Constructing a self-assembling C3-symmetric covalently linked (fused) donor-acceptor-type molecule containing a hexaazatriphenylene core

A C-3-symmetric covalently linked (fused) molecule, HAT-IPN, comprising a 13 fused ring system was synthesized by a condensation-cyclisation reaction between hexaazatriphenylenehexacarboxylic acid trisanhydride and 4,5-diamino-1,2-dioctyloxybenzene. This fused system exhibits ambipolar behaviour due to an n-type HAT-core at the center and three outer p-type fused dialkoxybenzimidazole moieties, which is confirmed by cyclic voltammetry. The self-assembling nature of this disc-shaped donor-acceptor type system is evident in C-13 NMR spectroscopy, dynamic light scattering studies, differential scanning calorimetry and atomic force microscopy (AFM) images, which illustrate the formation of the one-dimensional aggregates both in solution and in the film state; indicating its potential as an active component in organic electronic devices.