Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-b]thiophenes and Pentacenes
A comparative study of suitably functionalized, highly soluble tetraceno[2,3-b]thiophenes (1−3) and pentacenes (4−6) that show higher photoxidative stability than that of unfunctionalized corresponding acenes is reported. The absorption and emission of 1−3 (A max = 624−656 nm, λmax = 634−672 nm, ΦF...
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| Veröffentlicht in: | Journal of organic chemistry 2007-08, Vol.72 (17), p.6584-6587 |
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| container_end_page | 6587 |
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| container_issue | 17 |
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| container_title | Journal of organic chemistry |
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| creator | Palayangoda, Sujeewa S Mondal, Rajib Shah, Bipin K Neckers, Douglas C |
| description | A comparative study of suitably functionalized, highly soluble tetraceno[2,3-b]thiophenes (1−3) and pentacenes (4−6) that show higher photoxidative stability than that of unfunctionalized corresponding acenes is reported. The absorption and emission of 1−3 (A max = 624−656 nm, λmax = 634−672 nm, ΦF ≈ 10%) and 4−6 (A max = 672−704 nm, λmax = 682−718 nm, ΦF ≈ 10%) were found to be systematically red-shifted by the substitution in the order of the tert-butylethynyl < triisopropylsilylethynyl < phenylethynyl groups. The oxidation potentials of these compounds were similar (E 1/2 ≈ 0.70 V), except for 4, which showed lower oxidation potential (E 1/2 ≈ 0.63 V). |
| doi_str_mv | 10.1021/jo0710331 |
| format | Article |
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Org. Chem</addtitle><description>A comparative study of suitably functionalized, highly soluble tetraceno[2,3-b]thiophenes (1−3) and pentacenes (4−6) that show higher photoxidative stability than that of unfunctionalized corresponding acenes is reported. The absorption and emission of 1−3 (A max = 624−656 nm, λmax = 634−672 nm, ΦF ≈ 10%) and 4−6 (A max = 672−704 nm, λmax = 682−718 nm, ΦF ≈ 10%) were found to be systematically red-shifted by the substitution in the order of the tert-butylethynyl < triisopropylsilylethynyl < phenylethynyl groups. The oxidation potentials of these compounds were similar (E 1/2 ≈ 0.70 V), except for 4, which showed lower oxidation potential (E 1/2 ≈ 0.63 V).</description><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</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>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNptkN-LEzEQx4MoXq_64D8g-6Jw4Gp-bLK7j3Kopx7eQSsKKmGSTGzO7W5NsnL9793acn1xXgIzn_ky-RDyhNGXjHL26magNaNCsHtkxiSnpWppdZ_MKOW8FFyJE3Ka0g2dSkr5kJywWkkplJyR74ttn1eYQioGX1yEn6tuWyyGbjQdFtC74uo2OMjhD-76GXbtJeYIFvvhG38hSvMjr8KwWWGP6d_GNfZ5N8b0iDzw0CV8fHjn5PPbN8vzi_Ly6t3789eXJVRVnUugRkrHjW8aysB45mhdg_TALfeipg4aR03rpW-4EdA6obiFyiP1prXCiTl5vs_dxOH3iCnrdUgWuw56HMakVcMqVU0_npOzPWjjkFJErzcxrCFuNaN6p1LfqZzYp4fQ0azRHcmDuwl4dgAgWeh8hN6GdOTaSX_VqIkr91xIGW_v5hB_aVWLWurl9UJ_WqgPXwX9oj8ec8Gm6Z4x9pO7_xz4Fx7xlwE</recordid><startdate>20070817</startdate><enddate>20070817</enddate><creator>Palayangoda, Sujeewa S</creator><creator>Mondal, Rajib</creator><creator>Shah, Bipin K</creator><creator>Neckers, Douglas C</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20070817</creationdate><title>Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-b]thiophenes and Pentacenes</title><author>Palayangoda, Sujeewa S ; Mondal, Rajib ; Shah, Bipin K ; Neckers, Douglas C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-a0b55d2bf8801abf1d077a5fa2c2f370da8d0b9f5f82b3a9d362ca4fe0fb9c3d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</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>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Palayangoda, Sujeewa S</creatorcontrib><creatorcontrib>Mondal, Rajib</creatorcontrib><creatorcontrib>Shah, Bipin K</creatorcontrib><creatorcontrib>Neckers, Douglas C</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Palayangoda, Sujeewa S</au><au>Mondal, Rajib</au><au>Shah, Bipin K</au><au>Neckers, Douglas C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-b]thiophenes and Pentacenes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2007-08-17</date><risdate>2007</risdate><volume>72</volume><issue>17</issue><spage>6584</spage><epage>6587</epage><pages>6584-6587</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A comparative study of suitably functionalized, highly soluble tetraceno[2,3-b]thiophenes (1−3) and pentacenes (4−6) that show higher photoxidative stability than that of unfunctionalized corresponding acenes is reported. The absorption and emission of 1−3 (A max = 624−656 nm, λmax = 634−672 nm, ΦF ≈ 10%) and 4−6 (A max = 672−704 nm, λmax = 682−718 nm, ΦF ≈ 10%) were found to be systematically red-shifted by the substitution in the order of the tert-butylethynyl < triisopropylsilylethynyl < phenylethynyl groups. The oxidation potentials of these compounds were similar (E 1/2 ≈ 0.70 V), except for 4, which showed lower oxidation potential (E 1/2 ≈ 0.63 V).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17655365</pmid><doi>10.1021/jo0710331</doi><tpages>4</tpages></addata></record> |
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| subjects | Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-b]thiophenes and Pentacenes |
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