Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties
Unprecedented neutral perylene‐3,4:9,10‐tetracarboxylic acid bisimide (PBI) radicals and biradicals were synthesized by facile chemical oxidation of 4‐hydroxyaryl‐substituted PBIs. Subsequent characterization by optical and magnetic spectroscopic techniques, as well as quantum chemical calculations,...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-11, Vol.54 (47), p.13980-13984 |
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| container_issue | 47 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Schmidt, David Son, Minjung Lim, Jong Min Lin, Mei-Jin Krummenacher, Ivo Braunschweig, Holger Kim, Dongho Würthner, Frank |
| description | Unprecedented neutral perylene‐3,4:9,10‐tetracarboxylic acid bisimide (PBI) radicals and biradicals were synthesized by facile chemical oxidation of 4‐hydroxyaryl‐substituted PBIs. Subsequent characterization by optical and magnetic spectroscopic techniques, as well as quantum chemical calculations, revealed an open‐shell singlet biradical ground state for the PBI biradical OS‐2.. (〈s2〉=1.2191) with a relatively small singlet–triplet energy gap of 0.041 eV and a large singlet biradical character of y=0.72.
Stable biradicals: A singlet open‐shell perylene bisimide (PBI) biradical was generated by facile chemical oxidation of a 4‐hydroxyaryl‐substituted PBI. The remarkable stability of OS‐2.. facilitates its unambiguous characterization, revealing a large singlet biradical character of y=0.72. |
| doi_str_mv | 10.1002/anie.201507039 |
| format | Article |
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Stable biradicals: A singlet open‐shell perylene bisimide (PBI) biradical was generated by facile chemical oxidation of a 4‐hydroxyaryl‐substituted PBI. The remarkable stability of OS‐2.. facilitates its unambiguous characterization, revealing a large singlet biradical character of y=0.72.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201507039</identifier><identifier>PMID: 26350026</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>biradicals ; dyes ; perylene bisimides ; pigments ; radicals</subject><ispartof>Angewandte Chemie International Edition, 2015-11, Vol.54 (47), p.13980-13984</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6249-f887ff5d102e48b906c9f27e4832e3e77660a99c6b3a927cd97fb0721b531ff63</citedby><cites>FETCH-LOGICAL-c6249-f887ff5d102e48b906c9f27e4832e3e77660a99c6b3a927cd97fb0721b531ff63</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.201507039$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201507039$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26350026$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schmidt, David</creatorcontrib><creatorcontrib>Son, Minjung</creatorcontrib><creatorcontrib>Lim, Jong Min</creatorcontrib><creatorcontrib>Lin, Mei-Jin</creatorcontrib><creatorcontrib>Krummenacher, Ivo</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><creatorcontrib>Kim, Dongho</creatorcontrib><creatorcontrib>Würthner, Frank</creatorcontrib><title>Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Unprecedented neutral perylene‐3,4:9,10‐tetracarboxylic acid bisimide (PBI) radicals and biradicals were synthesized by facile chemical oxidation of 4‐hydroxyaryl‐substituted PBIs. Subsequent characterization by optical and magnetic spectroscopic techniques, as well as quantum chemical calculations, revealed an open‐shell singlet biradical ground state for the PBI biradical OS‐2.. (〈s2〉=1.2191) with a relatively small singlet–triplet energy gap of 0.041 eV and a large singlet biradical character of y=0.72.
Stable biradicals: A singlet open‐shell perylene bisimide (PBI) biradical was generated by facile chemical oxidation of a 4‐hydroxyaryl‐substituted PBI. The remarkable stability of OS‐2.. facilitates its unambiguous characterization, revealing a large singlet biradical character of y=0.72.</description><subject>biradicals</subject><subject>dyes</subject><subject>perylene bisimides</subject><subject>pigments</subject><subject>radicals</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkEtP4zAURq0RaIDObFmiSGxmk-JH_WLHVBAq8dIAmqXlJNfCkCbFbgT99xilVIgNK99rn--TdRDaJ3hMMKZHtvUwpphwLDHTP9Au4ZTkTEq2leYJY7lUnOygvRgfE68UFj_RDhWMp03sossbCKsGWsj--ujnvobsn619ZZuY2bZOt2G9Hme3q3b5ANEPL5ddA1Xf2JDdhG4BYekh_kLbLqHwe32O0P3Z6d30PL-4LmbTk4u8EnSic6eUdI7XBFOYqFJjUWlHZZoZBQZSCoGt1pUomdVUVrWWrsSSkpIz4pxgI_Rn6F2E7rmHuDRzHytoGttC10dDpMBKM85VQg-_oI9dH9r0u0RxmbQpzBI1HqgqdDEGcGYR_NyGlSHYvIs276LNRnQKHKxr-3IO9Qb_MJsAPQAvvoHVN3Xm5Gp2-rk8H7I-LuF1k7XhyQjJJDf_rwojikKKKb01BXsDHI-Xcg</recordid><startdate>20151116</startdate><enddate>20151116</enddate><creator>Schmidt, David</creator><creator>Son, Minjung</creator><creator>Lim, Jong Min</creator><creator>Lin, Mei-Jin</creator><creator>Krummenacher, Ivo</creator><creator>Braunschweig, Holger</creator><creator>Kim, Dongho</creator><creator>Würthner, Frank</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></search><sort><creationdate>20151116</creationdate><title>Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties</title><author>Schmidt, David ; Son, Minjung ; Lim, Jong Min ; Lin, Mei-Jin ; Krummenacher, Ivo ; Braunschweig, Holger ; Kim, Dongho ; Würthner, Frank</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6249-f887ff5d102e48b906c9f27e4832e3e77660a99c6b3a927cd97fb0721b531ff63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>biradicals</topic><topic>dyes</topic><topic>perylene bisimides</topic><topic>pigments</topic><topic>radicals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schmidt, David</creatorcontrib><creatorcontrib>Son, Minjung</creatorcontrib><creatorcontrib>Lim, Jong Min</creatorcontrib><creatorcontrib>Lin, Mei-Jin</creatorcontrib><creatorcontrib>Krummenacher, Ivo</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><creatorcontrib>Kim, Dongho</creatorcontrib><creatorcontrib>Würthner, Frank</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><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schmidt, David</au><au>Son, Minjung</au><au>Lim, Jong Min</au><au>Lin, Mei-Jin</au><au>Krummenacher, Ivo</au><au>Braunschweig, Holger</au><au>Kim, Dongho</au><au>Würthner, Frank</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-11-16</date><risdate>2015</risdate><volume>54</volume><issue>47</issue><spage>13980</spage><epage>13984</epage><pages>13980-13984</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Unprecedented neutral perylene‐3,4:9,10‐tetracarboxylic acid bisimide (PBI) radicals and biradicals were synthesized by facile chemical oxidation of 4‐hydroxyaryl‐substituted PBIs. Subsequent characterization by optical and magnetic spectroscopic techniques, as well as quantum chemical calculations, revealed an open‐shell singlet biradical ground state for the PBI biradical OS‐2.. (〈s2〉=1.2191) with a relatively small singlet–triplet energy gap of 0.041 eV and a large singlet biradical character of y=0.72.
Stable biradicals: A singlet open‐shell perylene bisimide (PBI) biradical was generated by facile chemical oxidation of a 4‐hydroxyaryl‐substituted PBI. The remarkable stability of OS‐2.. facilitates its unambiguous characterization, revealing a large singlet biradical character of y=0.72.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26350026</pmid><doi>10.1002/anie.201507039</doi><tpages>5</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| subjects | biradicals dyes perylene bisimides pigments radicals |
| title | Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties |
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