Synthesis and electronic properties of nitrogen-rich nanographene

Chem Commun (Camb). 2024 Jul 11;60(57):7343-7346. doi: 10.1039/d4cc01189a.

Abstract

A polycyclic aromatic hydrocarbon displaying twelve edge nitrogen centers for a 42 π-electron system is reported. This compound was synthesized via Sonogashira coupling of pyrimidine precursors, [2+2+2] cycloaddition of bis(aryl) alkynes, and anionic cyclodehydrogenation. Spectroscopy, electrochemistry, and computational results suggest a narrowing of the HOMO-LUMO gap compared to the N-free analogue. Metal coordination affects the optical properties of the extended π system.