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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).
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Finikova et al. (2003) studied this question.
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