Efficient Sensitized Photooxygenation in Water by a Porphyrin−Cyclodextrin Supramolecular Complex

The 2:1 inclusion complex between (2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCD) and 5,10,15,20-tetrakis(4-sulfonatophenyl)-porphyrin (TPPS4) behaves as a supramolecular sensitizer in water providing photooxygenation with turnover numbers up to 30 000 with a very minor sensitizer bleaching (<10%). T...

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Published inOrganic letters Vol. 4; no. 26; pp. 4635 - 4637
Main Authors Bonchio, Marcella, Carofiglio, Tommaso, Carraro, Mauro, Fornasier, Roberto, Tonellato, Umberto
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.12.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclodextrins - chemistry
Macromolecular Substances
Methionine - analogs & derivatives
Methionine - chemistry
Methionine - radiation effects
Models, Biological
Oxygen - chemistry
Photochemistry
Photosensitizing Agents
Physical Sciences
Porphyrins - chemistry
Science & Technology
Ultraviolet Rays
Uracil - chemistry
Uracil - radiation effects
Water - chemistry
OXIDATION
BETA-CYCLODEXTRIN
CHEMISTRY
SINGLET OXYGEN
PHENOL
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Summary:The 2:1 inclusion complex between (2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCD) and 5,10,15,20-tetrakis(4-sulfonatophenyl)-porphyrin (TPPS4) behaves as a supramolecular sensitizer in water providing photooxygenation with turnover numbers up to 30 000 with a very minor sensitizer bleaching (<10%). The protocol, which employs only 4 equiv of the cyclodextrin additive with respect to the porphyrin sensitizer (5 × 10-7 M), leads to high yield oxidation of model biomolecules such as l-methionine methyl ester and uracil and is also effective for phenol degradation in aqueous solution.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0270069