Stepwise Cyanation of Naphthalene Diimide for n-Channel Field-Effect Transistors

Stepwise cyanation of tetrabromonaphthalenediimide (NDI) 1 gave a series of cyanated NDIs 2–5 with the monocyanated NDI 2 and dicyanated NDI 3 isolated. The tri- and tetracyano- NDIs 4 and 5 show intrinsic instability toward moisture because of their extremely low-lying LUMO energy levels. The partially cyanated intermediates can be utilized as air-stable n-type semiconductors with OFET electron mobility up to 0.05 cm2 V–1 s–1.以四溴萘二酰亚胺（NDI）1为起始底物，通过分步氰化反应合成了一系列氰基化NDI产物2~5，其中成功分离得到单氰基化NDI 2与二氰基化NDI 3。三氰基化NDI 4与四氰基化NDI 5因拥有极低的最低未占据分子轨道（LUMO）能级，对水分表现出固有不稳定性。部分氰基化的中间体可用作空气稳定的n型半导体，其有机场效应晶体管（Organic Field-Effect Transistor, OFET）电子迁移率最高可达0.05 cm² V⁻¹ s⁻¹。