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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
syn/anti-Oligothienoacene Diimides with up to 10 Fused Rings
Jingjing Wen1, Fei Qiu1, Han Liu1
1Beijing Advanced Innovation Center for Soft Matter Science and Engineering, State Key Lab of Organic-Inorganic Composites, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing, 100029, China.
Abstract:
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 π-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 cm2 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.
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