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

Peter Ribar; Tomáš Šolomek; Michal Juríček

doi:10.1021/acs.orglett.9b02683

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

Org Lett. 2019 Sep 6;21(17):7124-7128. doi: 10.1021/acs.orglett.9b02683. Epub 2019 Aug 15.

Authors

Peter Ribar¹, Tomáš Šolomek¹, Michal Juríček^{1

2}

Affiliations

¹ Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
² Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.

Abstract

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 ExBox⁴⁺ 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.