The Regioselective Solid-State Photo-Mechanochemical Synthesis of Nanographenes with UV light

Abstract

Photochemical reactors inherently suffer from the low penetration depth of light and therefore rely on high dilutions to enable chemical reactions. Here we present the first method of UV (ultraviolet) photochemistry in the complete absence of bulk solvents in a ball mill. Triphenylene was synthesized by two routes, the Mallory reaction and the cyclodehydrochlorination (CDHC), resulting in yields of 81 and 92 %, respectively. The reaction was successfully scaled up to the gram scale and the robustness of the method was demonstrated for several different substrates. Finally, the regioselective assembly of nanographenes by mechanochemistry was demonstrated for larger systems. Thus, the mechanochemical approach presented here provides a powerful new tool for the atomically precise construction of nanographenes.