Rules of Nucleophilic Additions to Zigzag Nanographene Diones**

Abstract

Nucleophilic addition of carbon-centered nucleophiles to nanographene ketones represents avaluable late-stage method for the functionalization of zigzag nanographenes,but its use is rare in the chemical literature.U sing two model systems,non-KekulØ triangulene-4,8-dione and KekulØ anthanthrone,w ei dentify unexpected regioselectivities and uncover the rules that govern these reactions.C onsidering the large number of nanographene ketones that have been reported since the pioneering work of Eric Clar,this method enables synthesis and exploration of hitherto unknown functionalizedn anographenes.

Subphthalocyanine–triangulene dyads: Property tuning for light‐harvesting device applications

“…Strong intermolecular interactions of the triangulene scaffold, as a result of mixing of the singly occupied molecular orbitals (SOMOs), 16 provide self-assembly ability of the triangular-shaped acceptor. As recently shown by Juríček et al, [17][18][19] triangulene-4,8-dione molecular motifs synthetically modified for further functionalization (Figure 1) can be obtained via robust synthetic routes on gram scale. In addition to exhibiting significantly higher solubility, these triangulene-4,8-diones are visible light/ near infrared emitters with large Stokes shifts and high quantum yields, while maintaining inherent triangulene redox properties.…”

Tethering Three Radical Cascades for Controlled Termination of Radical Alkyne peri-Annulations: Making Phenalenyl Ketones without Oxidants

“…, open-shell molecules) (Figure ). − For example, Anthony used this approach to prepare silylethynyl functionalized pentacenes while Arikawa and co-workers synthesized triangulene . Our group recently utilized polyaromatic diones to synthesize Kekulé and non-Kekulé diradicaloids with very low singlet/triplet gaps …”