Oxygen- and Sulfur-Bridged Bianthracene V-Shaped Organic Semiconductors

• Published in: Bulletin of the Chemical Society of Japan Vol. 90; no. 8; pp. 931 - 938
• Main Authors: Mitsui, Chikahiko, Yamagishi, Masakazu, Shikata, Ryoji, Ishii, Hiroyuki, Matsushita, Takeshi, Nakahara, Katsumasa, Yano, Masafumi, Sato, Hiroyasu, Yamano, Akihito, Takeya, Jun, Okamoto, Toshihiro
• Format: Journal Article
• Language: English
• Published: TOKYO The Chemical Society of Japan 2017; Chemical Soc Japan; Chemical Society of Japan
• Subjects: Charge transport; Chemistry; Chemistry, Multidisciplinary; Columnar structure; Crystal structure; Field effect transistors; Hole mobility; Mathematical analysis; Organic semiconductors; Oxygen; Physical Sciences; Science & Technology; Semiconductor devices; Single crystals; Sulfur; Transistors; HIGH-PERFORMANCE; PHYSICAL VAPOR GROWTH; STABILITY; CRYSTALS; HIGH-MOBILITY; DERIVATIVES; FIELD-EFFECT TRANSISTORS
• ISSN: 0009-2673; 1348-0634
• DOI: 10.1246/bcsj.20170030

A series of oxygen- and sulfur-bridged bianthracene V-shaped π-electronic cores are facilely synthesized. We clarify their fundamental properties and aggregated structures in single crystals as well as measure their transistor performances in single crystal field-effect transistors. Both V-shaped molecules possess bent structures induced by the intermolecular interaction in a herringbone-packing manner. A theoretical calculation study reveals that the driving force of the bent structures originates from the strong dispersion energy. Additionally, the bent conformation plays a crucial role in the formation of a dense packing structure, resulting in an attractive intermolecular overlap. An examination of the charge transport indicates that the hole mobility is up to 2.0 cm2/Vs. Finally, to understand the anisotropies of the mobility in single crystals, the transistors are evaluated when the channel direction is either parallel or orthogonal to the column direction in the herringbone packing along with their band structure calculations. Sulfur-bridged V-shaped π-electronic cores are more suitable for two-dimensional carrier-transport than oxygen-bridged analogs.