Synthesis, structure, and electrochemistry of N-(3-thenoyl)fluorosulfonimide and bis(2-thenoic)imide. Preparation of polymers containing the fluorosulfonimide group
N-(3-Thenoyl)fluorosulfonimide, ( 1), C 4H 3SC(O)N(H)SO 2F, was prepared by the reaction of 3-thenoic acid with fluorosulfuryl isocyanate in acetonitrile solution. The new compound is a moderately strong nitrogen acid having a pK a of 2.4. Single-crystal X-ray structural analysis of ( 1) shows a pat...
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| Veröffentlicht in: | Synthetic metals 2009-08, Vol.159 (15), p.1628-1635 |
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| creator | MacNeill, Christopher M. Dai, Jian Day, Cynthia S. Lazar, Stephen P. Howell, S. Jarrett Noftle, Ronald E. |
| description | N-(3-Thenoyl)fluorosulfonimide, (
1), C
4H
3SC(O)N(H)SO
2F, was prepared by the reaction of 3-thenoic acid with fluorosulfuryl isocyanate in acetonitrile solution. The new compound is a moderately strong nitrogen acid having a pK
a of 2.4. Single-crystal X-ray structural analysis of (
1) shows a pattern of strong intermolecular hydrogen-bonding, resulting in the formation of linear chains. (
1) is electroinactive over a range of 2
V but undergoes hydrogen reduction (
E
p
/
2
c
=
−
0.28
V
). The salt of (
1) with TBA
+,
2, has been prepared and its crystal structure determined. The new dithienyl compound, bis(2-thienyl)imide,
3, has been prepared and crystallographically characterized. The polymers of
1,
3, and a polymer containing the fluorosulfonimide group formed from a copolymer of 3-methylthiophene/3-thiophene carboxylic acid are also reported. |
| doi_str_mv | 10.1016/j.synthmet.2009.04.028 |
| format | Article |
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1), C
4H
3SC(O)N(H)SO
2F, was prepared by the reaction of 3-thenoic acid with fluorosulfuryl isocyanate in acetonitrile solution. The new compound is a moderately strong nitrogen acid having a pK
a of 2.4. Single-crystal X-ray structural analysis of (
1) shows a pattern of strong intermolecular hydrogen-bonding, resulting in the formation of linear chains. (
1) is electroinactive over a range of 2
V but undergoes hydrogen reduction (
E
p
/
2
c
=
−
0.28
V
). The salt of (
1) with TBA
+,
2, has been prepared and its crystal structure determined. The new dithienyl compound, bis(2-thienyl)imide,
3, has been prepared and crystallographically characterized. The polymers of
1,
3, and a polymer containing the fluorosulfonimide group formed from a copolymer of 3-methylthiophene/3-thiophene carboxylic acid are also reported.</description><identifier>ISSN: 0379-6779</identifier><identifier>EISSN: 1879-3290</identifier><identifier>DOI: 10.1016/j.synthmet.2009.04.028</identifier><identifier>CODEN: SYMEDZ</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Applied sciences ; Crystal structure ; Cyclic voltammetry ; Exact sciences and technology ; Physicochemistry of polymers ; Polymerization ; Polymers and radiations ; Polythiophene ; Proton conductor ; Sulfonimide ; Sulfur heterocycle ; Thiopheneimide</subject><ispartof>Synthetic metals, 2009-08, Vol.159 (15), p.1628-1635</ispartof><rights>2009 Elsevier B.V.</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c373t-7682d34727878e651dae4cf1121061d91a5fe97a2487b2ca0995924ecc1c77aa3</citedby><cites>FETCH-LOGICAL-c373t-7682d34727878e651dae4cf1121061d91a5fe97a2487b2ca0995924ecc1c77aa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.synthmet.2009.04.028$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21879744$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>MacNeill, Christopher M.</creatorcontrib><creatorcontrib>Dai, Jian</creatorcontrib><creatorcontrib>Day, Cynthia S.</creatorcontrib><creatorcontrib>Lazar, Stephen P.</creatorcontrib><creatorcontrib>Howell, S. Jarrett</creatorcontrib><creatorcontrib>Noftle, Ronald E.</creatorcontrib><title>Synthesis, structure, and electrochemistry of N-(3-thenoyl)fluorosulfonimide and bis(2-thenoic)imide. Preparation of polymers containing the fluorosulfonimide group</title><title>Synthetic metals</title><description>N-(3-Thenoyl)fluorosulfonimide, (
1), C
4H
3SC(O)N(H)SO
2F, was prepared by the reaction of 3-thenoic acid with fluorosulfuryl isocyanate in acetonitrile solution. The new compound is a moderately strong nitrogen acid having a pK
a of 2.4. Single-crystal X-ray structural analysis of (
1) shows a pattern of strong intermolecular hydrogen-bonding, resulting in the formation of linear chains. (
1) is electroinactive over a range of 2
V but undergoes hydrogen reduction (
E
p
/
2
c
=
−
0.28
V
). The salt of (
1) with TBA
+,
2, has been prepared and its crystal structure determined. The new dithienyl compound, bis(2-thienyl)imide,
3, has been prepared and crystallographically characterized. The polymers of
1,
3, and a polymer containing the fluorosulfonimide group formed from a copolymer of 3-methylthiophene/3-thiophene carboxylic acid are also reported.</description><subject>Applied sciences</subject><subject>Crystal structure</subject><subject>Cyclic voltammetry</subject><subject>Exact sciences and technology</subject><subject>Physicochemistry of polymers</subject><subject>Polymerization</subject><subject>Polymers and radiations</subject><subject>Polythiophene</subject><subject>Proton conductor</subject><subject>Sulfonimide</subject><subject>Sulfur heterocycle</subject><subject>Thiopheneimide</subject><issn>0379-6779</issn><issn>1879-3290</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFkd9u1iAYh4lxiZ_TWzCcaLZkrUBpKWeaZZsmyzRRjwmjbze-UKhATXo_XujovumJBx5B4Pm9f_Ig9IaSmhLavd_XafX5foJcM0JkTXhNWP8M7WgvZNUwSZ6jHWnKvRNCvkAvU9oTQqhk7Q79_rZlIdl0hlOOi8lLhDOs_YDBgckxmHuYbPlacRjxTXXSVIX3YXWno1tCDGlxY_B2sgM8xm5tOmEHxprTx_caf40w66izDX4rMwe3ThATNsFnbb31d7gk8L8V72JY5lfoaNQuweun8xj9uLz4fv6puv5y9fn843VlGtHkSnQ9GxoumOhFD11LBw3cjJQySjo6SKrbEaTQjPfilhlNpGwl42AMNUJo3Ryjd4e6cww_F0hZlc0NOKc9hCWphveU8pYVsDuApkybIoxqjnbScVWUqE2K2qs_UtQmRRGuipQSfPvUQSej3Ri1Nzb9TbNNmeC8cB8OHJR1f1mIKhkL3sBgY7GihmD_1-oB5C6q4A</recordid><startdate>20090801</startdate><enddate>20090801</enddate><creator>MacNeill, Christopher M.</creator><creator>Dai, Jian</creator><creator>Day, Cynthia S.</creator><creator>Lazar, Stephen P.</creator><creator>Howell, S. Jarrett</creator><creator>Noftle, Ronald E.</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20090801</creationdate><title>Synthesis, structure, and electrochemistry of N-(3-thenoyl)fluorosulfonimide and bis(2-thenoic)imide. Preparation of polymers containing the fluorosulfonimide group</title><author>MacNeill, Christopher M. ; Dai, Jian ; Day, Cynthia S. ; Lazar, Stephen P. ; Howell, S. Jarrett ; Noftle, Ronald E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-7682d34727878e651dae4cf1121061d91a5fe97a2487b2ca0995924ecc1c77aa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Applied sciences</topic><topic>Crystal structure</topic><topic>Cyclic voltammetry</topic><topic>Exact sciences and technology</topic><topic>Physicochemistry of polymers</topic><topic>Polymerization</topic><topic>Polymers and radiations</topic><topic>Polythiophene</topic><topic>Proton conductor</topic><topic>Sulfonimide</topic><topic>Sulfur heterocycle</topic><topic>Thiopheneimide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>MacNeill, Christopher M.</creatorcontrib><creatorcontrib>Dai, Jian</creatorcontrib><creatorcontrib>Day, Cynthia S.</creatorcontrib><creatorcontrib>Lazar, Stephen P.</creatorcontrib><creatorcontrib>Howell, S. Jarrett</creatorcontrib><creatorcontrib>Noftle, Ronald E.</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Synthetic metals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>MacNeill, Christopher M.</au><au>Dai, Jian</au><au>Day, Cynthia S.</au><au>Lazar, Stephen P.</au><au>Howell, S. Jarrett</au><au>Noftle, Ronald E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, structure, and electrochemistry of N-(3-thenoyl)fluorosulfonimide and bis(2-thenoic)imide. Preparation of polymers containing the fluorosulfonimide group</atitle><jtitle>Synthetic metals</jtitle><date>2009-08-01</date><risdate>2009</risdate><volume>159</volume><issue>15</issue><spage>1628</spage><epage>1635</epage><pages>1628-1635</pages><issn>0379-6779</issn><eissn>1879-3290</eissn><coden>SYMEDZ</coden><abstract>N-(3-Thenoyl)fluorosulfonimide, (
1), C
4H
3SC(O)N(H)SO
2F, was prepared by the reaction of 3-thenoic acid with fluorosulfuryl isocyanate in acetonitrile solution. The new compound is a moderately strong nitrogen acid having a pK
a of 2.4. Single-crystal X-ray structural analysis of (
1) shows a pattern of strong intermolecular hydrogen-bonding, resulting in the formation of linear chains. (
1) is electroinactive over a range of 2
V but undergoes hydrogen reduction (
E
p
/
2
c
=
−
0.28
V
). The salt of (
1) with TBA
+,
2, has been prepared and its crystal structure determined. The new dithienyl compound, bis(2-thienyl)imide,
3, has been prepared and crystallographically characterized. The polymers of
1,
3, and a polymer containing the fluorosulfonimide group formed from a copolymer of 3-methylthiophene/3-thiophene carboxylic acid are also reported.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.synthmet.2009.04.028</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0379-6779 |
| ispartof | Synthetic metals, 2009-08, Vol.159 (15), p.1628-1635 |
| issn | 0379-6779 1879-3290 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_34811452 |
| source | Elsevier ScienceDirect Journals Complete |
| subjects | Applied sciences Crystal structure Cyclic voltammetry Exact sciences and technology Physicochemistry of polymers Polymerization Polymers and radiations Polythiophene Proton conductor Sulfonimide Sulfur heterocycle Thiopheneimide |
| title | Synthesis, structure, and electrochemistry of N-(3-thenoyl)fluorosulfonimide and bis(2-thenoic)imide. Preparation of polymers containing the fluorosulfonimide group |
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