Quantum chemical study of electron structure and charge transport properties of symmetric acenequinones

Abstract A systematic theoretical study using density functional theory is presented to estimate the structural, electronic, and charge-transfer characteristics of a symmetric fluorination of acenequinones outer rings. The change in aromaticity of model derivatives was described by different types of aromaticity indices. By considering a hopping mechanism and using the Marcus theory in combination with the Einstein-Smoluchowski relation, electronic drift mobilities were predicted for selected dimer configurations obtained from X-ray structures of anthraquinone, 6,13-pentacenequinone and its octafluorinated derivatives. The analysis of obtained data showed that the fluorination of the outer rings of acenequinones can lower the energy of the lowest unoccupied molecular orbital to the range from −3.0 to −4.0 eV, i.e. typical for organic n-type semiconducting materials. Finally, potential electric semiconductivity of available X-ray structures relating to drift mobilities was discussed.