Abstract
We present to date the most efficient gramscale 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 singlecrystal 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.