Thiol-Michael coupling and ring-opening metathesis polymerization: facile access to functional exo-7-oxanorbornene dendron macromonomers
Thiol‐Michael Coupling and ROMP: Facile Access to Functional exo‐7‐Oxanorbornene Dendron Macromonomers Nucleophile‐mediated thiol‐Michael coupling is employed to prepare a small library of functional thioether‐based dendron monomers from novel di‐ and tetra‐acrylate functional ring‐opening metathesi...
Gespeichert in:
| Veröffentlicht in: | Polymer international 2014-07, Vol.63 (7), p.1174-1183 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1183 |
|---|---|
| container_issue | 7 |
| container_start_page | 1174 |
| container_title | Polymer international |
| container_volume | 63 |
| creator | Liu, Meina Burford, Robert P. Lowe, Andrew B. |
| description | Thiol‐Michael Coupling and ROMP: Facile Access to Functional exo‐7‐Oxanorbornene Dendron Macromonomers
Nucleophile‐mediated thiol‐Michael coupling is employed to prepare a small library of functional thioether‐based dendron monomers from novel di‐ and tetra‐acrylate functional ring‐opening metathesis polymerization (ROMP)‐active exo‐7‐oxanorbornene‐based monomers. The ROMP (co)polymerization of these novel monomers is evaluated with Grubbs 1st and 3rd generation initators.
This paper describes the synthesis of the 2‐ and 4‐functional acrylic exo‐7‐oxanorbornene species 2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl diacrylate and (((2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl)bis(oxy))bis(carbonyl))bis(2‐methylpropane‐2,1,3‐triyl) tetraacrylate, and their use as common precursors for the preparation of a small library of dendronized thioether adducts via nucleophile‐mediated thiol‐Michael coupling chemistry. We subsequently demonstrate that the dendronized monomers can be (co)polymerized via ring‐opening metathesis polymerization employing Grubbs'‐type Ru‐based initiators to give novel functional dendronized (co)polymers of predictable molecular weights and acceptable dispersities (ĐM = M‾ w/ M‾ n). © 2013 Society of Chemical Industry |
| doi_str_mv | 10.1002/pi.4664 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1551095456</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3325524521</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4604-ad5f6dad80c3233f770ee706c3c5ef10cf708b7c34d438532f6d93e4fe546f253</originalsourceid><addsrcrecordid>eNp10VFrFDEQB_BFFDyr-BUCIgqSOrvZJLu-SdFroWoLFR9Dmp14qdlkTXbxzk_gxzbHHX0QfErI_PiTmamq5zWc1gDN28mdtkK0D6pVDb2kUDfiYbWCnve0q4E9rp7kfAcAXd_3q-rPzcZFTz85s9HoiYnL5F34TnQYSCoXGicM-4cRZz1vMLtMpuh3Iyb3W88uhnfEauM8Em0M5kzmSOwSzL6kPcFtpJLGrQ4x3cYUMCAZMAwpBjJqk-IYQyxh-Wn1yGqf8dnxPKm-fvxwc3ZOL7-sL87eX1LTCmipHrgVgx46MKxhzEoJiBKEYYajrcFYCd2tNKwdWtZx1hTdM2wt8lbYhrOT6vUhd0rx54J5VqPLBr3XAeOSVc15mRtvuSj0xT_0Li6pdLVXrBG96IAV9eqgSjM5J7RqSm7UaadqUPuNqMmp_UaKfHnM09lob5MOxuV73pTv8lrI4t4c3K8y1t3_4tTVxTGVHrTLM27vtU4_VMmSXH37vFbN-lpenctrBewvaUOp6g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1532696803</pqid></control><display><type>article</type><title>Thiol-Michael coupling and ring-opening metathesis polymerization: facile access to functional exo-7-oxanorbornene dendron macromonomers</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Liu, Meina ; Burford, Robert P. ; Lowe, Andrew B.</creator><creatorcontrib>Liu, Meina ; Burford, Robert P. ; Lowe, Andrew B.</creatorcontrib><description>Thiol‐Michael Coupling and ROMP: Facile Access to Functional exo‐7‐Oxanorbornene Dendron Macromonomers
Nucleophile‐mediated thiol‐Michael coupling is employed to prepare a small library of functional thioether‐based dendron monomers from novel di‐ and tetra‐acrylate functional ring‐opening metathesis polymerization (ROMP)‐active exo‐7‐oxanorbornene‐based monomers. The ROMP (co)polymerization of these novel monomers is evaluated with Grubbs 1st and 3rd generation initators.
This paper describes the synthesis of the 2‐ and 4‐functional acrylic exo‐7‐oxanorbornene species 2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl diacrylate and (((2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl)bis(oxy))bis(carbonyl))bis(2‐methylpropane‐2,1,3‐triyl) tetraacrylate, and their use as common precursors for the preparation of a small library of dendronized thioether adducts via nucleophile‐mediated thiol‐Michael coupling chemistry. We subsequently demonstrate that the dendronized monomers can be (co)polymerized via ring‐opening metathesis polymerization employing Grubbs'‐type Ru‐based initiators to give novel functional dendronized (co)polymers of predictable molecular weights and acceptable dispersities (ĐM = M‾ w/ M‾ n). © 2013 Society of Chemical Industry</description><identifier>ISSN: 0959-8103</identifier><identifier>EISSN: 1097-0126</identifier><identifier>DOI: 10.1002/pi.4664</identifier><identifier>CODEN: PLYIEI</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Applied sciences ; Carbonyls ; click ; Coupling (molecular) ; Decomposition reactions ; dendronized polymers ; dendrons ; Exact sciences and technology ; Joining ; Libraries ; Metathesis ; Monomers ; Organic polymers ; Physicochemistry of polymers ; Polymerization ; Preparation, kinetics, thermodynamics, mechanism and catalysts ; ROMP ; thiol-Michael</subject><ispartof>Polymer international, 2014-07, Vol.63 (7), p.1174-1183</ispartof><rights>2013 Society of Chemical Industry</rights><rights>2015 INIST-CNRS</rights><rights>2014 Society of Chemical Industry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4604-ad5f6dad80c3233f770ee706c3c5ef10cf708b7c34d438532f6d93e4fe546f253</citedby><cites>FETCH-LOGICAL-c4604-ad5f6dad80c3233f770ee706c3c5ef10cf708b7c34d438532f6d93e4fe546f253</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpi.4664$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpi.4664$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=28535167$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Meina</creatorcontrib><creatorcontrib>Burford, Robert P.</creatorcontrib><creatorcontrib>Lowe, Andrew B.</creatorcontrib><title>Thiol-Michael coupling and ring-opening metathesis polymerization: facile access to functional exo-7-oxanorbornene dendron macromonomers</title><title>Polymer international</title><addtitle>Polym. Int</addtitle><description>Thiol‐Michael Coupling and ROMP: Facile Access to Functional exo‐7‐Oxanorbornene Dendron Macromonomers
Nucleophile‐mediated thiol‐Michael coupling is employed to prepare a small library of functional thioether‐based dendron monomers from novel di‐ and tetra‐acrylate functional ring‐opening metathesis polymerization (ROMP)‐active exo‐7‐oxanorbornene‐based monomers. The ROMP (co)polymerization of these novel monomers is evaluated with Grubbs 1st and 3rd generation initators.
This paper describes the synthesis of the 2‐ and 4‐functional acrylic exo‐7‐oxanorbornene species 2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl diacrylate and (((2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl)bis(oxy))bis(carbonyl))bis(2‐methylpropane‐2,1,3‐triyl) tetraacrylate, and their use as common precursors for the preparation of a small library of dendronized thioether adducts via nucleophile‐mediated thiol‐Michael coupling chemistry. We subsequently demonstrate that the dendronized monomers can be (co)polymerized via ring‐opening metathesis polymerization employing Grubbs'‐type Ru‐based initiators to give novel functional dendronized (co)polymers of predictable molecular weights and acceptable dispersities (ĐM = M‾ w/ M‾ n). © 2013 Society of Chemical Industry</description><subject>Applied sciences</subject><subject>Carbonyls</subject><subject>click</subject><subject>Coupling (molecular)</subject><subject>Decomposition reactions</subject><subject>dendronized polymers</subject><subject>dendrons</subject><subject>Exact sciences and technology</subject><subject>Joining</subject><subject>Libraries</subject><subject>Metathesis</subject><subject>Monomers</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Polymerization</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>ROMP</subject><subject>thiol-Michael</subject><issn>0959-8103</issn><issn>1097-0126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp10VFrFDEQB_BFFDyr-BUCIgqSOrvZJLu-SdFroWoLFR9Dmp14qdlkTXbxzk_gxzbHHX0QfErI_PiTmamq5zWc1gDN28mdtkK0D6pVDb2kUDfiYbWCnve0q4E9rp7kfAcAXd_3q-rPzcZFTz85s9HoiYnL5F34TnQYSCoXGicM-4cRZz1vMLtMpuh3Iyb3W88uhnfEauM8Em0M5kzmSOwSzL6kPcFtpJLGrQ4x3cYUMCAZMAwpBjJqk-IYQyxh-Wn1yGqf8dnxPKm-fvxwc3ZOL7-sL87eX1LTCmipHrgVgx46MKxhzEoJiBKEYYajrcFYCd2tNKwdWtZx1hTdM2wt8lbYhrOT6vUhd0rx54J5VqPLBr3XAeOSVc15mRtvuSj0xT_0Li6pdLVXrBG96IAV9eqgSjM5J7RqSm7UaadqUPuNqMmp_UaKfHnM09lob5MOxuV73pTv8lrI4t4c3K8y1t3_4tTVxTGVHrTLM27vtU4_VMmSXH37vFbN-lpenctrBewvaUOp6g</recordid><startdate>201407</startdate><enddate>201407</enddate><creator>Liu, Meina</creator><creator>Burford, Robert P.</creator><creator>Lowe, Andrew B.</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>F28</scope><scope>FR3</scope><scope>JG9</scope></search><sort><creationdate>201407</creationdate><title>Thiol-Michael coupling and ring-opening metathesis polymerization: facile access to functional exo-7-oxanorbornene dendron macromonomers</title><author>Liu, Meina ; Burford, Robert P. ; Lowe, Andrew B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4604-ad5f6dad80c3233f770ee706c3c5ef10cf708b7c34d438532f6d93e4fe546f253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Applied sciences</topic><topic>Carbonyls</topic><topic>click</topic><topic>Coupling (molecular)</topic><topic>Decomposition reactions</topic><topic>dendronized polymers</topic><topic>dendrons</topic><topic>Exact sciences and technology</topic><topic>Joining</topic><topic>Libraries</topic><topic>Metathesis</topic><topic>Monomers</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Polymerization</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>ROMP</topic><topic>thiol-Michael</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Meina</creatorcontrib><creatorcontrib>Burford, Robert P.</creatorcontrib><creatorcontrib>Lowe, Andrew B.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer international</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Meina</au><au>Burford, Robert P.</au><au>Lowe, Andrew B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiol-Michael coupling and ring-opening metathesis polymerization: facile access to functional exo-7-oxanorbornene dendron macromonomers</atitle><jtitle>Polymer international</jtitle><addtitle>Polym. Int</addtitle><date>2014-07</date><risdate>2014</risdate><volume>63</volume><issue>7</issue><spage>1174</spage><epage>1183</epage><pages>1174-1183</pages><issn>0959-8103</issn><eissn>1097-0126</eissn><coden>PLYIEI</coden><abstract>Thiol‐Michael Coupling and ROMP: Facile Access to Functional exo‐7‐Oxanorbornene Dendron Macromonomers
Nucleophile‐mediated thiol‐Michael coupling is employed to prepare a small library of functional thioether‐based dendron monomers from novel di‐ and tetra‐acrylate functional ring‐opening metathesis polymerization (ROMP)‐active exo‐7‐oxanorbornene‐based monomers. The ROMP (co)polymerization of these novel monomers is evaluated with Grubbs 1st and 3rd generation initators.
This paper describes the synthesis of the 2‐ and 4‐functional acrylic exo‐7‐oxanorbornene species 2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl diacrylate and (((2‐((2‐((3aR,7aS)‐1,3‐dioxo‐1,3,3a,4,7,7a‐hexahydro‐2H‐4,7‐epoxyisoindol‐2‐yl)ethoxy) carbonyl)‐2‐methylpropane‐1,3‐diyl)bis(oxy))bis(carbonyl))bis(2‐methylpropane‐2,1,3‐triyl) tetraacrylate, and their use as common precursors for the preparation of a small library of dendronized thioether adducts via nucleophile‐mediated thiol‐Michael coupling chemistry. We subsequently demonstrate that the dendronized monomers can be (co)polymerized via ring‐opening metathesis polymerization employing Grubbs'‐type Ru‐based initiators to give novel functional dendronized (co)polymers of predictable molecular weights and acceptable dispersities (ĐM = M‾ w/ M‾ n). © 2013 Society of Chemical Industry</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/pi.4664</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0959-8103 |
| ispartof | Polymer international, 2014-07, Vol.63 (7), p.1174-1183 |
| issn | 0959-8103 1097-0126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1551095456 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Applied sciences Carbonyls click Coupling (molecular) Decomposition reactions dendronized polymers dendrons Exact sciences and technology Joining Libraries Metathesis Monomers Organic polymers Physicochemistry of polymers Polymerization Preparation, kinetics, thermodynamics, mechanism and catalysts ROMP thiol-Michael |
| title | Thiol-Michael coupling and ring-opening metathesis polymerization: facile access to functional exo-7-oxanorbornene dendron macromonomers |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-27T01%3A40%3A24IST&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=Thiol-Michael%20coupling%20and%20ring-opening%20metathesis%20polymerization:%20facile%20access%20to%20functional%20exo-7-oxanorbornene%20dendron%20macromonomers&rft.jtitle=Polymer%20international&rft.au=Liu,%20Meina&rft.date=2014-07&rft.volume=63&rft.issue=7&rft.spage=1174&rft.epage=1183&rft.pages=1174-1183&rft.issn=0959-8103&rft.eissn=1097-0126&rft.coden=PLYIEI&rft_id=info:doi/10.1002/pi.4664&rft_dat=%3Cproquest_cross%3E3325524521%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=1532696803&rft_id=info:pmid/&rfr_iscdi=true |