Gram-Scale Synthesis and Supramolecular Complex of Precursors of Clar's Hydrocarbon Triangulene.

Org Lett

Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.

Published: September 2019

We present to date the most efficient gram-scale synthesis of triangulene-4,8-dione and 12-hydroxytriangulene-4,8-dione, the precursors of Clar's hydrocarbon, in overall yields >50%. The direct dihydroprecursors of triangulene, obtained upon reduction of triangulene-4,8-dione, were stabilized in a supramolecular complex with a tetracationic cyclophane ExBox and characterized by single-crystal X-ray crystallography. This result represents the first step in an endeavor to stabilize the fragile core of triangulene in an inclusion complex in solution and solid state.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6737831PMC
http://dx.doi.org/10.1021/acs.orglett.9b02683DOI Listing

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