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Updated: Apr 24, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Benzo[1,2-b:3,4-b':5,6-b″]trithieno[3,2-b:6,5-b':9,8-b″]trithiophene: A Thiophene-Rich 3-Fold Symmetric Building
Prasanta Pal1,2, Kirill Bulgarevich1, Kazuo Takimiya1,2,3
1RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Abstract:
A straightforward three-step synthesis of a thiophene-rich 3-fold symmetric core structure, benzo[1,2-b:3,4-b':5,6-b″]trithieno[3,2-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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