Extremely Photostable Electron‐Deficient Phthalocyanines that Generate High Levels of Singlet Oxygen
A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents...
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| Veröffentlicht in: | Chemistry : a European journal 2019-02, Vol.25 (7), p.1678-1682 |
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| container_end_page | 1682 |
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| container_issue | 7 |
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| container_title | Chemistry : a European journal |
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| creator | Furuyama, Taniyuki Miyaji, Yusuke Maeda, Kazuya Maeda, Hajime Segi, Masahito |
| description | A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents. Upon irradiation with red light, some of the thus‐obtained metal complexes generated high levels of singlet oxygen. In particular, a palladium complex exhibited attractive photostability upon exposure to singlet oxygen as a bleaching agent. The photostability of such complexes that may manifest concomitantly to the generation of high levels of singlet oxygen was attributed to the presence of the electron‐withdrawing groups, which results in energetically low‐lying highest occupied molecular orbitals.
A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents. |
| doi_str_mv | 10.1002/chem.201805082 |
| format | Article |
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A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201805082</identifier><identifier>PMID: 30457173</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Bleaching ; Chemistry ; Coordination compounds ; electron-withdrawing group ; Electrons ; Irradiation ; lead ; Metal complexes ; Molecular orbitals ; Oxygen ; Palladium ; photostability ; phthalocyanine ; Radiation ; Singlet oxygen</subject><ispartof>Chemistry : a European journal, 2019-02, Vol.25 (7), p.1678-1682</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4102-90d48d7a67a329ba827bf63d7294aa99c2ad21250357e728bf6d451b5a79a22b3</citedby><cites>FETCH-LOGICAL-c4102-90d48d7a67a329ba827bf63d7294aa99c2ad21250357e728bf6d451b5a79a22b3</cites><orcidid>0000-0002-5435-1581</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201805082$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201805082$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30457173$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Furuyama, Taniyuki</creatorcontrib><creatorcontrib>Miyaji, Yusuke</creatorcontrib><creatorcontrib>Maeda, Kazuya</creatorcontrib><creatorcontrib>Maeda, Hajime</creatorcontrib><creatorcontrib>Segi, Masahito</creatorcontrib><title>Extremely Photostable Electron‐Deficient Phthalocyanines that Generate High Levels of Singlet Oxygen</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents. Upon irradiation with red light, some of the thus‐obtained metal complexes generated high levels of singlet oxygen. In particular, a palladium complex exhibited attractive photostability upon exposure to singlet oxygen as a bleaching agent. The photostability of such complexes that may manifest concomitantly to the generation of high levels of singlet oxygen was attributed to the presence of the electron‐withdrawing groups, which results in energetically low‐lying highest occupied molecular orbitals.
A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents.</description><subject>Bleaching</subject><subject>Chemistry</subject><subject>Coordination compounds</subject><subject>electron-withdrawing group</subject><subject>Electrons</subject><subject>Irradiation</subject><subject>lead</subject><subject>Metal complexes</subject><subject>Molecular orbitals</subject><subject>Oxygen</subject><subject>Palladium</subject><subject>photostability</subject><subject>phthalocyanine</subject><subject>Radiation</subject><subject>Singlet oxygen</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqF0cFu1DAQBmALUdGlcOWILHHhkq09juP4iJali7RVkYBz5CST3VSOXWwvNDcegWfkSXC1pUi9cLJG_vxr5J-QV5wtOWNw3u1xWgLjNZOshidkwSXwQqhKPiULpktVVFLoU_I8xmvGmK6EeEZOBSul4kosyLC-TQEntDP9tPfJx2Rai3RtsUvBu98_f73HYexGdCmDtDfWd7Nxo8NI85ToBToMJiHdjLs93eJ3tJH6gX4e3c5iole38w7dC3IyGBvx5f15Rr5-WH9ZbYrt1cXH1btt0ZWcQaFZX9a9MpUyAnRralDtUIlegS6N0boD0wMHyYRUqKDOl30peSuN0gagFWfk7TH3JvhvB4ypmcbYobXGoT_EBrioWAVcsUzfPKLX_hBc3i4rVfJKAddZLY-qCz7GgENzE8bJhLnhrLlroLlroHloID94fR97aCfsH_jfL89AH8GP0eL8n7hmtVlf_gv_A7lZkxE</recordid><startdate>20190201</startdate><enddate>20190201</enddate><creator>Furuyama, Taniyuki</creator><creator>Miyaji, Yusuke</creator><creator>Maeda, Kazuya</creator><creator>Maeda, Hajime</creator><creator>Segi, Masahito</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5435-1581</orcidid></search><sort><creationdate>20190201</creationdate><title>Extremely Photostable Electron‐Deficient Phthalocyanines that Generate High Levels of Singlet Oxygen</title><author>Furuyama, Taniyuki ; Miyaji, Yusuke ; Maeda, Kazuya ; Maeda, Hajime ; Segi, Masahito</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4102-90d48d7a67a329ba827bf63d7294aa99c2ad21250357e728bf6d451b5a79a22b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Bleaching</topic><topic>Chemistry</topic><topic>Coordination compounds</topic><topic>electron-withdrawing group</topic><topic>Electrons</topic><topic>Irradiation</topic><topic>lead</topic><topic>Metal complexes</topic><topic>Molecular orbitals</topic><topic>Oxygen</topic><topic>Palladium</topic><topic>photostability</topic><topic>phthalocyanine</topic><topic>Radiation</topic><topic>Singlet oxygen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Furuyama, Taniyuki</creatorcontrib><creatorcontrib>Miyaji, Yusuke</creatorcontrib><creatorcontrib>Maeda, Kazuya</creatorcontrib><creatorcontrib>Maeda, Hajime</creatorcontrib><creatorcontrib>Segi, Masahito</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Furuyama, Taniyuki</au><au>Miyaji, Yusuke</au><au>Maeda, Kazuya</au><au>Maeda, Hajime</au><au>Segi, Masahito</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Extremely Photostable Electron‐Deficient Phthalocyanines that Generate High Levels of Singlet Oxygen</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2019-02-01</date><risdate>2019</risdate><volume>25</volume><issue>7</issue><spage>1678</spage><epage>1682</epage><pages>1678-1682</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents. Upon irradiation with red light, some of the thus‐obtained metal complexes generated high levels of singlet oxygen. In particular, a palladium complex exhibited attractive photostability upon exposure to singlet oxygen as a bleaching agent. The photostability of such complexes that may manifest concomitantly to the generation of high levels of singlet oxygen was attributed to the presence of the electron‐withdrawing groups, which results in energetically low‐lying highest occupied molecular orbitals.
A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30457173</pmid><doi>10.1002/chem.201805082</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5435-1581</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Bleaching Chemistry Coordination compounds electron-withdrawing group Electrons Irradiation lead Metal complexes Molecular orbitals Oxygen Palladium photostability phthalocyanine Radiation Singlet oxygen |
| title | Extremely Photostable Electron‐Deficient Phthalocyanines that Generate High Levels of Singlet Oxygen |
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