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 (
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| Veröffentlicht in: | Organic letters 2002-12, Vol.4 (26), p.4635-4637 |
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| container_end_page | 4637 |
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| container_issue | 26 |
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| container_title | Organic letters |
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| creator | Bonchio, Marcella Carofiglio, Tommaso Carraro, Mauro Fornasier, Roberto Tonellato, Umberto |
| description | 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 ( |
| doi_str_mv | 10.1021/ol0270069 |
| format | Article |
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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.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0270069</identifier><identifier>PMID: 12489948</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cyclodextrins - chemistry ; Macromolecular Substances ; Methionine - analogs & derivatives ; Methionine - chemistry ; Methionine - radiation effects ; Models, Biological ; Oxygen - chemistry ; Photochemistry ; Photosensitizing Agents ; Porphyrins - chemistry ; Ultraviolet Rays ; Uracil - chemistry ; Uracil - radiation effects ; Water - chemistry</subject><ispartof>Organic letters, 2002-12, Vol.4 (26), p.4635-4637</ispartof><rights>Copyright © 2002 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-143988497935df90f6c541731edc7dccbc7f98856e6efdb375370396b7d0b62c3</citedby><cites>FETCH-LOGICAL-a377t-143988497935df90f6c541731edc7dccbc7f98856e6efdb375370396b7d0b62c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol0270069$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol0270069$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12489948$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bonchio, Marcella</creatorcontrib><creatorcontrib>Carofiglio, Tommaso</creatorcontrib><creatorcontrib>Carraro, Mauro</creatorcontrib><creatorcontrib>Fornasier, Roberto</creatorcontrib><creatorcontrib>Tonellato, Umberto</creatorcontrib><title>Efficient Sensitized Photooxygenation in Water by a Porphyrin−Cyclodextrin Supramolecular Complex</title><title>Organic letters</title><addtitle>Org. 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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.</description><subject>Cyclodextrins - chemistry</subject><subject>Macromolecular Substances</subject><subject>Methionine - analogs & derivatives</subject><subject>Methionine - chemistry</subject><subject>Methionine - radiation effects</subject><subject>Models, Biological</subject><subject>Oxygen - chemistry</subject><subject>Photochemistry</subject><subject>Photosensitizing Agents</subject><subject>Porphyrins - chemistry</subject><subject>Ultraviolet Rays</subject><subject>Uracil - chemistry</subject><subject>Uracil - radiation effects</subject><subject>Water - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKxDAUhoMojo4ufAHJRsHFaNK0TbOUMl5gwIFRXJY0PXUytE1NUpj6BK59RJ_EygzjxtW58J0Pzo_QGSXXlAT0xlQk4ITEYg8d0ShgE06iYH_Xx2SEjp1bEUKHjThEIxqEiRBhcoTUtCy10tB4vIDGaa8_oMDzpfHGrPs3aKTXpsG6wa_Sg8V5jyWeG9sue6ub78-vtFeVKWDthxEvutbK2lSgukpanJq6rWB9gg5KWTk43dYxermbPqcPk9nT_WN6O5tIxrmf0JCJJAkFFywqSkHKWEUh5YxCoXihVK54OQBRDDGURc54xDhhIs55QfI4UGyMLjfe1pr3DpzPau0UVJVswHQu4wHnCR3OxuhqAyprnLNQZq3VtbR9Rkn2m2i2S3Rgz7fSLq-h-CO3EQ7AxQaQymUr09lm-PEf0Q95A376</recordid><startdate>20021226</startdate><enddate>20021226</enddate><creator>Bonchio, Marcella</creator><creator>Carofiglio, Tommaso</creator><creator>Carraro, Mauro</creator><creator>Fornasier, Roberto</creator><creator>Tonellato, Umberto</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20021226</creationdate><title>Efficient Sensitized Photooxygenation in Water by a Porphyrin−Cyclodextrin Supramolecular Complex</title><author>Bonchio, Marcella ; Carofiglio, Tommaso ; Carraro, Mauro ; Fornasier, Roberto ; Tonellato, Umberto</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-143988497935df90f6c541731edc7dccbc7f98856e6efdb375370396b7d0b62c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Cyclodextrins - chemistry</topic><topic>Macromolecular Substances</topic><topic>Methionine - analogs & derivatives</topic><topic>Methionine - chemistry</topic><topic>Methionine - radiation effects</topic><topic>Models, Biological</topic><topic>Oxygen - chemistry</topic><topic>Photochemistry</topic><topic>Photosensitizing Agents</topic><topic>Porphyrins - chemistry</topic><topic>Ultraviolet Rays</topic><topic>Uracil - chemistry</topic><topic>Uracil - radiation effects</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bonchio, Marcella</creatorcontrib><creatorcontrib>Carofiglio, Tommaso</creatorcontrib><creatorcontrib>Carraro, Mauro</creatorcontrib><creatorcontrib>Fornasier, Roberto</creatorcontrib><creatorcontrib>Tonellato, Umberto</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bonchio, Marcella</au><au>Carofiglio, Tommaso</au><au>Carraro, Mauro</au><au>Fornasier, Roberto</au><au>Tonellato, Umberto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Sensitized Photooxygenation in Water by a Porphyrin−Cyclodextrin Supramolecular Complex</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2002-12-26</date><risdate>2002</risdate><volume>4</volume><issue>26</issue><spage>4635</spage><epage>4637</epage><pages>4635-4637</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12489948</pmid><doi>10.1021/ol0270069</doi><tpages>3</tpages></addata></record> |
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| ispartof | Organic letters, 2002-12, Vol.4 (26), p.4635-4637 |
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| source | MEDLINE; ACS Publications |
| subjects | Cyclodextrins - chemistry Macromolecular Substances Methionine - analogs & derivatives Methionine - chemistry Methionine - radiation effects Models, Biological Oxygen - chemistry Photochemistry Photosensitizing Agents Porphyrins - chemistry Ultraviolet Rays Uracil - chemistry Uracil - radiation effects Water - chemistry |
| title | Efficient Sensitized Photooxygenation in Water by a Porphyrin−Cyclodextrin Supramolecular Complex |
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