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

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

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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
Pages (from-to)19-29
Number of pages11
JournalJournal of the Brazilian Chemical Society
Volume7
Issue number1
Publication statusPublished - 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

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title = "Synthesis and fluorescence quenching studies of a series of carotenoporphyrins with carotenoids of various lengths",
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.",
keywords = "Carotenoporphyrins; carotenoid, Photoprotection, Porphyrin",
author = "Cardoso, {Sergio L.} and Nicodem, {David E.} and Moore, {Thomas A} and Moore, {Ana L} and Gust, {John Devens}",
year = "1996",
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T1 - Synthesis and fluorescence quenching studies of a series of carotenoporphyrins with carotenoids of various lengths

AU - Cardoso, Sergio L.

AU - Nicodem, David E.

AU - Moore, Thomas A

AU - Moore, Ana L

AU - Gust, John Devens

PY - 1996

Y1 - 1996

N2 - 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.

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.

KW - Carotenoporphyrins; carotenoid

KW - Photoprotection

KW - Porphyrin

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