Syntheses and Crystal Structures of Fused Thiophenes: [7]Helicene and Double Helicene, a D2-Symmetric Dimer of 3,3′-Bis(dithieno[2,3-b:3′,2′-d]thiophene)
The efficient synthesis of (TMS)2-[7]helicene (rac-3) and double helicene, a D2-symmetric dimer of 3,3′-bis(dithieno[2,3-b:3′,2′-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular π-π interactions and S···S interactions. UV/vis spectra reveal that b...
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| Veröffentlicht in: | Journal of organic chemistry 2009-01, Vol.74 (1), p.408-411 |
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| container_title | Journal of organic chemistry |
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| creator | Li, Chunli Shi, Jianwu Xu, Li Wang, Yangguang Cheng, Yanxiang Wang, Hua |
| description | The efficient synthesis of (TMS)2-[7]helicene (rac-3) and double helicene, a D2-symmetric dimer of 3,3′-bis(dithieno[2,3-b:3′,2′-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular π-π interactions and S···S interactions. UV/vis spectra reveal that both 3 and 4 show significant π-electron delocalization. |
| doi_str_mv | 10.1021/jo802080g |
| format | Article |
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Org. Chem</addtitle><description>The efficient synthesis of (TMS)2-[7]helicene (rac-3) and double helicene, a D2-symmetric dimer of 3,3′-bis(dithieno[2,3-b:3′,2′-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular π-π interactions and S···S interactions. UV/vis spectra reveal that both 3 and 4 show significant π-electron delocalization.</description><subject>Chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Dimerization</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Polycyclic Compounds - chemical synthesis</subject><subject>Polycyclic Compounds - chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Thiophenes - chemical synthesis</subject><subject>Thiophenes - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkc2OEzEMxyMEYsvCgRdAuYBA6oCTTJLO3qBlWaSVOHQ5rVajJOPQVPNRksyhN96Ed-CReBKm0C6-WP77Z1u2CXnO4C0Dzt5thwVwWMC3B2TGJIdCVVA-JDMAzgvBlTgjT1LawmRSysfkjFUghayqGfm53vd5gwkTNX1Dl3GfsmnpOsfR5TFO8uDp5ZiwoTebMOw22GO6oLf67grb4Kbob91qGG2L9KTNqaErXqz3XYc5BkdXocN4aCXm4vePX8WHkF43IW8C9sMtn4vCXhz0OT8km7t8GvXmKXnkTZvw2dGfk6-XH2-WV8X1l0-fl--vC8Ml5KIRZSMrV5ZghVZca19ajUor76W1IJ32SgtmLLDSSzVBTliOxnMoHUohzsmrf313cfg-Ysp1F5LDtjU9DmOqldILplg5gS-O4Gg7bOpdDJ2J-_p00gl4eQRMcqb10fQupHuOw8RoEP8541K9HcbYT_vVDOrDS-v7l4o_I96SQg</recordid><startdate>20090102</startdate><enddate>20090102</enddate><creator>Li, Chunli</creator><creator>Shi, Jianwu</creator><creator>Xu, Li</creator><creator>Wang, Yangguang</creator><creator>Cheng, Yanxiang</creator><creator>Wang, Hua</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20090102</creationdate><title>Syntheses and Crystal Structures of Fused Thiophenes: [7]Helicene and Double Helicene, a D2-Symmetric Dimer of 3,3′-Bis(dithieno[2,3-b:3′,2′-d]thiophene)</title><author>Li, Chunli ; Shi, Jianwu ; Xu, Li ; Wang, Yangguang ; Cheng, Yanxiang ; Wang, Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a250t-d34d59c440b376277f4b7e676ff5bb05c7f6731ab014f56b37c3b2eaf204ce533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Dimerization</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Polycyclic Compounds - chemical synthesis</topic><topic>Polycyclic Compounds - chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Thiophenes - chemical synthesis</topic><topic>Thiophenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Chunli</creatorcontrib><creatorcontrib>Shi, Jianwu</creatorcontrib><creatorcontrib>Xu, Li</creatorcontrib><creatorcontrib>Wang, Yangguang</creatorcontrib><creatorcontrib>Cheng, Yanxiang</creatorcontrib><creatorcontrib>Wang, Hua</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Chunli</au><au>Shi, Jianwu</au><au>Xu, Li</au><au>Wang, Yangguang</au><au>Cheng, Yanxiang</au><au>Wang, Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and Crystal Structures of Fused Thiophenes: [7]Helicene and Double Helicene, a D2-Symmetric Dimer of 3,3′-Bis(dithieno[2,3-b:3′,2′-d]thiophene)</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-01-02</date><risdate>2009</risdate><volume>74</volume><issue>1</issue><spage>408</spage><epage>411</epage><pages>408-411</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The efficient synthesis of (TMS)2-[7]helicene (rac-3) and double helicene, a D2-symmetric dimer of 3,3′-bis(dithieno[2,3-b:3′,2′-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular π-π interactions and S···S interactions. UV/vis spectra reveal that both 3 and 4 show significant π-electron delocalization.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19053599</pmid><doi>10.1021/jo802080g</doi><tpages>4</tpages></addata></record> |
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| subjects | Chemistry Crystallography, X-Ray Dimerization Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Models, Molecular Molecular Structure Organic chemistry Polycyclic Compounds - chemical synthesis Polycyclic Compounds - chemistry Preparations and properties Stereoisomerism Thiophenes - chemical synthesis Thiophenes - chemistry |
| title | Syntheses and Crystal Structures of Fused Thiophenes: [7]Helicene and Double Helicene, a D2-Symmetric Dimer of 3,3′-Bis(dithieno[2,3-b:3′,2′-d]thiophene) |
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