Quinoline-8-olato-chromium catalysts with pseudohalogen effects for the CO2/cyclohexene epoxide copolymerization
[Display omitted] Based on our previous studies utilizing CrIII catalysts with trifluoroacetate as labile ligand and an ansa-bis-quinoline-olato ligand as a chemically more robust variant compared to known salen-type N2O2 ligands, we synthesized and investigated a series of structurally similar quin...
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| Veröffentlicht in: | European polymer journal 2019-11, Vol.120, p.109245, Article 109245 |
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| creator | Hartweg, Manuel Sundermeyer, Jörg |
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Based on our previous studies utilizing CrIII catalysts with trifluoroacetate as labile ligand and an ansa-bis-quinoline-olato ligand as a chemically more robust variant compared to known salen-type N2O2 ligands, we synthesized and investigated a series of structurally similar quinoline-8-olato chromium complexes with different active (pseudo-)halogen ligands X in [(babhq)CrX], (babhq = 2,2′-(butyl-azanediyl)bis(quinolin-8-olate), X = Cl, NCO, and N3. We demonstrate a high activity of these CrIII complexes in the solvent free carbon dioxide/cyclohexene oxide (CHO) copolymerization compared to the state of the art. In much deeper detail than in our previous communication, we altered the labile ligand X and undertook a catalyst screening on the polymerization parameters, such as pressure, temperature, and cocatalyst, i.e. [PPN]N3 (bis(triphenylphosphine)iminiun azide). The activity of the chromium systems was found to much depend on the labile (pseudo-)halogen ligand X and increases in the order Cl |
| doi_str_mv | 10.1016/j.eurpolymj.2019.109245 |
| format | Article |
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Based on our previous studies utilizing CrIII catalysts with trifluoroacetate as labile ligand and an ansa-bis-quinoline-olato ligand as a chemically more robust variant compared to known salen-type N2O2 ligands, we synthesized and investigated a series of structurally similar quinoline-8-olato chromium complexes with different active (pseudo-)halogen ligands X in [(babhq)CrX], (babhq = 2,2′-(butyl-azanediyl)bis(quinolin-8-olate), X = Cl, NCO, and N3. We demonstrate a high activity of these CrIII complexes in the solvent free carbon dioxide/cyclohexene oxide (CHO) copolymerization compared to the state of the art. In much deeper detail than in our previous communication, we altered the labile ligand X and undertook a catalyst screening on the polymerization parameters, such as pressure, temperature, and cocatalyst, i.e. [PPN]N3 (bis(triphenylphosphine)iminiun azide). The activity of the chromium systems was found to much depend on the labile (pseudo-)halogen ligand X and increases in the order Cl < NCO < N3. Especially the azide complex [(babhq)CrN3] displays a high activity, displaying a TOF of 2165 h−1 after 1 h of reaction time along with an induction period of 30 min. At longer reaction times, up to 94% monomer conversion selectively into the respective polycarbonate (pCHC) is observed.</description><identifier>ISSN: 0014-3057</identifier><identifier>EISSN: 1873-1945</identifier><identifier>DOI: 10.1016/j.eurpolymj.2019.109245</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Carbon dioxide ; Catalysts ; Chromium ; Chromium catalysts ; CO2/epoxide copolymerization ; Copolymerization ; Cyclohexene ; Ligands ; Organic chemistry ; Polycarbonates ; Polymerization ; Polymerization catalysis ; Quinoline ; Reaction time ; Ring-opening polymerization ; Studies</subject><ispartof>European polymer journal, 2019-11, Vol.120, p.109245, Article 109245</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright Elsevier BV Nov 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c380t-d72ae357a90524131f77fe500d2a111c7ceb9dbadf5df27ed35c90e2aa2edd603</citedby><cites>FETCH-LOGICAL-c380t-d72ae357a90524131f77fe500d2a111c7ceb9dbadf5df27ed35c90e2aa2edd603</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0014305719316817$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids></links><search><creatorcontrib>Hartweg, Manuel</creatorcontrib><creatorcontrib>Sundermeyer, Jörg</creatorcontrib><title>Quinoline-8-olato-chromium catalysts with pseudohalogen effects for the CO2/cyclohexene epoxide copolymerization</title><title>European polymer journal</title><description>[Display omitted]
Based on our previous studies utilizing CrIII catalysts with trifluoroacetate as labile ligand and an ansa-bis-quinoline-olato ligand as a chemically more robust variant compared to known salen-type N2O2 ligands, we synthesized and investigated a series of structurally similar quinoline-8-olato chromium complexes with different active (pseudo-)halogen ligands X in [(babhq)CrX], (babhq = 2,2′-(butyl-azanediyl)bis(quinolin-8-olate), X = Cl, NCO, and N3. We demonstrate a high activity of these CrIII complexes in the solvent free carbon dioxide/cyclohexene oxide (CHO) copolymerization compared to the state of the art. In much deeper detail than in our previous communication, we altered the labile ligand X and undertook a catalyst screening on the polymerization parameters, such as pressure, temperature, and cocatalyst, i.e. [PPN]N3 (bis(triphenylphosphine)iminiun azide). The activity of the chromium systems was found to much depend on the labile (pseudo-)halogen ligand X and increases in the order Cl < NCO < N3. Especially the azide complex [(babhq)CrN3] displays a high activity, displaying a TOF of 2165 h−1 after 1 h of reaction time along with an induction period of 30 min. At longer reaction times, up to 94% monomer conversion selectively into the respective polycarbonate (pCHC) is observed.</description><subject>Carbon dioxide</subject><subject>Catalysts</subject><subject>Chromium</subject><subject>Chromium catalysts</subject><subject>CO2/epoxide copolymerization</subject><subject>Copolymerization</subject><subject>Cyclohexene</subject><subject>Ligands</subject><subject>Organic chemistry</subject><subject>Polycarbonates</subject><subject>Polymerization</subject><subject>Polymerization catalysis</subject><subject>Quinoline</subject><subject>Reaction time</subject><subject>Ring-opening polymerization</subject><subject>Studies</subject><issn>0014-3057</issn><issn>1873-1945</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOwzAQRS0EEqXwDVhindaPpE6WVcVLQqqQYG259pg4SuJgJ9Dw9aQUsWU10sy9d2YOQteULCihq2W1gCF0vh6basEILaZuwdLsBM1oLnhCizQ7RTNCaJpwkolzdBFjRQgRfMVnqHseXOtr10KSJ75WvU90GXzjhgZr1at6jH3En64vcRdhML5UtX-DFoO1oKeR9QH3JeDNli31qGtfwh5awND5vTOAtf-5DYL7Ur3z7SU6s6qOcPVb5-j17vZl85A8be8fN-unRPOc9IkRTAHPhCpIxlLKqRXCQkaIYYpSqoWGXWF2ytjMWCbA8EwXBJhSDIxZET5HN8fcLvj3AWIvKz-EdlopGWcTiZwV6aQSR5UOPsYAVnbBNSqMkhJ5wCsr-YdXHvDKI97JuT46YXriw0GQUTtoNRgXJjDSePdvxjcxN4ty</recordid><startdate>20191101</startdate><enddate>20191101</enddate><creator>Hartweg, Manuel</creator><creator>Sundermeyer, Jörg</creator><general>Elsevier Ltd</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20191101</creationdate><title>Quinoline-8-olato-chromium catalysts with pseudohalogen effects for the CO2/cyclohexene epoxide copolymerization</title><author>Hartweg, Manuel ; Sundermeyer, Jörg</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c380t-d72ae357a90524131f77fe500d2a111c7ceb9dbadf5df27ed35c90e2aa2edd603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Carbon dioxide</topic><topic>Catalysts</topic><topic>Chromium</topic><topic>Chromium catalysts</topic><topic>CO2/epoxide copolymerization</topic><topic>Copolymerization</topic><topic>Cyclohexene</topic><topic>Ligands</topic><topic>Organic chemistry</topic><topic>Polycarbonates</topic><topic>Polymerization</topic><topic>Polymerization catalysis</topic><topic>Quinoline</topic><topic>Reaction time</topic><topic>Ring-opening polymerization</topic><topic>Studies</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hartweg, Manuel</creatorcontrib><creatorcontrib>Sundermeyer, Jörg</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>European polymer journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hartweg, Manuel</au><au>Sundermeyer, Jörg</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Quinoline-8-olato-chromium catalysts with pseudohalogen effects for the CO2/cyclohexene epoxide copolymerization</atitle><jtitle>European polymer journal</jtitle><date>2019-11-01</date><risdate>2019</risdate><volume>120</volume><spage>109245</spage><pages>109245-</pages><artnum>109245</artnum><issn>0014-3057</issn><eissn>1873-1945</eissn><abstract>[Display omitted]
Based on our previous studies utilizing CrIII catalysts with trifluoroacetate as labile ligand and an ansa-bis-quinoline-olato ligand as a chemically more robust variant compared to known salen-type N2O2 ligands, we synthesized and investigated a series of structurally similar quinoline-8-olato chromium complexes with different active (pseudo-)halogen ligands X in [(babhq)CrX], (babhq = 2,2′-(butyl-azanediyl)bis(quinolin-8-olate), X = Cl, NCO, and N3. We demonstrate a high activity of these CrIII complexes in the solvent free carbon dioxide/cyclohexene oxide (CHO) copolymerization compared to the state of the art. In much deeper detail than in our previous communication, we altered the labile ligand X and undertook a catalyst screening on the polymerization parameters, such as pressure, temperature, and cocatalyst, i.e. [PPN]N3 (bis(triphenylphosphine)iminiun azide). The activity of the chromium systems was found to much depend on the labile (pseudo-)halogen ligand X and increases in the order Cl < NCO < N3. Especially the azide complex [(babhq)CrN3] displays a high activity, displaying a TOF of 2165 h−1 after 1 h of reaction time along with an induction period of 30 min. At longer reaction times, up to 94% monomer conversion selectively into the respective polycarbonate (pCHC) is observed.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.eurpolymj.2019.109245</doi></addata></record> |
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| subjects | Carbon dioxide Catalysts Chromium Chromium catalysts CO2/epoxide copolymerization Copolymerization Cyclohexene Ligands Organic chemistry Polycarbonates Polymerization Polymerization catalysis Quinoline Reaction time Ring-opening polymerization Studies |
| title | Quinoline-8-olato-chromium catalysts with pseudohalogen effects for the CO2/cyclohexene epoxide copolymerization |
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