Oxidative Metalation as a Route to Size-Mismatched Macrocyclic Complexes: Osmium Corroles
Heavy‐element corroles are of great interest as optical sensors, near‐IR dyes, phosphors, organic light‐emitting diodes, and anticancer compounds. Insertion of 5d metals into corroles, however, is often a difficult and unpredictable process. Against this backdrop, oxidative metalation of meso triary...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-12, Vol.53 (52), p.14411-14414 |
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| creator | Alemayehu, Abraham B. Gagnon, Kevin J. Terner, James Ghosh, Abhik |
| description | Heavy‐element corroles are of great interest as optical sensors, near‐IR dyes, phosphors, organic light‐emitting diodes, and anticancer compounds. Insertion of 5d metals into corroles, however, is often a difficult and unpredictable process. Against this backdrop, oxidative metalation of meso triarylcorroles with [Os3(CO)12]/NaN3 in refluxing 1:2 diethylene glycol monomethyl ether/glycol has provided a convenient and relatively high‐yielding route to nitridoosmium(VI) corroles, three of which could be characterized with single‐crystal X‐ray structure analysis.
Last man standing! After the synthesis of platinum corroles, osmium was the last remaining middle and late 5d metal to be inserted into the contracted porphyrin analogue. Oxidative metalation has now provided a moderately high‐yielding route to osmium corroles. DEGME=diethylene glycol monomethyl ether. |
| doi_str_mv | 10.1002/anie.201405890 |
| format | Article |
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Last man standing! After the synthesis of platinum corroles, osmium was the last remaining middle and late 5d metal to be inserted into the contracted porphyrin analogue. Oxidative metalation has now provided a moderately high‐yielding route to osmium corroles. DEGME=diethylene glycol monomethyl ether.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201405890</identifier><identifier>PMID: 25346094</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>corroles ; Diodes ; Ethers ; Glycols ; Insertion ; Macrocyclic compounds ; metalation ; Optical sensors ; Osmium ; Phosphors ; Porphyrins ; Refluxing ; transition metals ; X-ray diffraction ; X-rays</subject><ispartof>Angewandte Chemie International Edition, 2014-12, Vol.53 (52), p.14411-14414</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5470-39583a358aefff38a38c3035472e55526b5596202e715e5901f9fafc27c54de33</citedby><cites>FETCH-LOGICAL-c5470-39583a358aefff38a38c3035472e55526b5596202e715e5901f9fafc27c54de33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201405890$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201405890$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25346094$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Alemayehu, Abraham B.</creatorcontrib><creatorcontrib>Gagnon, Kevin J.</creatorcontrib><creatorcontrib>Terner, James</creatorcontrib><creatorcontrib>Ghosh, Abhik</creatorcontrib><title>Oxidative Metalation as a Route to Size-Mismatched Macrocyclic Complexes: Osmium Corroles</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Heavy‐element corroles are of great interest as optical sensors, near‐IR dyes, phosphors, organic light‐emitting diodes, and anticancer compounds. Insertion of 5d metals into corroles, however, is often a difficult and unpredictable process. Against this backdrop, oxidative metalation of meso triarylcorroles with [Os3(CO)12]/NaN3 in refluxing 1:2 diethylene glycol monomethyl ether/glycol has provided a convenient and relatively high‐yielding route to nitridoosmium(VI) corroles, three of which could be characterized with single‐crystal X‐ray structure analysis.
Last man standing! After the synthesis of platinum corroles, osmium was the last remaining middle and late 5d metal to be inserted into the contracted porphyrin analogue. Oxidative metalation has now provided a moderately high‐yielding route to osmium corroles. DEGME=diethylene glycol monomethyl ether.</description><subject>corroles</subject><subject>Diodes</subject><subject>Ethers</subject><subject>Glycols</subject><subject>Insertion</subject><subject>Macrocyclic compounds</subject><subject>metalation</subject><subject>Optical sensors</subject><subject>Osmium</subject><subject>Phosphors</subject><subject>Porphyrins</subject><subject>Refluxing</subject><subject>transition metals</subject><subject>X-ray diffraction</subject><subject>X-rays</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkUtvEzEUhS0EoiWwZYkssWEzwY_xi10b2lKpaaRSQKws17kjXGbi1J6hCb8ej1IixKYrX9nfOVc-B6HXlEwpIey9WwWYMkJrIrQhT9AhFYxWXCn-tMw155XSgh6gFznfFl5rIp-jAyZ4LYmpD9H3xSYsXR9-AZ5D79oyxhV2GTt8FYcecB_x5_AbqnnInev9D1jiufMp-q1vg8ez2K1b2ED-gBe5C0NXblKKLeSX6Fnj2gyvHs4J-nJ6cj37VF0szs5nRxeVF7UiFTdCc8eFdtA0DdeOa88JL28MhBBM3ghhJCMMFBUgDKGNaVzjmSr6JXA-Qe92vusU7wbIve1C9tC2bgVxyJYqMiZltHocldzUxggxom__Q2_jkFblIyMlNZNjuBM03VElkJwTNHadQufS1lJix6127Mfu-ymCNw-2w00Hyz3-t5ACmB1wH1rYPmJnjy7PT_41r3bakHvY7LUu_bRScSXst8sz-_X4-ri-oh-t5H8AJ0CpRw</recordid><startdate>20141222</startdate><enddate>20141222</enddate><creator>Alemayehu, Abraham B.</creator><creator>Gagnon, Kevin J.</creator><creator>Terner, James</creator><creator>Ghosh, Abhik</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20141222</creationdate><title>Oxidative Metalation as a Route to Size-Mismatched Macrocyclic Complexes: Osmium Corroles</title><author>Alemayehu, Abraham B. ; Gagnon, Kevin J. ; Terner, James ; Ghosh, Abhik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5470-39583a358aefff38a38c3035472e55526b5596202e715e5901f9fafc27c54de33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>corroles</topic><topic>Diodes</topic><topic>Ethers</topic><topic>Glycols</topic><topic>Insertion</topic><topic>Macrocyclic compounds</topic><topic>metalation</topic><topic>Optical sensors</topic><topic>Osmium</topic><topic>Phosphors</topic><topic>Porphyrins</topic><topic>Refluxing</topic><topic>transition metals</topic><topic>X-ray diffraction</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alemayehu, Abraham B.</creatorcontrib><creatorcontrib>Gagnon, Kevin J.</creatorcontrib><creatorcontrib>Terner, James</creatorcontrib><creatorcontrib>Ghosh, Abhik</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alemayehu, Abraham B.</au><au>Gagnon, Kevin J.</au><au>Terner, James</au><au>Ghosh, Abhik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Metalation as a Route to Size-Mismatched Macrocyclic Complexes: Osmium Corroles</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-12-22</date><risdate>2014</risdate><volume>53</volume><issue>52</issue><spage>14411</spage><epage>14414</epage><pages>14411-14414</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Heavy‐element corroles are of great interest as optical sensors, near‐IR dyes, phosphors, organic light‐emitting diodes, and anticancer compounds. Insertion of 5d metals into corroles, however, is often a difficult and unpredictable process. Against this backdrop, oxidative metalation of meso triarylcorroles with [Os3(CO)12]/NaN3 in refluxing 1:2 diethylene glycol monomethyl ether/glycol has provided a convenient and relatively high‐yielding route to nitridoosmium(VI) corroles, three of which could be characterized with single‐crystal X‐ray structure analysis.
Last man standing! After the synthesis of platinum corroles, osmium was the last remaining middle and late 5d metal to be inserted into the contracted porphyrin analogue. Oxidative metalation has now provided a moderately high‐yielding route to osmium corroles. DEGME=diethylene glycol monomethyl ether.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25346094</pmid><doi>10.1002/anie.201405890</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | corroles Diodes Ethers Glycols Insertion Macrocyclic compounds metalation Optical sensors Osmium Phosphors Porphyrins Refluxing transition metals X-ray diffraction X-rays |
| title | Oxidative Metalation as a Route to Size-Mismatched Macrocyclic Complexes: Osmium Corroles |
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