Abstract
The dibenzo[d,d'']benzo[1,2-b:4,3-b']difuran skeleton exhibits a V-shape, which is highly desirable in semi-conductor applications. In this study, we synthesized V-shaped highly fused phthalonitrile derivatives and investigated the use of peripheral substituents to tune the crystal packing of the compounds. The palladium-mediated double C-H activation of 3,6-bis(aryloxy) phthalonitriles afforded 6,7dicyano-dibenzo[d,d'']benzo[1,2-b:4,3-b']difurans. The peripheral substituents affected the packing structure of the single crystals, particularly in the compounds with nBu groups, in which two-dimensional (2D) layered structures were observed. The peripheral substituents also affected the optical properties in the solution, film, and powder states. The layered structure suggested an improvement in the mobilities of organic semiconductors.(C) 2022 Elsevier Ltd. All rights reserved.
NSTL
Elsevier