Synthesis, Structure, and Physical Properties of 5,7,14,16-Tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene
A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized through a retro‐Diels–Alder reaction. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The HOMO–LUMO gap of TBH calculate...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2012-03, Vol.7 (3), p.561-564 |
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| creator | Xiao, Jinchong Liu, Shuwei Liu, Yi Ji, Li Liu, Xuewei Zhang, Hua Sun, Xiaowei Zhang, Qichun |
| description | A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized through a retro‐Diels–Alder reaction. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The HOMO–LUMO gap of TBH calculated from the difference between the half‐wave redox potentials (E1/2ox=+0.40 eV and E1/2red=−1.78 eV) is 2.18 eV, which is in good agreement with the band gap (2.19 eV) derived from the UV/Vis absorption data. In addition, organic light‐emitting devices using TBH as emitter have been fabricated. The results revealed that TBH is a promising red light‐emitting candidate for applications in organic light‐emitting diodes.
There is a twist: A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The electrochemical characteristics of TBH and data of fabricated organic light‐emitting devices using TBH as emitter suggest that TBH is a promising red light‐emitting candidate for applications in organic light‐emitting diodes. |
| doi_str_mv | 10.1002/asia.201100733 |
| format | Article |
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There is a twist: A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The electrochemical characteristics of TBH and data of fabricated organic light‐emitting devices using TBH as emitter suggest that TBH is a promising red light‐emitting candidate for applications in organic light‐emitting diodes.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201100733</identifier><identifier>PMID: 22223424</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Chemistry ; Hydrocarbons, Aromatic - chemical synthesis ; Hydrocarbons, Aromatic - chemistry ; Models, Molecular ; Molecular Structure ; OLED ; semiconductors ; structure elucidation ; synthetic methods ; Terphenyl Compounds - chemical synthesis ; Terphenyl Compounds - chemistry ; twistacene</subject><ispartof>Chemistry, an Asian journal, 2012-03, Vol.7 (3), p.561-564</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4763-794008518fdf984ae61b5c7ea7a7a7ab59137212b03b6b5d0539bfdc0f302aca3</citedby><cites>FETCH-LOGICAL-c4763-794008518fdf984ae61b5c7ea7a7a7ab59137212b03b6b5d0539bfdc0f302aca3</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%2Fasia.201100733$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201100733$$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/22223424$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xiao, Jinchong</creatorcontrib><creatorcontrib>Liu, Shuwei</creatorcontrib><creatorcontrib>Liu, Yi</creatorcontrib><creatorcontrib>Ji, Li</creatorcontrib><creatorcontrib>Liu, Xuewei</creatorcontrib><creatorcontrib>Zhang, Hua</creatorcontrib><creatorcontrib>Sun, Xiaowei</creatorcontrib><creatorcontrib>Zhang, Qichun</creatorcontrib><title>Synthesis, Structure, and Physical Properties of 5,7,14,16-Tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene</title><title>Chemistry, an Asian journal</title><addtitle>Chemistry - An Asian Journal</addtitle><description>A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized through a retro‐Diels–Alder reaction. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The HOMO–LUMO gap of TBH calculated from the difference between the half‐wave redox potentials (E1/2ox=+0.40 eV and E1/2red=−1.78 eV) is 2.18 eV, which is in good agreement with the band gap (2.19 eV) derived from the UV/Vis absorption data. In addition, organic light‐emitting devices using TBH as emitter have been fabricated. The results revealed that TBH is a promising red light‐emitting candidate for applications in organic light‐emitting diodes.
There is a twist: A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The electrochemical characteristics of TBH and data of fabricated organic light‐emitting devices using TBH as emitter suggest that TBH is a promising red light‐emitting candidate for applications in organic light‐emitting diodes.</description><subject>Chemistry</subject><subject>Hydrocarbons, Aromatic - chemical synthesis</subject><subject>Hydrocarbons, Aromatic - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>OLED</subject><subject>semiconductors</subject><subject>structure elucidation</subject><subject>synthetic methods</subject><subject>Terphenyl Compounds - chemical synthesis</subject><subject>Terphenyl Compounds - chemistry</subject><subject>twistacene</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1v1DAQxS0Eoh9w5YgiceCSLB47ju3eVhVsW1Ww0hbBzXKSieKSTRY7UZv-9bhsWSEu2AePpd97Gr1HyBugC6CUfbDB2QWjED-S82fkGFQBWS7h-_PDzNQROQnhllLBqFYvyRGLh-csPybtZu7HFoMLabIZ_VSNk8c0sX2drNs5uMp2ydoPO_Sjw5AMTSJSmUKeQpHd4OjtrsV-7jJ1plNgZ8Cz0oUS-4cha_HejncujLbCHl-RF43tAr5-ek_J108fb84vsusvq8vz5XVW5bLgmdQ5pUqAaupGq9xiAaWoJFr5-5ZCA5cMWEl5WZSipoLrsqkr2nDKbGX5KXm_99354eeEYTRbFyrsOtvjMAWjmZAgQbFIvvuHvB0m38flDIiIcJ2zIlKLPVX5IQSPjdl5t7V-NkDNYwXmsQJzqCAK3j7ZTuUW6wP-J_MI6D1w5zqc_2NnlpvL5d_m2V4bY8X7g9b6H6aQXArz7fPKqPUFXBVyZa74L-NInzc</recordid><startdate>20120305</startdate><enddate>20120305</enddate><creator>Xiao, Jinchong</creator><creator>Liu, Shuwei</creator><creator>Liu, Yi</creator><creator>Ji, Li</creator><creator>Liu, Xuewei</creator><creator>Zhang, Hua</creator><creator>Sun, Xiaowei</creator><creator>Zhang, Qichun</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>K9.</scope><scope>7X8</scope></search><sort><creationdate>20120305</creationdate><title>Synthesis, Structure, and Physical Properties of 5,7,14,16-Tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene</title><author>Xiao, Jinchong ; Liu, Shuwei ; Liu, Yi ; Ji, Li ; Liu, Xuewei ; Zhang, Hua ; Sun, Xiaowei ; Zhang, Qichun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4763-794008518fdf984ae61b5c7ea7a7a7ab59137212b03b6b5d0539bfdc0f302aca3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Chemistry</topic><topic>Hydrocarbons, Aromatic - chemical synthesis</topic><topic>Hydrocarbons, Aromatic - chemistry</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>OLED</topic><topic>semiconductors</topic><topic>structure elucidation</topic><topic>synthetic methods</topic><topic>Terphenyl Compounds - chemical synthesis</topic><topic>Terphenyl Compounds - chemistry</topic><topic>twistacene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xiao, Jinchong</creatorcontrib><creatorcontrib>Liu, Shuwei</creatorcontrib><creatorcontrib>Liu, Yi</creatorcontrib><creatorcontrib>Ji, Li</creatorcontrib><creatorcontrib>Liu, Xuewei</creatorcontrib><creatorcontrib>Zhang, Hua</creatorcontrib><creatorcontrib>Sun, Xiaowei</creatorcontrib><creatorcontrib>Zhang, Qichun</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xiao, Jinchong</au><au>Liu, Shuwei</au><au>Liu, Yi</au><au>Ji, Li</au><au>Liu, Xuewei</au><au>Zhang, Hua</au><au>Sun, Xiaowei</au><au>Zhang, Qichun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Structure, and Physical Properties of 5,7,14,16-Tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chemistry - An Asian Journal</addtitle><date>2012-03-05</date><risdate>2012</risdate><volume>7</volume><issue>3</issue><spage>561</spage><epage>564</epage><pages>561-564</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized through a retro‐Diels–Alder reaction. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The HOMO–LUMO gap of TBH calculated from the difference between the half‐wave redox potentials (E1/2ox=+0.40 eV and E1/2red=−1.78 eV) is 2.18 eV, which is in good agreement with the band gap (2.19 eV) derived from the UV/Vis absorption data. In addition, organic light‐emitting devices using TBH as emitter have been fabricated. The results revealed that TBH is a promising red light‐emitting candidate for applications in organic light‐emitting diodes.
There is a twist: A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The electrochemical characteristics of TBH and data of fabricated organic light‐emitting devices using TBH as emitter suggest that TBH is a promising red light‐emitting candidate for applications in organic light‐emitting diodes.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>22223424</pmid><doi>10.1002/asia.201100733</doi><tpages>4</tpages></addata></record> |
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| subjects | Chemistry Hydrocarbons, Aromatic - chemical synthesis Hydrocarbons, Aromatic - chemistry Models, Molecular Molecular Structure OLED semiconductors structure elucidation synthetic methods Terphenyl Compounds - chemical synthesis Terphenyl Compounds - chemistry twistacene |
| title | Synthesis, Structure, and Physical Properties of 5,7,14,16-Tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene |
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