Large Substituent Effect on the Photochemical Rearrangement of 1,6-(N-Aryl)aza-[60]fulleroids to 1,2-(N-Arylaziridino)-[60]fullerenes
Large substituent effects were observed in the rates and reaction mechanisms of the photochemical rearrangement of N-arylaza-[60]fulleroid 1 to N-arylaziridino-[60]fullerene 2, in which the difference of the rates between the fastest and the slowest (>2160-fold) was attained only by changing the...
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| Veröffentlicht in: | Journal of the American Chemical Society 2002-11, Vol.124 (45), p.13364-13365 |
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| container_issue | 45 |
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| container_title | Journal of the American Chemical Society |
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| creator | Ouchi, Akihiko Hatsuda, Ryota Awen, Bahlul Z. S Sakuragi, Masako Ogura, Reiko Ishii, Tadahiro Araki, Yasuyuki Ito, Osamu |
| description | Large substituent effects were observed in the rates and reaction mechanisms of the photochemical rearrangement of N-arylaza-[60]fulleroid 1 to N-arylaziridino-[60]fullerene 2, in which the difference of the rates between the fastest and the slowest (>2160-fold) was attained only by changing the aryl group from 1-naphthyl to 2-naphthyl. The decreasing order of the reaction rates in relation to the substituents was 1-naphthyl (1b) > 1-pyrenyl (1d) > phenyl (1a) > 2-naphthyl (1c). The reactions proceeded via triplet states of the fulleroids and a triplet sensitization of the reaction by rearranged product 2b was observed in the case of 1b. The slow reactions of 1a,c were interpretated by the participation of charge-separated species in the excited triplet states, which was supported by nanosecond transient absorption spectra. |
| doi_str_mv | 10.1021/ja0267728 |
| format | Article |
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The slow reactions of 1a,c were interpretated by the participation of charge-separated species in the excited triplet states, which was supported by nanosecond transient absorption spectra.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0267728</identifier><identifier>PMID: 12418871</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; General and physical chemistry ; Photochemistry ; Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><ispartof>Journal of the American Chemical Society, 2002-11, Vol.124 (45), p.13364-13365</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-62a36bde6a5b6eb26cac1e514d8d3b24fb05c91e05c398e218b6dbf2bf79cba83</citedby><cites>FETCH-LOGICAL-a445t-62a36bde6a5b6eb26cac1e514d8d3b24fb05c91e05c398e218b6dbf2bf79cba83</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/ja0267728$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0267728$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14008816$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12418871$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ouchi, Akihiko</creatorcontrib><creatorcontrib>Hatsuda, Ryota</creatorcontrib><creatorcontrib>Awen, Bahlul Z. 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The reactions proceeded via triplet states of the fulleroids and a triplet sensitization of the reaction by rearranged product 2b was observed in the case of 1b. The slow reactions of 1a,c were interpretated by the participation of charge-separated species in the excited triplet states, which was supported by nanosecond transient absorption spectra.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Photochemistry</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNpt0M9rFDEUwPEgil2rB_8BmYvFBUeTzEwmeyxL_YGLLraCIBJeMi_drDOTmmTA9u7_bcquXQ9eEsL78AhfQp4y-opRzl5vgXLRtlzeIzPWcFo2jIv7ZEYp5WUrRXVEHsW4zc-aS_aQHDFeMylbNiO_VxAusTifdEwuTTim4sxaNKnwY5E2WKw3PnmzwcEZ6IvPCCHAeInDrfS2YC9F-eJjeRqu-zncQPlN0O926nsM3nWxSD4L_lfAjQuuc6Of_-NwxPiYPLDQR3yyv4_JlzdnF8t35erT2_fL01UJdd2kUnCohO5QQKMFai4MGIYNqzvZVZrXVtPGLBjms1pI5Exq0WnLtW0XRoOsjsnJbu9V8D8njEkNLhrsexjRT1G1XDT1ol1kON9BE3yMAa26Cm6AcK0YVbfN1V3zbJ_tl056wO4g95EzeL4HEHNEmwMaFw-uplRKJrIrd87FhL_u5hB-KNFWbaMu1udKrL6uq2b5Qa0Pe8FEtfVTGHO7_3zwD_B2o8U</recordid><startdate>20021113</startdate><enddate>20021113</enddate><creator>Ouchi, Akihiko</creator><creator>Hatsuda, Ryota</creator><creator>Awen, Bahlul Z. 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S</creatorcontrib><creatorcontrib>Sakuragi, Masako</creatorcontrib><creatorcontrib>Ogura, Reiko</creatorcontrib><creatorcontrib>Ishii, Tadahiro</creatorcontrib><creatorcontrib>Araki, Yasuyuki</creatorcontrib><creatorcontrib>Ito, Osamu</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ouchi, Akihiko</au><au>Hatsuda, Ryota</au><au>Awen, Bahlul Z. S</au><au>Sakuragi, Masako</au><au>Ogura, Reiko</au><au>Ishii, Tadahiro</au><au>Araki, Yasuyuki</au><au>Ito, Osamu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Large Substituent Effect on the Photochemical Rearrangement of 1,6-(N-Aryl)aza-[60]fulleroids to 1,2-(N-Arylaziridino)-[60]fullerenes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2002-11-13</date><risdate>2002</risdate><volume>124</volume><issue>45</issue><spage>13364</spage><epage>13365</epage><pages>13364-13365</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Large substituent effects were observed in the rates and reaction mechanisms of the photochemical rearrangement of N-arylaza-[60]fulleroid 1 to N-arylaziridino-[60]fullerene 2, in which the difference of the rates between the fastest and the slowest (>2160-fold) was attained only by changing the aryl group from 1-naphthyl to 2-naphthyl. The decreasing order of the reaction rates in relation to the substituents was 1-naphthyl (1b) > 1-pyrenyl (1d) > phenyl (1a) > 2-naphthyl (1c). The reactions proceeded via triplet states of the fulleroids and a triplet sensitization of the reaction by rearranged product 2b was observed in the case of 1b. The slow reactions of 1a,c were interpretated by the participation of charge-separated species in the excited triplet states, which was supported by nanosecond transient absorption spectra.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12418871</pmid><doi>10.1021/ja0267728</doi><tpages>2</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology General and physical chemistry Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) |
| title | Large Substituent Effect on the Photochemical Rearrangement of 1,6-(N-Aryl)aza-[60]fulleroids to 1,2-(N-Arylaziridino)-[60]fullerenes |
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