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

Abraham Ulman, Joost Manassen

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Abstract

The synthesis of symmetrically as well as unsymmetrically substituted tetraphenyl-21,23-dithiaporphyrins (S 2TPP) is described. The reaction of 2,5-dilithiothiophen with substituted benzaldehydes is used for the preparation of substituted 2,5-bis(phenylhydroxymethyl)thiophens. Symmetrically substituted S 2TPP molecules result from reaction of these dialcohols with equimolar quantities of pyrrole. Unsymmetrically substituted S 2TPP 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)-y, S-bis-(p-methoxyphenyl)-.anda,ß-bis-(p-fluorophenyl)-y, 8-bis-(p-methoxyphenyl)-por-phyrins. The optical and 1H n.m.r. (270 MHz) spectra of these porphyrins are presented.

Original languageEnglish (US)
Pages (from-to)1066-1069
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1979

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Pyrroles
Nitrogen
Benzaldehydes
Molecules
Porphyrins
diphenyl
tetraphenylporphyrin
21,23-dithiaporphyrin

ASJC Scopus subject areas

  • Chemistry(all)

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title = "Synthesis of tetraphenylporphyrin molecules containing heteroatoms other than nitrogen. Part 4. Symmetrically and unsymmetrically substituted tetraphenyl-21,23-dithiaporphyrins",
abstract = "The synthesis of symmetrically as well as unsymmetrically substituted tetraphenyl-21,23-dithiaporphyrins (S 2TPP) is described. The reaction of 2,5-dilithiothiophen with substituted benzaldehydes is used for the preparation of substituted 2,5-bis(phenylhydroxymethyl)thiophens. Symmetrically substituted S 2TPP molecules result from reaction of these dialcohols with equimolar quantities of pyrrole. Unsymmetrically substituted S 2TPP 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)-y, S-bis-(p-methoxyphenyl)-.anda,{\ss}-bis-(p-fluorophenyl)-y, 8-bis-(p-methoxyphenyl)-por-phyrins. The optical and 1H n.m.r. (270 MHz) spectra of these porphyrins are presented.",
author = "Abraham Ulman and Joost Manassen",
year = "1979",
language = "English (US)",
pages = "1066--1069",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",

}

TY - JOUR

T1 - Synthesis of tetraphenylporphyrin molecules containing heteroatoms other than nitrogen. Part 4. Symmetrically and unsymmetrically substituted tetraphenyl-21,23-dithiaporphyrins

AU - Ulman, Abraham

AU - Manassen, Joost

PY - 1979

Y1 - 1979

N2 - The synthesis of symmetrically as well as unsymmetrically substituted tetraphenyl-21,23-dithiaporphyrins (S 2TPP) is described. The reaction of 2,5-dilithiothiophen with substituted benzaldehydes is used for the preparation of substituted 2,5-bis(phenylhydroxymethyl)thiophens. Symmetrically substituted S 2TPP molecules result from reaction of these dialcohols with equimolar quantities of pyrrole. Unsymmetrically substituted S 2TPP 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)-y, S-bis-(p-methoxyphenyl)-.anda,ß-bis-(p-fluorophenyl)-y, 8-bis-(p-methoxyphenyl)-por-phyrins. The optical and 1H n.m.r. (270 MHz) spectra of these porphyrins are presented.

AB - The synthesis of symmetrically as well as unsymmetrically substituted tetraphenyl-21,23-dithiaporphyrins (S 2TPP) is described. The reaction of 2,5-dilithiothiophen with substituted benzaldehydes is used for the preparation of substituted 2,5-bis(phenylhydroxymethyl)thiophens. Symmetrically substituted S 2TPP molecules result from reaction of these dialcohols with equimolar quantities of pyrrole. Unsymmetrically substituted S 2TPP 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)-y, S-bis-(p-methoxyphenyl)-.anda,ß-bis-(p-fluorophenyl)-y, 8-bis-(p-methoxyphenyl)-por-phyrins. The optical and 1H n.m.r. (270 MHz) spectra of these porphyrins are presented.

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