American Chemical Society
ol6b03819_si_002.cif (189.13 kB)

Dithieno-Fused Polycyclic Aromatic Hydrocarbon with a Pyracylene Moiety: Strong Antiaromatic Contribution to the Electronic Structure

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posted on 2017-01-30, 05:31 authored by Chaolumen, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata
A synthetic route to dithieno-fused CP-PAHs with a pyracylene segment is reported. A combination of experimental and theoretical studies revealed a strong contribution of antiaromatic character to the electronic structure of this dithieno-fused CP-PAH. Anisotropy of current-induced density (ACID) calculations indicated a significantly increased paramagnetic ring current on the two pentagonal rings, which is more prominent than that of the dibenzo-fused analogue. Furthermore, enhanced electron affinity and a consequently decreased HOMO–LUMO gap were observed for this dithieno-fused CP-PAH.