Synthesis of Dinaphtho[2,3- d :2',3'- d ']anthra[1,2- b :5,6- b ']dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties

• Published in: International journal of molecular sciences Vol. 21; no. 7; p. 2447
• Main Authors: Ishida, Takumi, Sawanaka, Yuta, Toyama, Ryota, Ji, Zhenfei, Mori, Hiroki, Nishihara, Yasushi
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01.04.2020; MDPI
• Subjects: Aromatic compounds; Atomic force microscopy; Chains; cycloaromatization; Energy; fastener effect; Field effect transistors; Negishi coupling reaction; organic field-effect transistor (OFET); p-type semiconductor; Semiconductor devices; Semiconductors; Spectrum analysis; Sulfur; thienoacene; Thin films; Transistors; X-ray scattering; organic field-effect transistor (OFET); fastener effect; Negishi coupling reaction; cycloaromatization; thienoacene; p-type semiconductor
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms21072447

To investigate organic field-effect transistor (OFET) properties, a new thienoacene-type molecule, 4,14-dihexyldinaphtho[2,3- :2',3'- ']anthra[1,2- :5,6- ']dithiophene (C6-DNADT), consisting of π-conjugated nine aromatic rings and two hexyl chains along the longitudinal molecular axis has been successfully synthesized by sequential reactions, including Negishi coupling, epoxidation, and cycloaromatization. The fabricated OFET using thin films of C6-DNADT exhibited p-channel FET properties with field-effect mobilities ( ) of up to 2.6 × 10 cm V s , which is ca. three times lower than that of the parent DNADT molecule (8.5 × 10 cm V s ). Although this result implies that the installation of relatively short alkyl chains into the DNADT core is not suitable for transistor application, the origins for the FET performance obtained in this work is fully discussed, based on theoretical calculations and solid-state structure of C6-DNADT by grazing incidence wide-angle X-ray scattering (GIWAXS) and atomic force microscopy (AFM) analyses. The results obtained in this study disclose the effect of alkyl chains introduced onto the molecule on transistor characteristics.