Three-Fold Scholl-Type Cycloheptatriene Ring Formation around a Tribenzotriquinacene Core: Toward Warped Graphenes

Ho-Wang Ip; Chun-Fai Ng; Hak-Fun Chow; Dietmar Kuck

doi:10.1021/jacs.6b05820

Three-Fold Scholl-Type Cycloheptatriene Ring Formation around a Tribenzotriquinacene Core: Toward Warped Graphenes

J Am Chem Soc. 2016 Oct 26;138(42):13778-13781. doi: 10.1021/jacs.6b05820. Epub 2016 Aug 3.

Authors

Ho-Wang Ip¹, Chun-Fai Ng¹, Hak-Fun Chow¹, Dietmar Kuck²

Affiliations

¹ Department of Chemistry, Institute of Molecular Functional Materials, and The Center of Novel Functional Molecules, The Chinese University of Hong Kong , Shatin, Hong Kong.
² Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University , 33615 Bielefeld, Germany.

PMID: 27478989
DOI: 10.1021/jacs.6b05820

Abstract

A nonplanar polycyclic aromatic compound 6 bearing a tribenzotriquinacene (TBTQ) core merged with an o,p,o,p,o,p-hexaphenylene belt was prepared and characterized by NMR spectroscopy and X-ray crystallography. The key synthesis step involves three Scholl-type cycloheptatriene ring formation steps of the 1,4,8-tris(3',4'-dimethoxyphenyl)-TBTQ derivative 5. The bridging of each of the three TBTQ bays by 1,2-phenylene units in compound 6 gives rise to an unusual wizard hat shaped structure, which represents a promising key intermediate for the construction of nonplanar nanographene molecules bearing a TBTQ core.