A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles
A concise organolithium‐free route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective...
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| Veröffentlicht in: | European journal of organic chemistry 2018-05, Vol.2018 (19), p.2259-2266 |
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| container_title | European journal of organic chemistry |
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| creator | Baranov, Denis S. Uvarov, Mikhail N. Kazantsev, Maxim S. Glebov, Evgeni M. Nevostruev, Danil A. Mostovich, Evgeny A. Antonova, Olga V. Kulik, Leonid V. |
| description | A concise organolithium‐free route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron‐accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′‐[2,2′‐arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light‐induced electron transfer in their blend with a donor polymer, poly(3‐hexylthiophene‐2,5‐diyl), detected by electron paramagnetic resonance spectroscopy.
A three‐step sequence involving Sonogashira coupling, double thiophene annulation, and Knoevenagel condensation provides a concise and efficient route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers. |
| doi_str_mv | 10.1002/ejoc.201800275 |
| format | Article |
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A three‐step sequence involving Sonogashira coupling, double thiophene annulation, and Knoevenagel condensation provides a concise and efficient route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201800275</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Annulation ; Chemical reactions ; Construction standards ; Electron paramagnetic resonance ; Electron transfer ; Electrons ; Electron‐deficient compounds ; Fluorescence ; Functional organic materials ; Fused‐ring systems ; Molecular chains ; Organic chemistry ; Polycycles ; Quinones ; Sodium sulfide ; Spectrum analysis ; Substrates ; Sulfur heterocycles</subject><ispartof>European journal of organic chemistry, 2018-05, Vol.2018 (19), p.2259-2266</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3175-b59b40da0b798e62109422380d4febca5526b45c3398f805d3801e473572f1a23</citedby><cites>FETCH-LOGICAL-c3175-b59b40da0b798e62109422380d4febca5526b45c3398f805d3801e473572f1a23</cites><orcidid>0000-0002-0225-0455</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%2Fejoc.201800275$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201800275$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Baranov, Denis S.</creatorcontrib><creatorcontrib>Uvarov, Mikhail N.</creatorcontrib><creatorcontrib>Kazantsev, Maxim S.</creatorcontrib><creatorcontrib>Glebov, Evgeni M.</creatorcontrib><creatorcontrib>Nevostruev, Danil A.</creatorcontrib><creatorcontrib>Mostovich, Evgeny A.</creatorcontrib><creatorcontrib>Antonova, Olga V.</creatorcontrib><creatorcontrib>Kulik, Leonid V.</creatorcontrib><title>A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles</title><title>European journal of organic chemistry</title><description>A concise organolithium‐free route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron‐accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′‐[2,2′‐arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light‐induced electron transfer in their blend with a donor polymer, poly(3‐hexylthiophene‐2,5‐diyl), detected by electron paramagnetic resonance spectroscopy.
A three‐step sequence involving Sonogashira coupling, double thiophene annulation, and Knoevenagel condensation provides a concise and efficient route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers.</description><subject>Annulation</subject><subject>Chemical reactions</subject><subject>Construction standards</subject><subject>Electron paramagnetic resonance</subject><subject>Electron transfer</subject><subject>Electrons</subject><subject>Electron‐deficient compounds</subject><subject>Fluorescence</subject><subject>Functional organic materials</subject><subject>Fused‐ring systems</subject><subject>Molecular chains</subject><subject>Organic chemistry</subject><subject>Polycycles</subject><subject>Quinones</subject><subject>Sodium sulfide</subject><subject>Spectrum analysis</subject><subject>Substrates</subject><subject>Sulfur heterocycles</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFUE1LxDAQLaLgunr1XPCiYNckTT9yLEv9YmFBFIRlKWmaullqUpMs2tv-hL36N_xJ-0tMWdGjhyHzZt6byTzPO4VgBAFAV3yp2AgBmDqQRHveAAJCAhATsO9yHOIAkvD50DsyZgkAIHEMB95n5o-VZMJwn8rKz-taMMGl9R_UynLfKj9vOLNaye16kzHGWyvki48u0Xb95Uqz3yzTXPJKdE0pzDmErqI-FJV2oekM9qRNObcLodqF4zkUu-gaUTl0Ma9Eq1VL-wFSWC0abo69g5o2hp_8vEPv6Tp_HN8Gk-nN3TibBCyESRSUESkxqCgoE5LyGLmjMUJhCipc85LRKEJxiSMWhiStUxBVrgU5TsIoQTWkKBx6Z7u57gdvK25ssVQrLd3KAgEcYwIxjB1rtGMxrYzRvC5aLV6p7goIit7-ore_-LXfCchO8O6O6f5hF_n9dPyn_QYPKpI_</recordid><startdate>20180524</startdate><enddate>20180524</enddate><creator>Baranov, Denis S.</creator><creator>Uvarov, Mikhail N.</creator><creator>Kazantsev, Maxim S.</creator><creator>Glebov, Evgeni M.</creator><creator>Nevostruev, Danil A.</creator><creator>Mostovich, Evgeny A.</creator><creator>Antonova, Olga V.</creator><creator>Kulik, Leonid V.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-0225-0455</orcidid></search><sort><creationdate>20180524</creationdate><title>A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles</title><author>Baranov, Denis S. ; Uvarov, Mikhail N. ; Kazantsev, Maxim S. ; Glebov, Evgeni M. ; Nevostruev, Danil A. ; Mostovich, Evgeny A. ; Antonova, Olga V. ; Kulik, Leonid V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3175-b59b40da0b798e62109422380d4febca5526b45c3398f805d3801e473572f1a23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Annulation</topic><topic>Chemical reactions</topic><topic>Construction standards</topic><topic>Electron paramagnetic resonance</topic><topic>Electron transfer</topic><topic>Electrons</topic><topic>Electron‐deficient compounds</topic><topic>Fluorescence</topic><topic>Functional organic materials</topic><topic>Fused‐ring systems</topic><topic>Molecular chains</topic><topic>Organic chemistry</topic><topic>Polycycles</topic><topic>Quinones</topic><topic>Sodium sulfide</topic><topic>Spectrum analysis</topic><topic>Substrates</topic><topic>Sulfur heterocycles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Baranov, Denis S.</creatorcontrib><creatorcontrib>Uvarov, Mikhail N.</creatorcontrib><creatorcontrib>Kazantsev, Maxim S.</creatorcontrib><creatorcontrib>Glebov, Evgeni M.</creatorcontrib><creatorcontrib>Nevostruev, Danil A.</creatorcontrib><creatorcontrib>Mostovich, Evgeny A.</creatorcontrib><creatorcontrib>Antonova, Olga V.</creatorcontrib><creatorcontrib>Kulik, Leonid V.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Baranov, Denis S.</au><au>Uvarov, Mikhail N.</au><au>Kazantsev, Maxim S.</au><au>Glebov, Evgeni M.</au><au>Nevostruev, Danil A.</au><au>Mostovich, Evgeny A.</au><au>Antonova, Olga V.</au><au>Kulik, Leonid V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles</atitle><jtitle>European journal of organic chemistry</jtitle><date>2018-05-24</date><risdate>2018</risdate><volume>2018</volume><issue>19</issue><spage>2259</spage><epage>2266</epage><pages>2259-2266</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A concise organolithium‐free route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron‐accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′‐[2,2′‐arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light‐induced electron transfer in their blend with a donor polymer, poly(3‐hexylthiophene‐2,5‐diyl), detected by electron paramagnetic resonance spectroscopy.
A three‐step sequence involving Sonogashira coupling, double thiophene annulation, and Knoevenagel condensation provides a concise and efficient route to build electron‐accepting molecules consisting of two 2‐(11‐oxoanthra[1,2‐b]thiophen‐6‐ylidene)propanedinitrile units connected by functionalized π‐conjugated linkers.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201800275</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-0225-0455</orcidid></addata></record> |
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| subjects | Annulation Chemical reactions Construction standards Electron paramagnetic resonance Electron transfer Electrons Electron‐deficient compounds Fluorescence Functional organic materials Fused‐ring systems Molecular chains Organic chemistry Polycycles Quinones Sodium sulfide Spectrum analysis Substrates Sulfur heterocycles |
| title | A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles |
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