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JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, vol.28, no.7, pp.490-496, 2015 (SCI-Expanded, Scopus)
Parameterization scheme used in geometry-based aromaticity index Harmonic Oscillator Model for Heterocycles with p-electrons and n-electron delocalization was extended to cover certain pnictogen (group 15) and chalcogen (group 16) elements, for example, phosphorus, arsenic, selenium, and tellurium. Thus, assessment of aromaticities of dibenzofuran-like and carbazole-like molecular skeletons including the aforementioned pnictogens and chalcogens besides nitrogen, oxygen, and sulfur was made possible. Our results have shown that aromaticity of five-membered and six-membered rings in the considered skeletons can be independently treated from each other. Arsenic, phosphorus, and sulfur are the most suitable heteroatoms in the considered molecular skeletons to be used in designing pi-conjugated functional materials, because they have potentially smaller band gap due to the presence of the less aromatic flanking benzenes. Differences in aromaticities of two flanking benzenes of the molecular skeletons including pnictogens are more pronounced than those of molecular skeletons including chalcogens. Copyright (C) 2015 John Wiley & Sons, Ltd.