Formamide based monomer for highly functionalized polymers
Multicomponent reactions (MCRs) are widely used in organic chemistry to simplify the synthesis of highly functionalized molecules in a single‐pot reaction. However, their utility for polymer post‐functionalization is severely limited due to the complexity of handling highly reactive and unpleasant i...
Gespeichert in:
| Veröffentlicht in: | Journal of polymer science (2020) 2022-01, Vol.60 (1), p.131-141 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 141 |
|---|---|
| container_issue | 1 |
| container_start_page | 131 |
| container_title | Journal of polymer science (2020) |
| container_volume | 60 |
| creator | Chen, Ri Ayyakkalai, Balamurugan Sun, Jian Lee, Gene A. Gopalan, Padma |
| description | Multicomponent reactions (MCRs) are widely used in organic chemistry to simplify the synthesis of highly functionalized molecules in a single‐pot reaction. However, their utility for polymer post‐functionalization is severely limited due to the complexity of handling highly reactive and unpleasant isocyanide compounds. In this work, we present a stable methacrylate monomer 2‐formamido ethyl methacrylate (FEMA) containing a benign formamide group that can be converted to isocyanide in situ and that can undergo MCRs in a one‐pot protocol. Block and random copolymers of FEMA with methyl methacrylate were tested for efficiency in MCRs. As a function of composition and architecture, MCR conversions of >90% was achieved in the polymers. This benign bench stable monomer allows incorporation of complex functionality in a one‐pot synthesis to the polymer sidechain using MCRs without direct handling of the isocyanide monomers and polymers. |
| doi_str_mv | 10.1002/pol.20210651 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2721315680</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2721315680</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3073-e11fe4ea061dc05ee93f57ff93aa141c8ec3702d1fcad5212c9c9aa51819492f3</originalsourceid><addsrcrecordid>eNp90EFLwzAUB_AgCo65mx-g4NXO95ImbbyN4VQYzIOeQ0wT19EuNVmR-umNTD16eu_w470_f0IuEeYIQG96384pUATB8YRMqChoXqCQp387h3Myi3EHiTMuChATcrvyodNdU9vsVUdbZ53f-86GzPmQbZu3bTtmbtibQ-P3um0-k0iPxiTiBTlzuo129jOn5GV197x8yNeb-8flYp0bBiXLLaKzhdUgsDbArZXM8dI5ybTGAk1lDSuB1uiMrjlFaqSRWnOsUBaSOjYlV8e7ffDvg40HtfNDSGmioiVFhlxUkNT1UZngYwzWqT40nQ6jQlDfBamUW_0WlDg78o-mteO_Vj1t1guWKmPsC-RGZ94</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2721315680</pqid></control><display><type>article</type><title>Formamide based monomer for highly functionalized polymers</title><source>Access via Wiley Online Library</source><creator>Chen, Ri ; Ayyakkalai, Balamurugan ; Sun, Jian ; Lee, Gene A. ; Gopalan, Padma</creator><creatorcontrib>Chen, Ri ; Ayyakkalai, Balamurugan ; Sun, Jian ; Lee, Gene A. ; Gopalan, Padma</creatorcontrib><description>Multicomponent reactions (MCRs) are widely used in organic chemistry to simplify the synthesis of highly functionalized molecules in a single‐pot reaction. However, their utility for polymer post‐functionalization is severely limited due to the complexity of handling highly reactive and unpleasant isocyanide compounds. In this work, we present a stable methacrylate monomer 2‐formamido ethyl methacrylate (FEMA) containing a benign formamide group that can be converted to isocyanide in situ and that can undergo MCRs in a one‐pot protocol. Block and random copolymers of FEMA with methyl methacrylate were tested for efficiency in MCRs. As a function of composition and architecture, MCR conversions of >90% was achieved in the polymers. This benign bench stable monomer allows incorporation of complex functionality in a one‐pot synthesis to the polymer sidechain using MCRs without direct handling of the isocyanide monomers and polymers.</description><identifier>ISSN: 2642-4150</identifier><identifier>EISSN: 2642-4169</identifier><identifier>DOI: 10.1002/pol.20210651</identifier><language>eng</language><publisher>Hoboken, USA: John Wiley & Sons, Inc</publisher><subject>Block copolymers ; Chemical synthesis ; Complexity ; Copolymers ; Monomers ; multicomponent reactions ; Organic chemistry ; peptide conjugation ; polymer post‐functionalization ; Polymers ; Polymethyl methacrylate</subject><ispartof>Journal of polymer science (2020), 2022-01, Vol.60 (1), p.131-141</ispartof><rights>2021 Wiley Periodicals LLC.</rights><rights>2022 Wiley Periodicals LLC.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3073-e11fe4ea061dc05ee93f57ff93aa141c8ec3702d1fcad5212c9c9aa51819492f3</citedby><cites>FETCH-LOGICAL-c3073-e11fe4ea061dc05ee93f57ff93aa141c8ec3702d1fcad5212c9c9aa51819492f3</cites><orcidid>0000-0002-1955-640X</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%2Fpol.20210651$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpol.20210651$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Chen, Ri</creatorcontrib><creatorcontrib>Ayyakkalai, Balamurugan</creatorcontrib><creatorcontrib>Sun, Jian</creatorcontrib><creatorcontrib>Lee, Gene A.</creatorcontrib><creatorcontrib>Gopalan, Padma</creatorcontrib><title>Formamide based monomer for highly functionalized polymers</title><title>Journal of polymer science (2020)</title><description>Multicomponent reactions (MCRs) are widely used in organic chemistry to simplify the synthesis of highly functionalized molecules in a single‐pot reaction. However, their utility for polymer post‐functionalization is severely limited due to the complexity of handling highly reactive and unpleasant isocyanide compounds. In this work, we present a stable methacrylate monomer 2‐formamido ethyl methacrylate (FEMA) containing a benign formamide group that can be converted to isocyanide in situ and that can undergo MCRs in a one‐pot protocol. Block and random copolymers of FEMA with methyl methacrylate were tested for efficiency in MCRs. As a function of composition and architecture, MCR conversions of >90% was achieved in the polymers. This benign bench stable monomer allows incorporation of complex functionality in a one‐pot synthesis to the polymer sidechain using MCRs without direct handling of the isocyanide monomers and polymers.</description><subject>Block copolymers</subject><subject>Chemical synthesis</subject><subject>Complexity</subject><subject>Copolymers</subject><subject>Monomers</subject><subject>multicomponent reactions</subject><subject>Organic chemistry</subject><subject>peptide conjugation</subject><subject>polymer post‐functionalization</subject><subject>Polymers</subject><subject>Polymethyl methacrylate</subject><issn>2642-4150</issn><issn>2642-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp90EFLwzAUB_AgCo65mx-g4NXO95ImbbyN4VQYzIOeQ0wT19EuNVmR-umNTD16eu_w470_f0IuEeYIQG96384pUATB8YRMqChoXqCQp387h3Myi3EHiTMuChATcrvyodNdU9vsVUdbZ53f-86GzPmQbZu3bTtmbtibQ-P3um0-k0iPxiTiBTlzuo129jOn5GV197x8yNeb-8flYp0bBiXLLaKzhdUgsDbArZXM8dI5ybTGAk1lDSuB1uiMrjlFaqSRWnOsUBaSOjYlV8e7ffDvg40HtfNDSGmioiVFhlxUkNT1UZngYwzWqT40nQ6jQlDfBamUW_0WlDg78o-mteO_Vj1t1guWKmPsC-RGZ94</recordid><startdate>20220101</startdate><enddate>20220101</enddate><creator>Chen, Ri</creator><creator>Ayyakkalai, Balamurugan</creator><creator>Sun, Jian</creator><creator>Lee, Gene A.</creator><creator>Gopalan, Padma</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-1955-640X</orcidid></search><sort><creationdate>20220101</creationdate><title>Formamide based monomer for highly functionalized polymers</title><author>Chen, Ri ; Ayyakkalai, Balamurugan ; Sun, Jian ; Lee, Gene A. ; Gopalan, Padma</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3073-e11fe4ea061dc05ee93f57ff93aa141c8ec3702d1fcad5212c9c9aa51819492f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Block copolymers</topic><topic>Chemical synthesis</topic><topic>Complexity</topic><topic>Copolymers</topic><topic>Monomers</topic><topic>multicomponent reactions</topic><topic>Organic chemistry</topic><topic>peptide conjugation</topic><topic>polymer post‐functionalization</topic><topic>Polymers</topic><topic>Polymethyl methacrylate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Ri</creatorcontrib><creatorcontrib>Ayyakkalai, Balamurugan</creatorcontrib><creatorcontrib>Sun, Jian</creatorcontrib><creatorcontrib>Lee, Gene A.</creatorcontrib><creatorcontrib>Gopalan, Padma</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of polymer science (2020)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Ri</au><au>Ayyakkalai, Balamurugan</au><au>Sun, Jian</au><au>Lee, Gene A.</au><au>Gopalan, Padma</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formamide based monomer for highly functionalized polymers</atitle><jtitle>Journal of polymer science (2020)</jtitle><date>2022-01-01</date><risdate>2022</risdate><volume>60</volume><issue>1</issue><spage>131</spage><epage>141</epage><pages>131-141</pages><issn>2642-4150</issn><eissn>2642-4169</eissn><abstract>Multicomponent reactions (MCRs) are widely used in organic chemistry to simplify the synthesis of highly functionalized molecules in a single‐pot reaction. However, their utility for polymer post‐functionalization is severely limited due to the complexity of handling highly reactive and unpleasant isocyanide compounds. In this work, we present a stable methacrylate monomer 2‐formamido ethyl methacrylate (FEMA) containing a benign formamide group that can be converted to isocyanide in situ and that can undergo MCRs in a one‐pot protocol. Block and random copolymers of FEMA with methyl methacrylate were tested for efficiency in MCRs. As a function of composition and architecture, MCR conversions of >90% was achieved in the polymers. This benign bench stable monomer allows incorporation of complex functionality in a one‐pot synthesis to the polymer sidechain using MCRs without direct handling of the isocyanide monomers and polymers.</abstract><cop>Hoboken, USA</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/pol.20210651</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-1955-640X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2642-4150 |
| ispartof | Journal of polymer science (2020), 2022-01, Vol.60 (1), p.131-141 |
| issn | 2642-4150 2642-4169 |
| language | eng |
| recordid | cdi_proquest_journals_2721315680 |
| source | Access via Wiley Online Library |
| subjects | Block copolymers Chemical synthesis Complexity Copolymers Monomers multicomponent reactions Organic chemistry peptide conjugation polymer post‐functionalization Polymers Polymethyl methacrylate |
| title | Formamide based monomer for highly functionalized polymers |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T11%3A55%3A05IST&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=Formamide%20based%20monomer%20for%20highly%20functionalized%20polymers&rft.jtitle=Journal%20of%20polymer%20science%20(2020)&rft.au=Chen,%20Ri&rft.date=2022-01-01&rft.volume=60&rft.issue=1&rft.spage=131&rft.epage=141&rft.pages=131-141&rft.issn=2642-4150&rft.eissn=2642-4169&rft_id=info:doi/10.1002/pol.20210651&rft_dat=%3Cproquest_cross%3E2721315680%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=2721315680&rft_id=info:pmid/&rfr_iscdi=true |