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

Chaolumen; Michihisa Murata; Atsushi Wakamiya; Yasujiro Murata

doi:10.1021/acs.orglett.6b03819

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

Org Lett. 2017 Feb 17;19(4):826-829. doi: 10.1021/acs.orglett.6b03819. Epub 2017 Jan 30.

Authors

Chaolumen¹, Michihisa Murata^{1

2}, Atsushi Wakamiya¹, Yasujiro Murata¹

Affiliations

¹ Institute for Chemical Research, Kyoto University , Uji, Kyoto 611-0011, Japan.
² PRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.

PMID: 28133961
DOI: 10.1021/acs.orglett.6b03819

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't