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

Stepwise cyanation of tetrabromonaphthalenediimide (NDI) 1gave a series of cyanated NDIs 2–5with the monocyanated NDI 2and dicyanated NDI 3isolated. The tri- and tetracyano- NDIs 4and 5show 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 cm2V–1s–1. [ABSTRACT FROM AUTHOR]