Effects of π-Extended Aromatic Fragments on Tris(hexa-<i>peri</i>-hexabenzocoronenyl)methyl Radical and Cation: Synthesis, Radical Transformation, and Reactivity Insights
Xin Sun, Xu‐Lang Chen, Jinku Bai, Dan‐Yang Wang, Jiaqi Liang, Junfeng Xiang, Xiang Hao, Tongling Liang, Aijiao Guan, Qian Li, Han‐Yuan Gong
Abstract
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 SnCl 2 -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.
Topics & Concepts
ChemistryHEXAReactivity (psychology)TrisPeriRadical ionMedicinal chemistryTransformation (genetics)PhotochemistryStereochemistryOrganic chemistryIonMedicineBiochemistryPhilosophyTheologyAlternative medicinePathologyGeneSynthesis and Properties of Aromatic CompoundsOrganic Light-Emitting Diodes ResearchLuminescence and Fluorescent Materials