Dinaphthothiepine Bisimide and Its Sulfoxide: Soluble Precursors for Perylene Bisimide,Journal of the American Chemical Society

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Dinaphthothiepine Bisimide and Its Sulfoxide: Soluble Precursors for Perylene Bisimide
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-06-16 , DOI: 10.1021/jacs.0c04096
Sakiho Hayakawa ₁ , Kyohei Matsuo ₂ , Hiroko Yamada ₂ , Norihito Fukui ₁ , Hiroshi Shinokubo ₁

Affiliation

The synthesis and properties of dinaphtho[1,8-bc:1',8'-ef]thiepine bisimide (DNTBI) and its oxides are described. Their molecular design is conceptually based on the insertion of a sulfur atom into the perylene bisimide (PBI) core. These sulfur-inserted PBI derivatives adopt nonplanar structures, which significantly increases their solubility in common organic solvents. Upon electron-injection, light-irradiation, or heating, DNTBI and its sulfoxides undergo sulfur-extrusion reactions to furnish PBI. The photo-induced and thermal sulfur extrusion reactions proceed almost quantitatively. This unique reactivity enabled the fabrication of a high-performance solution-processed n-type organic field-effect transistor with an electron mobility of up to 0.46 cm2 V-1 s-1.

中文翻译：

二萘硫平双酰亚胺及其亚砜：苝双酰亚胺的可溶性前体

描述了二萘并 [1,8-bc:1',8'-ef] 噻吩双酰亚胺 (DNTBI) 及其氧化物的合成和性质。他们的分子设计在概念上基于硫原子插入苝双酰亚胺 (PBI) 核。这些插入硫的 PBI 衍生物采用非平面结构，这显着增加了它们在常见有机溶剂中的溶解度。通过电子注入、光照射或加热，DNTBI 及其亚砜会发生硫挤出反应以提供 PBI。光诱导和热硫挤出反应几乎是定量进行的。这种独特的反应性使得能够制造出电子迁移率高达 0.46 cm2 V-1 s-1 的高性能溶液处理 n 型有机场效应晶体管。

更新日期：2020-06-16

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