Issue 0, 1979

Synthesis of tetraphenylporphyrin molecules containing heteroatoms other than nitrogen. Part 4. Symmetrically and unsymmetrically substituted tetra phenyl-21,23-dithiaporphyrins

Abstract

The synthesis of symmetrically as well as unsymmetrically substituted tetraphenyl-21,23-dithiaporphyrins (S2TPP) is described. The reaction of 2,5-dilithiothiophen with substituted benzaldehydes is used for the preparation of substituted 2,5-bis(phenyihydroxymethyl)thiophens. Symmetrically substituted S2TPP molecules result from reaction of these dialcohols with equimolar quantities of pyrrole. Unsymmetrically substituted S2TPP molecules are obtained by first reacting one diol with an excess of pyrrole and subsequently reacting the intermediate obtained with another diol. The compounds prepared are the tetrakis-(p-methoxyphenyl)-, tetrakis-(p-chlorophenyl)-, tetrakis-(p-fluorophenyl), α,β-bis-(p-methoxyphenyl)-γ,δ-diphenyl-,α,β-bis-(p-fluorophenyl)-γ,δ, diphenyl-,α,β-bis-(p-chlorophenyl)-γ,δ-bis-(p-methoxyphenyl)-, and αβ,-bis-(p-fluorophenyl)-γ,δ-bis-(p-methoxyphenyl)-porphyrins. The optical and 1H n.m.r. (270 MHz) spectra of these porphyrins are presented.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 1066-1069

Synthesis of tetraphenylporphyrin molecules containing heteroatoms other than nitrogen. Part 4. Symmetrically and unsymmetrically substituted tetra phenyl-21,23-dithiaporphyrins

A. Ulman and J. Manassen, J. Chem. Soc., Perkin Trans. 1, 1979, 1066 DOI: 10.1039/P19790001066

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