syn/anti-Oligothienoacene Diimides with up to 10 Fused Rings

We report a facile and powerful strategy to prepare libraries of oligothienoacene diimides that include anti- and syn-isomers using palladium-catalyzed C-H activation and an unexpected 1,2-sulfur migration. Through this strategy, a series of oligothienoacene diimides containing 6, 8, and 10 fused rings were synthesized. The molecular geometry and extent of pi-conjugation have dramatic effects on the electronic properties, degree of crystallinity, and charge-carrier transport properties. Notably, single-crystal microfibers of syn-3 c show electron mobilities up to 4.2 cm(2) V-1 s(-1), illustrating the significant potential of these materials for organic electronic devices. Our work demonstrates the versatility of this strategy for the development of oligothienoacene diimide libraries, in particular complex and large syn-oligothienoacene diimides, which are difficult to prepare by present methods.

Automated summary

A facile strategy involving palladium-catalyzed C-H activation and unexpected 1,2-sulfur migration was used to prepare libraries of oligothienoacene diimides with anti- and syn-isomers, leading to the synthesis of series of oligothienoacene diimides with 6, 8, and 10 fused rings. These materials showed significant potential for organic electronic devices, with the syn-isomer demonstrating electron mobilities up to 4.2 cm(2) V-1 s(-1) in single-crystal microfibers.