Polarizability of polycyclic aromatic hydrocarbon compounds from the intermediate stages of the oxidative condensation of hexaphenylbenzene into hexa-peri-hexabenzocoronene

Benzenoid hydrocarbons have regular structures, attracting the opportunity to test the structural descriptors of their series. In the present study, we compared information entropy, Wiener indices, topological efficiencies, topological roundness, and symmetries of oligoacenes, phenacenes, and helicenes. We found and discussed the mismatches between the descriptors and the symmetry of benzenoids. Among the studied series, helicenes demonstrate the parity effect when the information entropy and topological roundness form saw-like functions depending on the number of the member, odd or even. According to our quantum chemical calculations, this parity effect has no consequences for such molecular properties as molecular polarizability and frontier molecular orbital energies. Further, we demonstrated that the changes in the structural descriptors upon the chemical reactions of benzenoids could be used for the numerical description of chemical processes. Interestingly, the view of the information entropy reaction profile is similar to the energy profiles of chemical reactions. Herewith, the intermediate chemical compounds have higher information entropy values compared with the initial and final compounds, which reminisce the activation barrier.

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Structural Descriptors of Benzenoid Hydrocarbons: A Mismatch between the Estimates and Parity Effects in Helicenes

Sabirov

Ori

Tukhbatullina

et al. 2022

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Polarizability of Kekulene, Septulene, and Nearest Non-Planar Polycyclic Aromatic Hydrocarbons

Lukmanov

Akhmetov

Sabirov

2022

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The polarizability of polycyclic aromatic hydrocarbons (PAHs) is an important property that relates to their abundance in natural environments. To assess the differences in the mean polarizability of planar and non-planar polycyclic aromatic hydrocarbons (PAHs), we computationally studied the PAH series of circulenes (kekulene C48H24, [13]circulene C52H26, and septulene C56H28), a number of the nearest helicenes, and their “expanded” isomers. We mean under “nearest” a close number of aromatic rings: 11 (C46H26), 12 (C50H28), 13 (C54H30), and 14 (C58H32). For these PAHs, we performed the quantum chemical calculations of thermodynamic and polarizability parameters with the PBE/3ζ density functional theory method, which is widely used in the theoretical chemistry of fullerenes and PAHs. The calculated mean polarizabilities (in Å3) ranged from 80.1 for [11]helicene to 135.5 for septulene, and while the circulenes and expanded helicenes had similar values, the mean polarizability of the normal helicenes was markedly lower. In all four pairs of helical PAHs, the expanded helicene was energetically considerably more favorable than its standard helicene isomer. Herewith, the ratio of their polarizabilities was equal to 1.3.

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Polarizability of polycyclic aromatic hydrocarbon compounds from the intermediate stages of the oxidative condensation of hexaphenylbenzene into hexa-peri-hexabenzocoronene

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Structural Descriptors of Benzenoid Hydrocarbons: A Mismatch between the Estimates and Parity Effects in Helicenes

Structural Descriptors of Benzenoid Hydrocarbons: A Mismatch between the Estimates and Parity Effects in Helicenes

Polarizability of Kekulene, Septulene, and Nearest Non-Planar Polycyclic Aromatic Hydrocarbons

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