Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors

H.-Y. Chen, G. Schweicher, M. Planells, S.M. Ryno, K. Broch, Andrew J. P. White, D. Simatos, M. Little, C. Jellett, S.J. Cryer, A. Marks, M. Hurhangee, J.-L. Brédas, H. Sirringhaus, I. McCulloch
Chem. Mater., 30 (21), pp. 7587-7592, (2018)

Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors

Keywords

Crystal Engineering, Organic Field-Effect Transistors

Abstract

​Three thiophene ring-terminated benzothieno[3,2-b]benzothiophene (BTBT) derivatives, C-C6-DBTTT, C-C12-DBTTT, and L-C12-DBTTT, were designed and synthesized, differing in the isomerization of alkyl chain position as well as aromatic core construction. A study of crystal structure and electronic properties combined with a theoretical investigation was performed to understand the structure–property relationships for the application of these molecules in organic field-effect transistors (OFETs). Different crystal packing structures were observed for these three isomers by single-crystal X-ray diffraction as a result of a crystal engineering molecular design approach. The highest charge-carrier mobility was observed for the isomer with a collinear core, L-C12-DBTTT. Preliminary results demonstrated a promising hole mobility of 2.44 cm2 V–1 s–1, despite the polymorphism observed in ambient conditions.

Code

DOI: 10.1021/acs.chemmater.8b02757

Sources

Website PDF

See all publications 2018