Facile Synthesis of Nitrogen-Doped [(6.)m8]nCyclacene Carbon Nanobelts by a One-Pot Self-Condensation Reaction

Synthesis of fully conjugated carbon nanobelts (CNBs) remains one of the biggest challenges in organic chemistry. Herein, we report a facile synthesis of four nitrogen-doped [(6.)(m)8](n)cyclacene CNBs (m = 1-3; n = 3,4) with different sizes by a one-pot self-condensation reaction of three bis(o-aminobenzophenone) precursors. The belt-shaped structure was confirmed by Xray crystallographic analysis. The existence of eight-membered [1,5]diazocine rings releases the strain while maintaining weak pi-conjugation throughout the belt backbone, which is supported by electronic absorption spectra and frontier molecular orbital analysis. NMR measurements and magnetic shielding calculations suggest an alternating aromatic-nonaromatic ring structure, with a slightly more shielded chemical environment in the cavity. Our method opens the opportunities to access more sophisticated pconjugated 2D/3D belt-/cage-like molecules in a simple way.

Automated summary

A facile synthesis method for nitrogen-doped carbon nanobelts was reported, in which eight-membered rings release strain while maintaining weak pi-conjugation. The method opens opportunities to access more sophisticated p-conjugated 2D/3D belt-/cage-like molecules in a simple way.