<i>N</i>‑Alkyldinaphthocarbazoles,
Azaheptacenes, for Solution-Processed Organic Field-Effect Transistors
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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 cm<sup>2</sup> V<sup>–1</sup> s<sup>–1</sup> from solution-processed organic field-effect transistors