<i>N</i>‑Alkyldinaphthocarbazoles, Azaheptacenes, for Solution-Processed Organic Field-Effect Transistors

Abstract

Substituted <i>N</i>-alkyldinaphthocarbazoles were synthesized using a key double Diels–Alder reaction. The angular nature of the dinaphthocarbazole system allows for increased stability of the conjugated system relative to linear analogues. The <i>N</i>-alkyldinaphthocarbazoles were characterized by UV–vis absorption and fluorescence spectroscopy as well as cyclic voltammetry. X-ray structure analysis based on synchrotron X-ray powder diffraction revealed that the <i>N</i>-dodecyl-substituted compound was oriented in an intimate herringbone packing motif, which allowed for p-type mobilities of 0.055 cm² V^–1 s^–1 from solution-processed organic field-effect transistors