Synthesis and Characterization of Oxadisilole-Fused 9-Aminoacridines and 12-Aminobenzo[b]acridines
Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at room temperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical,...
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| Veröffentlicht in: | European journal of organic chemistry 2014-07, Vol.2014 (19), p.4170-4178 |
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| container_title | European journal of organic chemistry |
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| creator | Chen, Xuanming Zhang, Yajuan Chen, Yali Zhang, Jie Chen, Jingda Li, Minjie Cao, Weiguo Chen, Jie |
| description | Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at room temperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined. The oxadisilole‐fused 9‐aminoacridines show potential for use as blue emitters for OLED applications, because of their high fluorescence quantum yields and good thermal stabilities. The proposed mechanism was also studied. Theoretical calculations on the HOMO and LUMO values of these compounds were performned.
Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at roomtemperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined. |
| doi_str_mv | 10.1002/ejoc.201402361 |
| format | Article |
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Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at roomtemperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201402361</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Arynes ; Cyclization ; Fused-ring systems ; Nitrogen heterocycles ; Photophysics ; Silicon</subject><ispartof>European journal of organic chemistry, 2014-07, Vol.2014 (19), p.4170-4178</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4911-706ff0c835445f94a2126fa5e022f84f65d2b0ac6f07009eeb8199365e8722c33</citedby><cites>FETCH-LOGICAL-c4911-706ff0c835445f94a2126fa5e022f84f65d2b0ac6f07009eeb8199365e8722c33</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%2Fejoc.201402361$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201402361$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Chen, Xuanming</creatorcontrib><creatorcontrib>Zhang, Yajuan</creatorcontrib><creatorcontrib>Chen, Yali</creatorcontrib><creatorcontrib>Zhang, Jie</creatorcontrib><creatorcontrib>Chen, Jingda</creatorcontrib><creatorcontrib>Li, Minjie</creatorcontrib><creatorcontrib>Cao, Weiguo</creatorcontrib><creatorcontrib>Chen, Jie</creatorcontrib><title>Synthesis and Characterization of Oxadisilole-Fused 9-Aminoacridines and 12-Aminobenzo[b]acridines</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at room temperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined. The oxadisilole‐fused 9‐aminoacridines show potential for use as blue emitters for OLED applications, because of their high fluorescence quantum yields and good thermal stabilities. The proposed mechanism was also studied. Theoretical calculations on the HOMO and LUMO values of these compounds were performned.
Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at roomtemperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined.</description><subject>Arynes</subject><subject>Cyclization</subject><subject>Fused-ring systems</subject><subject>Nitrogen heterocycles</subject><subject>Photophysics</subject><subject>Silicon</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkMFPwjAUxhejiYhePS_xPHxtt2494gKoIXIQgcSYptvaUBwrtiMCf70jM8Sbp_fy3vd738vnebcIeggA38uVyXsYUAiYUHTmdRAwFgBlcN70IQkDxMji0rtybgUAjFLU8bLXfVUvpdPOF1Xhp0thRV5Lqw-i1qbyjfInO1Fop0tTymC4dbLwWdBf68qI3OpCV7JFEW6nmawO5j37OG2vvQslSidvfmvXexsOpuljMJ6MntL-OMhDhlAQA1UK8oREYRgpFgqMMFUikoCxSkJFowJnIHKqIG6-lzJLEGOERjKJMc4J6Xp37d2NNV9b6Wq-MltbNZYcRYSRBCXAGlWvVeXWOGel4hur18LuOQJ-zJEfc-SnHBuAtcC3LuX-HzUfPE_Sv2zQstrVcndihf3kNCZxxOcvI_7AFtMZSeZ8Rn4AmnqGEw</recordid><startdate>201407</startdate><enddate>201407</enddate><creator>Chen, Xuanming</creator><creator>Zhang, Yajuan</creator><creator>Chen, Yali</creator><creator>Zhang, Jie</creator><creator>Chen, Jingda</creator><creator>Li, Minjie</creator><creator>Cao, Weiguo</creator><creator>Chen, Jie</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201407</creationdate><title>Synthesis and Characterization of Oxadisilole-Fused 9-Aminoacridines and 12-Aminobenzo[b]acridines</title><author>Chen, Xuanming ; Zhang, Yajuan ; Chen, Yali ; Zhang, Jie ; Chen, Jingda ; Li, Minjie ; Cao, Weiguo ; Chen, Jie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4911-706ff0c835445f94a2126fa5e022f84f65d2b0ac6f07009eeb8199365e8722c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Arynes</topic><topic>Cyclization</topic><topic>Fused-ring systems</topic><topic>Nitrogen heterocycles</topic><topic>Photophysics</topic><topic>Silicon</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Xuanming</creatorcontrib><creatorcontrib>Zhang, Yajuan</creatorcontrib><creatorcontrib>Chen, Yali</creatorcontrib><creatorcontrib>Zhang, Jie</creatorcontrib><creatorcontrib>Chen, Jingda</creatorcontrib><creatorcontrib>Li, Minjie</creatorcontrib><creatorcontrib>Cao, Weiguo</creatorcontrib><creatorcontrib>Chen, Jie</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Xuanming</au><au>Zhang, Yajuan</au><au>Chen, Yali</au><au>Zhang, Jie</au><au>Chen, Jingda</au><au>Li, Minjie</au><au>Cao, Weiguo</au><au>Chen, Jie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of Oxadisilole-Fused 9-Aminoacridines and 12-Aminobenzo[b]acridines</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2014-07</date><risdate>2014</risdate><volume>2014</volume><issue>19</issue><spage>4170</spage><epage>4178</epage><pages>4170-4178</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at room temperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined. The oxadisilole‐fused 9‐aminoacridines show potential for use as blue emitters for OLED applications, because of their high fluorescence quantum yields and good thermal stabilities. The proposed mechanism was also studied. Theoretical calculations on the HOMO and LUMO values of these compounds were performned.
Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at roomtemperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201402361</doi><tpages>9</tpages></addata></record> |
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| subjects | Arynes Cyclization Fused-ring systems Nitrogen heterocycles Photophysics Silicon |
| title | Synthesis and Characterization of Oxadisilole-Fused 9-Aminoacridines and 12-Aminobenzo[b]acridines |
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