A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach
An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) via a thermally robust methoxyamine‐protecting group is demonstrated herein. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with metha...
Gespeichert in:
| Veröffentlicht in: | ChemSusChem 2020-05, Vol.13 (9), p.2386-2393 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2393 |
|---|---|
| container_issue | 9 |
| container_start_page | 2386 |
| container_title | ChemSusChem |
| container_volume | 13 |
| creator | Hansen, Kai‐Anders Chambers, Lewis C. Eing, Matthias Barner‐Kowollik, Christopher Fairfull‐Smith, Kathryn E. Blinco, James P. |
| description | An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) via a thermally robust methoxyamine‐protecting group is demonstrated herein. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). The polymerization of MTMA to poly(MTMA) (PMTMA) is investigated via free radical polymerization and reversible addition–fragmentation chain‐transfer polymerization (RAFT), a reversible‐deactivation radical polymerization technique. Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid (mCPBA) releases the electroactive PTMA. The redox activity of PTMA was confirmed by cyclic voltammetry in lithium‐ion coin cells.
Radical move: Protect! An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) is demonstrated. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid gives the desired PTMA. |
| doi_str_mv | 10.1002/cssc.201903529 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2381843622</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2398448684</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4509-2615f7131c47dfad2cb70f8c434ead8daeca18bb909594bbd91a818925c5a3ba3</originalsourceid><addsrcrecordid>eNqF0LtOwzAUBmALgSgUVkZkiYWlxbek9hgqKEggEBeJLTpxHHCVJsVOgG59BAaekCfBVaFILEzHlj7_tn-E9ijpU0LYkfZe9xmhivCIqTW0RWUselEsHtZXa047aNv7MSExUXG8iTqcMcK4HGwhSPClaZ7qtxlMbGU-5-_Xrm6Mbmz1iEeubqe4qB2-co9QWY1vILcaSnwMTWPcDF9CGBZK_zn_SCqclGFbQWNfDE6mU1eDftpBG0UAZvd7dtH96cnd8Kx3cTU6HyYXPS0ionosplExoJxqMcgLyJnOBqSQWnBhIJc5GA1UZpkiKlIiy3JFQVKpWKQj4BnwLjpc5oZrn1vjm3RivTZlCZWpW5-G_1IpeMxYoAd_6Lhuw7vLhVJSCBkH2UX9pdKu9t6ZIp06OwE3SylJF-Wni_LTVfnhwP53bJtNTL7iP20HoJbg1ZZm9k9cOry9Hf6GfwGQ0ZNl</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2398448684</pqid></control><display><type>article</type><title>A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach</title><source>Wiley Online Library Journals</source><creator>Hansen, Kai‐Anders ; Chambers, Lewis C. ; Eing, Matthias ; Barner‐Kowollik, Christopher ; Fairfull‐Smith, Kathryn E. ; Blinco, James P.</creator><creatorcontrib>Hansen, Kai‐Anders ; Chambers, Lewis C. ; Eing, Matthias ; Barner‐Kowollik, Christopher ; Fairfull‐Smith, Kathryn E. ; Blinco, James P.</creatorcontrib><description>An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) via a thermally robust methoxyamine‐protecting group is demonstrated herein. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). The polymerization of MTMA to poly(MTMA) (PMTMA) is investigated via free radical polymerization and reversible addition–fragmentation chain‐transfer polymerization (RAFT), a reversible‐deactivation radical polymerization technique. Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid (mCPBA) releases the electroactive PTMA. The redox activity of PTMA was confirmed by cyclic voltammetry in lithium‐ion coin cells.
Radical move: Protect! An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) is demonstrated. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid gives the desired PTMA.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.201903529</identifier><identifier>PMID: 32202387</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Addition polymerization ; cathode ; Deactivation ; Esterification ; Free radical polymerization ; Free radicals ; Lithium ; organic batteries ; Polymerization ; polymers ; radicals</subject><ispartof>ChemSusChem, 2020-05, Vol.13 (9), p.2386-2393</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4509-2615f7131c47dfad2cb70f8c434ead8daeca18bb909594bbd91a818925c5a3ba3</citedby><cites>FETCH-LOGICAL-c4509-2615f7131c47dfad2cb70f8c434ead8daeca18bb909594bbd91a818925c5a3ba3</cites><orcidid>0000-0003-0092-2040</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%2Fcssc.201903529$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcssc.201903529$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32202387$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hansen, Kai‐Anders</creatorcontrib><creatorcontrib>Chambers, Lewis C.</creatorcontrib><creatorcontrib>Eing, Matthias</creatorcontrib><creatorcontrib>Barner‐Kowollik, Christopher</creatorcontrib><creatorcontrib>Fairfull‐Smith, Kathryn E.</creatorcontrib><creatorcontrib>Blinco, James P.</creatorcontrib><title>A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) via a thermally robust methoxyamine‐protecting group is demonstrated herein. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). The polymerization of MTMA to poly(MTMA) (PMTMA) is investigated via free radical polymerization and reversible addition–fragmentation chain‐transfer polymerization (RAFT), a reversible‐deactivation radical polymerization technique. Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid (mCPBA) releases the electroactive PTMA. The redox activity of PTMA was confirmed by cyclic voltammetry in lithium‐ion coin cells.
Radical move: Protect! An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) is demonstrated. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid gives the desired PTMA.</description><subject>Addition polymerization</subject><subject>cathode</subject><subject>Deactivation</subject><subject>Esterification</subject><subject>Free radical polymerization</subject><subject>Free radicals</subject><subject>Lithium</subject><subject>organic batteries</subject><subject>Polymerization</subject><subject>polymers</subject><subject>radicals</subject><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqF0LtOwzAUBmALgSgUVkZkiYWlxbek9hgqKEggEBeJLTpxHHCVJsVOgG59BAaekCfBVaFILEzHlj7_tn-E9ijpU0LYkfZe9xmhivCIqTW0RWUselEsHtZXa047aNv7MSExUXG8iTqcMcK4HGwhSPClaZ7qtxlMbGU-5-_Xrm6Mbmz1iEeubqe4qB2-co9QWY1vILcaSnwMTWPcDF9CGBZK_zn_SCqclGFbQWNfDE6mU1eDftpBG0UAZvd7dtH96cnd8Kx3cTU6HyYXPS0ionosplExoJxqMcgLyJnOBqSQWnBhIJc5GA1UZpkiKlIiy3JFQVKpWKQj4BnwLjpc5oZrn1vjm3RivTZlCZWpW5-G_1IpeMxYoAd_6Lhuw7vLhVJSCBkH2UX9pdKu9t6ZIp06OwE3SylJF-Wni_LTVfnhwP53bJtNTL7iP20HoJbg1ZZm9k9cOry9Hf6GfwGQ0ZNl</recordid><startdate>20200508</startdate><enddate>20200508</enddate><creator>Hansen, Kai‐Anders</creator><creator>Chambers, Lewis C.</creator><creator>Eing, Matthias</creator><creator>Barner‐Kowollik, Christopher</creator><creator>Fairfull‐Smith, Kathryn E.</creator><creator>Blinco, James P.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0092-2040</orcidid></search><sort><creationdate>20200508</creationdate><title>A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach</title><author>Hansen, Kai‐Anders ; Chambers, Lewis C. ; Eing, Matthias ; Barner‐Kowollik, Christopher ; Fairfull‐Smith, Kathryn E. ; Blinco, James P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4509-2615f7131c47dfad2cb70f8c434ead8daeca18bb909594bbd91a818925c5a3ba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Addition polymerization</topic><topic>cathode</topic><topic>Deactivation</topic><topic>Esterification</topic><topic>Free radical polymerization</topic><topic>Free radicals</topic><topic>Lithium</topic><topic>organic batteries</topic><topic>Polymerization</topic><topic>polymers</topic><topic>radicals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hansen, Kai‐Anders</creatorcontrib><creatorcontrib>Chambers, Lewis C.</creatorcontrib><creatorcontrib>Eing, Matthias</creatorcontrib><creatorcontrib>Barner‐Kowollik, Christopher</creatorcontrib><creatorcontrib>Fairfull‐Smith, Kathryn E.</creatorcontrib><creatorcontrib>Blinco, James P.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>ChemSusChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hansen, Kai‐Anders</au><au>Chambers, Lewis C.</au><au>Eing, Matthias</au><au>Barner‐Kowollik, Christopher</au><au>Fairfull‐Smith, Kathryn E.</au><au>Blinco, James P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach</atitle><jtitle>ChemSusChem</jtitle><addtitle>ChemSusChem</addtitle><date>2020-05-08</date><risdate>2020</risdate><volume>13</volume><issue>9</issue><spage>2386</spage><epage>2393</epage><pages>2386-2393</pages><issn>1864-5631</issn><eissn>1864-564X</eissn><abstract>An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) via a thermally robust methoxyamine‐protecting group is demonstrated herein. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). The polymerization of MTMA to poly(MTMA) (PMTMA) is investigated via free radical polymerization and reversible addition–fragmentation chain‐transfer polymerization (RAFT), a reversible‐deactivation radical polymerization technique. Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid (mCPBA) releases the electroactive PTMA. The redox activity of PTMA was confirmed by cyclic voltammetry in lithium‐ion coin cells.
Radical move: Protect! An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) is demonstrated. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid gives the desired PTMA.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>32202387</pmid><doi>10.1002/cssc.201903529</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-0092-2040</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1864-5631 |
| ispartof | ChemSusChem, 2020-05, Vol.13 (9), p.2386-2393 |
| issn | 1864-5631 1864-564X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2381843622 |
| source | Wiley Online Library Journals |
| subjects | Addition polymerization cathode Deactivation Esterification Free radical polymerization Free radicals Lithium organic batteries Polymerization polymers radicals |
| title | A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-14T18%3A14%3A33IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Methoxyamine%E2%80%90Protecting%20Group%20for%20Organic%20Radical%20Battery%20Materials%E2%80%94An%20Alternative%20Approach&rft.jtitle=ChemSusChem&rft.au=Hansen,%20Kai%E2%80%90Anders&rft.date=2020-05-08&rft.volume=13&rft.issue=9&rft.spage=2386&rft.epage=2393&rft.pages=2386-2393&rft.issn=1864-5631&rft.eissn=1864-564X&rft_id=info:doi/10.1002/cssc.201903529&rft_dat=%3Cproquest_cross%3E2398448684%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2398448684&rft_id=info:pmid/32202387&rfr_iscdi=true |