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

J Am Chem Soc

Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany.

Published: October 2016

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.

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http://dx.doi.org/10.1021/jacs.6b05820DOI Listing

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