Intramolecular Locked Dithioalkylbithiophene‐Based Semiconductors for High‐Performance Organic Field‐Effect Transistors

• Published in: Advanced materials (Weinheim) Vol. 29; no. 35
• Main Authors: Vegiraju, Sureshraju, Chang, Bo‐Chin, Priyanka, Pragya, Huang, Deng‐Yi, Wu, Kuan‐Yi, Li, Long‐Huan, Chang, Wei‐Chieh, Lai, Yi‐Yo, Hong, Shao‐Huan, Yu, Bo‐Chun, Wang, Chien‐Lung, Chang, Wen‐Jung, Liu, Cheng‐Liang, Chen, Ming‐Chou, Facchetti, Antonio
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 01.09.2017
• Subjects: Charge transport; Chemical synthesis; Copolymerization; dithienothiophene; dithioalkylbithiophene; Field effect transistors; Grazing incidence; Locks; Molecular orbitals; organic field‐effect transistors; Organic semiconductors; Semiconductor devices; Single crystals; solution‐shearing; Transistors; dithienothiophene; solution-shearing; organic field-effect transistors; dithioalkylbithiophene
• ISSN: 0935-9648; 1521-4095
• DOI: 10.1002/adma.201702414

New 3,3′‐dithioalkyl‐2,2′‐bithiophene (SBT)‐based small molecular and polymeric semiconductors are synthesized by end‐capping or copolymerization with dithienothiophen‐2‐yl units. Single‐crystal, molecular orbital computations, and optical/electrochemical data indicate that the SBT core is completely planar, likely via S(alkyl)⋯S(thiophene) intramolecular locks. Therefore, compared to semiconductors based on the conventional 3,3′‐dialkyl‐2,2′‐bithiophene, the resulting SBT systems are planar (torsional angle <1°) and highly π‐conjugated. Charge transport is investigated for solution‐sheared films in field‐effect transistors demonstrating that SBT can enable good semiconducting materials with hole mobilities ranging from ≈0.03 to 1.7 cm2 V−1 s−1. Transport difference within this family is rationalized by film morphology, as accessed by grazing incidence X‐ray diffraction experiments. New 3,3′‐dithioalkyl‐2,2′‐bithiophene (SBT)‐based small‐molecular and polymeric semiconductors are synthesized by end‐capping or copolymerization with dithienothiophen‐2‐yl units. Charge transport is investigated for solution‐sheared films in field‐effect transistors demonstrating that SBT can enable good charge transport with hole mobilities ranging from ≈0.03 to 1.7 cm2 V−1 s−1.