Efficient sensitized photooxygenation in water by a porphyrin-cyclodextrin supramolecular complex.
[reaction: see text] The 2:1 inclusion complex between (2,3,6-tri-O-methyl)-beta-cyclodextrin (TMbetaCD) and 5,10,15,20-tetrakis(4-sulfonatophenyl)-porphyrin (TPPS(4)) 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 x 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.
Bonchio
Marcella
M
ITM CNR-sezione di Padova, Dipartimento di Chimica Organica, Università di Padova, via Marzolo 1, I-35131 Padova, Italy. marcella.bonchio@unipd.it
Carofiglio
Tommaso
T
Carraro
Mauro
M
Fornasier
Roberto
R
Tonellato
Umberto
U
D003505:Cyclodextrins / Q000737:chemistry*; D046911:Macromolecular Substances; D008715:Methionine / Q000031:analogs & derivatives / Q000737:chemistry / Q000528:radiation effects; D008954:Models, Biological; D010100:Oxygen / Q000737:chemistry*; D010777:Photochemistry; D017319:Photosensitizing Agents; D011166:Porphyrins / Q000737:chemistry*; D014466:Ultraviolet Rays; D014498:Uracil / Q000737:chemistry / Q000528:radiation effects; D014867:Water / Q000737:chemistry
D003505:Cyclodextrins; D046911:Macromolecular Substances; D017319:Photosensitizing Agents; D011166:Porphyrins; D014867:Water; C016136:tetraphenylporphine sulfonate; D014498:Uracil; D008715:Methionine; C038344:methionine methyl ester; D010100:Oxygen