title: Asymmetric Alkylthienyl Thienoacenes Derived from Anthra[2,3-b]thieno[2,3-d]thiophene for Solution-Processable Organic Semiconductors.
abstract: Anthra[2,3-b]thieno[2,3-d]thiophene (ATT), which is readily accessed from thieno[3,2-b]thiophene and 2,3-naphthalenedicarboxylic anhydride, allows for selective substitution at the terminal thiophene ring, thereby providing asymmetric monoalkyl and monoalkylthienyl thienoacenes. Alkyl-substituted ATT (CnATT, n = 6, 8, 10, 12) has characteristics of a p-type field-effect transistor (FET), with mobility on the order of 0.01 cm2V-1s-1, which is the same as ATT. Conversely, alkylthienyl-substituted ATT (CnTATT, n = 6, 8, 10, 12) exhibits FET mobility of 0.15-1.9 cm2V-1s-1, which is up to 2 orders of magnitude greater than that of ATT and CnATT. Moreover, CnTATT forms crystalline thin films both by spin coating and drop casting, and C8TATT in particular exhibits a mobility of up to 1.6 cm2V-1s-1in the drop-cast film. X-ray diffraction patterns of CnTATT thin films indicate that the molecules become oriented edge-on at the substrate surface with a highly ordered structure in the in-plane direction. Accordingly, CnTATT serves as a solution-processable p-type organic field-effect transistor, where the additional thiophene ring contributes significantly to the highly ordered thin-film structure and the high carrier mobility.
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Ogawa
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Yamamoto
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Chiyo
authors.initials: C
authors.lastname: Miura
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Shigeki
authors.initials: S
authors.lastname: Tamura
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Mitsuki
authors.initials: M
authors.lastname: Saito
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Mamada
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Kumaki
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Shizuo
authors.initials: S
authors.lastname: Tokito
authors.affiliation: Graduate School of Science and Engineering, Yamagata University , 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Hiroshi
authors.identifier: http://orcid.org/0000-0003-4100-9995
authors.initials: H
authors.lastname: Katagiri
keywords: alkyl chain effect; asymmetric oligomer; high mobility; organic field-effect transistor; organic semiconductor; solution process; structure−property relationship; thienoacene