic structure of BTTT.
Identified that sulfonation can selectively tune the electronic properties of the core.

Abstract

A straightforward three-step synthesis of a thiophene-rich 3-fold symmetric core structure, benzo1,2-b:3,4-b':5,6-b″trithieno3,2-b:6,5-b':9,8-b″trithiophene (BTTT), was developed. The α-positions of the outermost thiophene rings can be readily modified via iridium-catalyzed borylation followed by the Suzuki-Miyaura cross-coupling reaction or the direct arylation reaction with aryl bromides, leading to triaryl derivatives. Furthermore, the sulfur atoms in the inner thiophene rings can be selectively sulfonated via oxidation with m-chloroperoxybenzoic acid, thereby tuning the electronic structure of the BTTT core. The structural and electronic properties of the parent BTTT and its derivatives were elucidated to reveal the effects of π-extension and sulfonation.

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