Novel route to functionalized tetraaryltetra[2,3]naphthaloporphyrins via oxidative aromatization

Olga S Finikova; Andrei V Cheprakov; Patrick J Carroll; Sergei A Vinogradov

doi:10.1021/jo0347819

Novel route to functionalized tetraaryltetra[2,3]naphthaloporphyrins via oxidative aromatization

J Org Chem. 2003 Sep 19;68(19):7517-20. doi: 10.1021/jo0347819.

Authors

Olga S Finikova¹, Andrei V Cheprakov, Patrick J Carroll, Sergei A Vinogradov

Affiliation

¹ Department of Biochemistry and Biophysics, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.

PMID: 12968910
DOI: 10.1021/jo0347819

Abstract

A novel general route to substituted meso-tetraaryltetra[2,3]naphthaloporphyrins (Ar(4)TNP) and meso-tetraaryloctamethoxytetra[2,3]naphthaloporphyrins (Ar(4)(MeO)(8)TNP) via oxidative aromatization of nonaromatically fused porphyrin precursors is described. Ar(4)(MeO)(8)TNPs exhibit more red-shifted absorption bands than Ar(4)TNPs and differ dramatically in solubility. The first X-ray crystallographic structure of tetranaphthaloporphyrin, i.e., PdAr(4)TNP (Ar = 4-MeO(2)CC(6)H(4)), revealed that the degree of nonplanar distortion of this macrocycle is only slightly higher than that of the homologous tetrabenzoporphyrins (Ar(4)TBP).