Synthesis of porphyrin(2.1.2.1) with embedded naphthalene

Abstract

Expanded nonaromatic stable porphyrins(2.1.2.1) were successfully synthesized by 2,3-di(1H-pyrrol-2-yl)naphthalene as buliding blocks and aromatic aldehydes under acid catalyzed condensation conditions in acceptable isolated yields. NMR, X-ray diffraction analysis, absorption, electrochemical, and density functional theory revealed these macrocycles to be non-aromatic due to highly saddle-shaped molecular structures of dinaphthoporphyrin(2.1.2.1). The saddle-shaped dinaphthoporphyrins(2.1.2.1) with embedded naphthalene units as [Formula: see text]-conjugation units show perturbations to molecular structure, optical and electronic properties. The dinaphthoporphyrins(2.1.2.1) are effective macrocyclic ligands giving copper(II) and nickel(II) complexes.