N‑Alkyldinaphthocarbazoles, Azaheptacenes, for Solution-Processed Organic Field-Effect Transistors

Substituted N-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 N-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 N-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.