Phenylenediamine-Linked, Folded Nanographene Dimers: Access to Structure-Dependent Redox Capability

• DOI: 10.1021/acs.joc.5c00145
• Publication Date: 2025-03-19T14:05:39Z
• Authors: Lan Ruan; Ranran Li; Meng Li; Yuxin Huang; Peng An

Polycyclic aromatic hydrocarbons (PAHs) with open-shell or redox characteristics are highly desirable due to their intriguing electronic properties and potential applications. Here, we demonstrate a series of phenylenediamine-linked nanographenes (NGs) 1–3 by connecting two aza-hexa-peri-hexabenzocoronene (HBC) units p-phenylene, p,p'-biphenylene, p,p"-terphenylene, respectively, unveil 3D conformations, structures, properties. As proved X-ray crystallographic analysis quantum chemical calculation, adopted anti-folded, Z-shaped structures rotatable single bonds. The structure-dependent capabilities were disclosed. For 1, stable monoradical cation was generated one-electron oxidation as the terminal product. revealed an unprecedented syn-folded structure 1+. However, 2 3 demonstrated redox-active molecules from neutral dication that each oxidative state can be precisely controlled oxidation/reduction.