The excited state intramolecular charge transfer (ICT) reaction in a series of N, N-heterocyclic 4-aminobenzonitriles is investigated theoretically by a combination of density functional theory and multi-reference configuration interaction (DFT/MRCI). Experimentally, increasing ICT emission is observed with increasing ring size. Formation of both a planar and twisted ICT (PICT and TICT) state are energetically unfavorable in the small systems due to high inversion barriers. With increasing ring size, the TICT state is more stabilized than the]PICT state. A good agreement of the computed TICT state dipole moment is found with experimental values. The red-shifted fluorescence of all systems is explained by the TICT model due to both arguments.