Herein, we describe the design and synthesis of a suite of molecules based on a benzodithiophene “universal crystal engineering core”. After computationally screening derivatives, a trialkylsilylethyne-based crystal engineering strategy was employed to tailor the crystal packing for use as the active material in an organic field-effect transistor. Electronic structure calculations were undertaken to reveal derivatives that exhibit exceptional potential for high-efficiency hole transport. The promising theoretical properties are reflected in the preliminary device results, with the computationally optimized material showing simple solution processing, enhanced stability, and a maximum hole mobility of 1.6 cm2 V−1 s−1.
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The work was supported by the National Science Foundation Designing Materials to Revolutionize and Engineer our Future (NSF DMREF) program under Awards 1627428 (UKY), 1627453 (Princeton) and 1627925 (WFU). Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the University of Kentucky Information Technology Department and Center for Computational Sciences (CCS). Crystallography was supported by NSF-MRI awards CHE-0319176 and CHE-1625732.
All publication charges for this article have been paid for by the Royal Society of Chemistry.
Electronic supplementary information (ESI) available: Synthetic details, characterization of synthesized materials, absorption spectra, and additional information on computational details and device fabrication. CCDC 1833615–1833619 and 1922871–1922873. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc02930c
The supplementary files are also available for download as the additional files listed at the end of this record.
Petty, Anthony J. II; Ai, Qianxiang; Sorli, Jeni C.; Haneef, Hamna F.; Purdum, Geoffrey E.; Boehm, Alex M.; Granger, Devin B.; Gu, Kaichen; Rubinger, Carla Patricia Lacerda; Parkin, Sean R.; Graham, Kenneth R.; Jurchescu, Oana D.; Loo, Yueh-Lin; Risko, Chad; and Anthony, John E., "Computationally Aided Design of a High-Performance Organic Semiconductor: The Development of a Universal Crystal Engineering Core" (2019). Chemistry Faculty Publications. 176.