Novel route to functionalized tetraaryltetra[2,3]naphthaloporphyrins via oxidative aromatization.
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).
Finikova
Olga S
OS
Department of Biochemistry and Biophysics, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Cheprakov
Andrei V
AV
Carroll
Patrick J
PJ
Vinogradov
Sergei A
SA