Zwitterionic Ring Opening Polymerization with Isothioureas
Bicyclic isothioureas 1 and 2 mediate controlled ring opening polymerizations (ROP) of lactides in the absence of protic initiators to afford high molecular weight polylactides (PLA) with narrow polydispersities. The cyclic structure of the resulting PLA was determined by dilute solution viscosity m...
Gespeichert in:
| Veröffentlicht in: | ACS macro letters 2014-10, Vol.3 (10), p.1024-1028 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1028 |
|---|---|
| container_issue | 10 |
| container_start_page | 1024 |
| container_title | ACS macro letters |
| container_volume | 3 |
| creator | Zhang, Xiangyi Waymouth, Robert M |
| description | Bicyclic isothioureas 1 and 2 mediate controlled ring opening polymerizations (ROP) of lactides in the absence of protic initiators to afford high molecular weight polylactides (PLA) with narrow polydispersities. The cyclic structure of the resulting PLA was determined by dilute solution viscosity measurement and MALDI-TOF mass spectrometry. Compared to DBU initiator, isothioureas are more selective for producing cyclic PLA without appreciable linear contaminants. Mechanistic studies involving acyl amidinium support our hypothesis that DBU-initiated ZROP generates linear chains from a ketene aminal intermediate. |
| doi_str_mv | 10.1021/mz500525n |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2669503959</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2669503959</sourcerecordid><originalsourceid>FETCH-LOGICAL-a350t-e201ef93762908ed2a026a67b20654b685e224b41815a3dc34435052d86374753</originalsourceid><addsrcrecordid>eNptkEtLw0AUhQdRbKld-AckG0EX0XkncSfFR6FQEd24GSbJrZ2SZOpMgrS_3impxYV3cw_c7x44B6Fzgm8IpuS23gqMBRXNERpSIklMpGDHf_QAjb1f4TBCkjTjp2jAgsJJKofo7uPbtC04YxtTRK-m-Yzma2h2-8VWmzpctroN1yhwy2jqbbs0tnOg_Rk6WejKw3i_R-j98eFt8hzP5k_Tyf0s1kzgNgaKCSwylkia4RRKqjGVWiY5xVLwXKYCKOU5JykRmpUF4zz8CVqmkiU8EWyErnrftbNfHfhW1cYXUFW6Adt5RaXMBGaZyAJ63aOFs947WKi1M7V2G0Ww2rWlDm0F9mJv2-U1lAfyt5sAXPaALrxahcxNSPmP0Q-xZW6r</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2669503959</pqid></control><display><type>article</type><title>Zwitterionic Ring Opening Polymerization with Isothioureas</title><source>American Chemical Society Journals</source><creator>Zhang, Xiangyi ; Waymouth, Robert M</creator><creatorcontrib>Zhang, Xiangyi ; Waymouth, Robert M</creatorcontrib><description>Bicyclic isothioureas 1 and 2 mediate controlled ring opening polymerizations (ROP) of lactides in the absence of protic initiators to afford high molecular weight polylactides (PLA) with narrow polydispersities. The cyclic structure of the resulting PLA was determined by dilute solution viscosity measurement and MALDI-TOF mass spectrometry. Compared to DBU initiator, isothioureas are more selective for producing cyclic PLA without appreciable linear contaminants. Mechanistic studies involving acyl amidinium support our hypothesis that DBU-initiated ZROP generates linear chains from a ketene aminal intermediate.</description><identifier>ISSN: 2161-1653</identifier><identifier>EISSN: 2161-1653</identifier><identifier>DOI: 10.1021/mz500525n</identifier><identifier>PMID: 35610786</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>ACS macro letters, 2014-10, Vol.3 (10), p.1024-1028</ispartof><rights>Copyright © 2014 American Chemical Society</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a350t-e201ef93762908ed2a026a67b20654b685e224b41815a3dc34435052d86374753</citedby><cites>FETCH-LOGICAL-a350t-e201ef93762908ed2a026a67b20654b685e224b41815a3dc34435052d86374753</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/mz500525n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/mz500525n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35610786$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Xiangyi</creatorcontrib><creatorcontrib>Waymouth, Robert M</creatorcontrib><title>Zwitterionic Ring Opening Polymerization with Isothioureas</title><title>ACS macro letters</title><addtitle>ACS Macro Lett</addtitle><description>Bicyclic isothioureas 1 and 2 mediate controlled ring opening polymerizations (ROP) of lactides in the absence of protic initiators to afford high molecular weight polylactides (PLA) with narrow polydispersities. The cyclic structure of the resulting PLA was determined by dilute solution viscosity measurement and MALDI-TOF mass spectrometry. Compared to DBU initiator, isothioureas are more selective for producing cyclic PLA without appreciable linear contaminants. Mechanistic studies involving acyl amidinium support our hypothesis that DBU-initiated ZROP generates linear chains from a ketene aminal intermediate.</description><issn>2161-1653</issn><issn>2161-1653</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNptkEtLw0AUhQdRbKld-AckG0EX0XkncSfFR6FQEd24GSbJrZ2SZOpMgrS_3impxYV3cw_c7x44B6Fzgm8IpuS23gqMBRXNERpSIklMpGDHf_QAjb1f4TBCkjTjp2jAgsJJKofo7uPbtC04YxtTRK-m-Yzma2h2-8VWmzpctroN1yhwy2jqbbs0tnOg_Rk6WejKw3i_R-j98eFt8hzP5k_Tyf0s1kzgNgaKCSwylkia4RRKqjGVWiY5xVLwXKYCKOU5JykRmpUF4zz8CVqmkiU8EWyErnrftbNfHfhW1cYXUFW6Adt5RaXMBGaZyAJ63aOFs947WKi1M7V2G0Ww2rWlDm0F9mJv2-U1lAfyt5sAXPaALrxahcxNSPmP0Q-xZW6r</recordid><startdate>20141021</startdate><enddate>20141021</enddate><creator>Zhang, Xiangyi</creator><creator>Waymouth, Robert M</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20141021</creationdate><title>Zwitterionic Ring Opening Polymerization with Isothioureas</title><author>Zhang, Xiangyi ; Waymouth, Robert M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a350t-e201ef93762908ed2a026a67b20654b685e224b41815a3dc34435052d86374753</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xiangyi</creatorcontrib><creatorcontrib>Waymouth, Robert M</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>ACS macro letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Xiangyi</au><au>Waymouth, Robert M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Zwitterionic Ring Opening Polymerization with Isothioureas</atitle><jtitle>ACS macro letters</jtitle><addtitle>ACS Macro Lett</addtitle><date>2014-10-21</date><risdate>2014</risdate><volume>3</volume><issue>10</issue><spage>1024</spage><epage>1028</epage><pages>1024-1028</pages><issn>2161-1653</issn><eissn>2161-1653</eissn><abstract>Bicyclic isothioureas 1 and 2 mediate controlled ring opening polymerizations (ROP) of lactides in the absence of protic initiators to afford high molecular weight polylactides (PLA) with narrow polydispersities. The cyclic structure of the resulting PLA was determined by dilute solution viscosity measurement and MALDI-TOF mass spectrometry. Compared to DBU initiator, isothioureas are more selective for producing cyclic PLA without appreciable linear contaminants. Mechanistic studies involving acyl amidinium support our hypothesis that DBU-initiated ZROP generates linear chains from a ketene aminal intermediate.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>35610786</pmid><doi>10.1021/mz500525n</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2161-1653 |
| ispartof | ACS macro letters, 2014-10, Vol.3 (10), p.1024-1028 |
| issn | 2161-1653 2161-1653 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2669503959 |
| source | American Chemical Society Journals |
| title | Zwitterionic Ring Opening Polymerization with Isothioureas |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T18%3A38%3A36IST&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=Zwitterionic%20Ring%20Opening%20Polymerization%20with%20Isothioureas&rft.jtitle=ACS%20macro%20letters&rft.au=Zhang,%20Xiangyi&rft.date=2014-10-21&rft.volume=3&rft.issue=10&rft.spage=1024&rft.epage=1028&rft.pages=1024-1028&rft.issn=2161-1653&rft.eissn=2161-1653&rft_id=info:doi/10.1021/mz500525n&rft_dat=%3Cproquest_cross%3E2669503959%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=2669503959&rft_id=info:pmid/35610786&rfr_iscdi=true |