Synthesis and fluorescence quenching studies of a series of carotenoporphyrins with carotenoids of various lengths

Sergio L. Cardoso, David E. Nicodem, Thomas Moore, Ana Moore, Devens Gust

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A series of molecular dyads, each consisting of a porphyrin covalently linked to a carotenoid, was synthesized. The carotenoid conjugated chain length was systematically varied from 5 to 11 double bonds (not including the carbonyl group) and each carotenoid was linked to 5-(4-aminophenyl)-10,15,20-tris(4-methylphenyl)porphyrin (TPPA) by an amide bond. The analogous zinc carotenoporphyrins were prepared by metallation of the free base species. Porphyrin fluorescence quenching by the carotenoids was studied as a function of the length of the carotenoid conjugated system. Carotenoids containing from 5 to 7 double bonds do not quench porphyrin fluorescence. Carotenoids with 10 or 11 double bonds quench the fluorescence of the attached porphyrin to ∼10% of the value of the parent porphyrin, and carotenoids with 8 or 9 double bonds exhibit an intermediate quenching effect that is solvent dependent. In the intermediate cases greater fluorescence quenching is observed for the zinc carotenoporphyrins.

Original languageEnglish (US)
Pages (from-to)19-29
Number of pages11
JournalJournal of the Brazilian Chemical Society
Volume7
Issue number1
StatePublished - 1996

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Carotenoids
Quenching
Porphyrins
Fluorescence
Zinc
Chain length
Amides

Keywords

  • Carotenoporphyrins; carotenoid
  • Photoprotection
  • Porphyrin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and fluorescence quenching studies of a series of carotenoporphyrins with carotenoids of various lengths. / Cardoso, Sergio L.; Nicodem, David E.; Moore, Thomas; Moore, Ana; Gust, Devens.

In: Journal of the Brazilian Chemical Society, Vol. 7, No. 1, 1996, p. 19-29.

Research output: Contribution to journalArticle

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AB - A series of molecular dyads, each consisting of a porphyrin covalently linked to a carotenoid, was synthesized. The carotenoid conjugated chain length was systematically varied from 5 to 11 double bonds (not including the carbonyl group) and each carotenoid was linked to 5-(4-aminophenyl)-10,15,20-tris(4-methylphenyl)porphyrin (TPPA) by an amide bond. The analogous zinc carotenoporphyrins were prepared by metallation of the free base species. Porphyrin fluorescence quenching by the carotenoids was studied as a function of the length of the carotenoid conjugated system. Carotenoids containing from 5 to 7 double bonds do not quench porphyrin fluorescence. Carotenoids with 10 or 11 double bonds quench the fluorescence of the attached porphyrin to ∼10% of the value of the parent porphyrin, and carotenoids with 8 or 9 double bonds exhibit an intermediate quenching effect that is solvent dependent. In the intermediate cases greater fluorescence quenching is observed for the zinc carotenoporphyrins.

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