Effects of π-Extended Aromatic Fragments on Tris(hexa-peri-hexabenzocoronenyl)methyl Radical and Cation: Synthesis, Radical Transformation, and Reactivity Insights

Neutral organic radicals have attracted interest for their stability and redox activity. We synthesized π-extended triarylmethanol (1-OH) with three HBC units, which undergoes SnCl₂-mediated radical transformation into nanographenes. Protonation with trifluoroacetic acid forms a carbocation (1⁺) that rapidly reverts to 1-OH in air, reflecting the destabilizing effect of π extension. These findings reveal how extended aromatic frameworks influence radical and cation stability, offering guidance for the design of 3D nanographene-based materials.