Zigzag‐Elongated Fused π‐Electronic Core: A Molecular Design Strategy to Maximize Charge‐Carrier Mobility. Issue 1 (15th November 2017)

• Record Type: Journal Article
• Authors: Yamamoto, Akito; Murata, Yoshinori; Mitsui, Chikahiko; Ishii, Hiroyuki; Yamagishi, Masakazu; Yano, Masafumi; Sato, Hiroyasu; Yamano, Akihito; Takeya, Jun; Okamoto, Toshihiro
• Is Part Of: Advanced science. Volume 5:Issue 1(2018)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2017-11-15
• Subjects: high carrier mobility -- highly stabilized crystal phase -- molecular orbital configuration -- organic semiconductor -- zigzag‐shaped π‐electronic core; Science -- Periodicals; 505
• DOI: 10.1002/advs.201700317
• Languages: English
• ISSNs: 2198-3844

Abstract

Abstract: Printed and flexible electronics requires solution‐processable organic semiconductors with a carrier mobility (μ) of ≈10 cm 2 V −1 s −1 as well as high chemical and thermal durability. In this study, chryseno[2, 1‐ b :8, 7‐ b ′]dithiophene (ChDT) and its derivatives, which have a zigzag‐elongated fused π‐electronic core (π‐core) and a peculiar highest occupied molecular orbital (HOMO) configuration, are reported as materials with conceptually new semiconducting π‐cores. ChDT and its derivatives are prepared by a versatile synthetic procedure. A comprehensive investigation reveals that the ChDT π‐core exhibits increasing structural stability in the bulk crystal phase, and that it is unaffected by a variation of the transfer integral, induced by the perpetual molecular motion of organic materials owing to the combination of its molecular shape and its particular HOMO configuration. Notably, ChDT derivatives exhibit excellent chemical and thermal stability, high charge‐carrier mobility under ambient conditions (μ ≤ 10 cm 2 V −1 s −1 ), and a crystal phase that is highly stable, even at temperatures above 250 °C. Abstract : Chryseno[2, 1‐ b :8, 7‐ b ′]dithiophene (ChDT) derivatives, which have a peculiar highest occupied molecular orbital (HOMO) configuration are newly designed and developed. This HOMO configuration is insusceptible to the change rate of the transfer integral from the molecular displacement in an aggregated structure induced by molecular motion. Notably, the synthesizedChDT derivatives exhibit a high mobility up to 10 cm 2 V −1 s −1 .