A robust nickel catalyst with an unsymmetrical propyl-bridged diphosphine ligand for catalyst-transfer polymerization
A new nickel diphosphine catalyst has been synthesized in which the bidentate ligand has two different phosphine donors, a typical PPh 2 group and a stronger σ-donating PEt 2 group. The catalyst was highly effective for the chain-growth polymerization of a 3-alkylthiophene monomer using a Suzuki–Miy...
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| Veröffentlicht in: | Polymer journal 2020-01, Vol.52 (1), p.83-92 |
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| container_title | Polymer journal |
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| creator | Baker, Matthew A. Ayuso-Carrillo, Josué Koos, Martin R. M. MacMillan, Samantha N. Varni, Anthony J. Gil, Roberto R. Noonan, Kevin J. T. |
| description | A new nickel diphosphine catalyst has been synthesized in which the bidentate ligand has two different phosphine donors, a typical PPh
2
group and a stronger σ-donating PEt
2
group. The catalyst was highly effective for the chain-growth polymerization of a 3-alkylthiophene monomer using a Suzuki–Miyaura cross-coupling. The catalyst is particularly effective for this polymerization in the presence of excess free ligand. The unsymmetrical diphosphine nickel complex reported here represents a new approach to tuning metal-ligand reactivity in the chain-growth polymerization of aromatic monomers. In addition, this new nickel catalyst exhibited increased hydrolytic resistance in the polymerization as compared to commercially available 1,3-bis(diphenylphosphino)propane nickel dichloride.
A new nickel diphosphine catalyst was synthesized and evaluated for Suzuki–Miyaura cross-coupling polymerization. The diphosphine is comprised of two electronically and sterically distinct phosphine donors, a PPh
2
group and a PEt
2
group. The catalyst was employed to bring about controlled polymerization of a 3-hexylthiophene monomer to afford poly(3-hexylthiophene). The catalyst was particularly effective for bringing about this polymerization in the presence of excess free ligand. The catalyst resting state was also probed using NMR spectroscopy and an externally initiated catalyst. |
| doi_str_mv | 10.1038/s41428-019-0259-3 |
| format | Article |
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2
group and a stronger σ-donating PEt
2
group. The catalyst was highly effective for the chain-growth polymerization of a 3-alkylthiophene monomer using a Suzuki–Miyaura cross-coupling. The catalyst is particularly effective for this polymerization in the presence of excess free ligand. The unsymmetrical diphosphine nickel complex reported here represents a new approach to tuning metal-ligand reactivity in the chain-growth polymerization of aromatic monomers. In addition, this new nickel catalyst exhibited increased hydrolytic resistance in the polymerization as compared to commercially available 1,3-bis(diphenylphosphino)propane nickel dichloride.
A new nickel diphosphine catalyst was synthesized and evaluated for Suzuki–Miyaura cross-coupling polymerization. The diphosphine is comprised of two electronically and sterically distinct phosphine donors, a PPh
2
group and a PEt
2
group. The catalyst was employed to bring about controlled polymerization of a 3-hexylthiophene monomer to afford poly(3-hexylthiophene). The catalyst was particularly effective for bringing about this polymerization in the presence of excess free ligand. The catalyst resting state was also probed using NMR spectroscopy and an externally initiated catalyst.</description><identifier>ISSN: 0032-3896</identifier><identifier>EISSN: 1349-0540</identifier><identifier>DOI: 10.1038/s41428-019-0259-3</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>119/118 ; 140/131 ; 639/638/455/954 ; 639/638/77/884 ; Addition polymerization ; Biomaterials ; Bioorganic Chemistry ; Catalysts ; Chains (polymeric) ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Corrosion resistance ; Cross coupling ; Dichlorides ; Ligands ; Monomers ; Nickel ; Original Article ; Phosphines ; Polymer Sciences ; Polymerization ; Surfaces and Interfaces ; Thin Films</subject><ispartof>Polymer journal, 2020-01, Vol.52 (1), p.83-92</ispartof><rights>The Society of Polymer Science, Japan 2019</rights><rights>Copyright Nature Publishing Group Jan 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-2cb4317a84ad955dbfbfd83b1a4043584204bcca5e2f6f941b35a79514c17073</citedby><cites>FETCH-LOGICAL-c353t-2cb4317a84ad955dbfbfd83b1a4043584204bcca5e2f6f941b35a79514c17073</cites><orcidid>0000-0002-7829-4729 ; 0000-0003-4061-7593 ; 0000-0002-8810-5047 ; 0000-0001-6516-1823</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Baker, Matthew A.</creatorcontrib><creatorcontrib>Ayuso-Carrillo, Josué</creatorcontrib><creatorcontrib>Koos, Martin R. M.</creatorcontrib><creatorcontrib>MacMillan, Samantha N.</creatorcontrib><creatorcontrib>Varni, Anthony J.</creatorcontrib><creatorcontrib>Gil, Roberto R.</creatorcontrib><creatorcontrib>Noonan, Kevin J. T.</creatorcontrib><title>A robust nickel catalyst with an unsymmetrical propyl-bridged diphosphine ligand for catalyst-transfer polymerization</title><title>Polymer journal</title><addtitle>Polym J</addtitle><description>A new nickel diphosphine catalyst has been synthesized in which the bidentate ligand has two different phosphine donors, a typical PPh
2
group and a stronger σ-donating PEt
2
group. The catalyst was highly effective for the chain-growth polymerization of a 3-alkylthiophene monomer using a Suzuki–Miyaura cross-coupling. The catalyst is particularly effective for this polymerization in the presence of excess free ligand. The unsymmetrical diphosphine nickel complex reported here represents a new approach to tuning metal-ligand reactivity in the chain-growth polymerization of aromatic monomers. In addition, this new nickel catalyst exhibited increased hydrolytic resistance in the polymerization as compared to commercially available 1,3-bis(diphenylphosphino)propane nickel dichloride.
A new nickel diphosphine catalyst was synthesized and evaluated for Suzuki–Miyaura cross-coupling polymerization. The diphosphine is comprised of two electronically and sterically distinct phosphine donors, a PPh
2
group and a PEt
2
group. The catalyst was employed to bring about controlled polymerization of a 3-hexylthiophene monomer to afford poly(3-hexylthiophene). The catalyst was particularly effective for bringing about this polymerization in the presence of excess free ligand. The catalyst resting state was also probed using NMR spectroscopy and an externally initiated catalyst.</description><subject>119/118</subject><subject>140/131</subject><subject>639/638/455/954</subject><subject>639/638/77/884</subject><subject>Addition polymerization</subject><subject>Biomaterials</subject><subject>Bioorganic Chemistry</subject><subject>Catalysts</subject><subject>Chains (polymeric)</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Corrosion resistance</subject><subject>Cross coupling</subject><subject>Dichlorides</subject><subject>Ligands</subject><subject>Monomers</subject><subject>Nickel</subject><subject>Original Article</subject><subject>Phosphines</subject><subject>Polymer Sciences</subject><subject>Polymerization</subject><subject>Surfaces and Interfaces</subject><subject>Thin Films</subject><issn>0032-3896</issn><issn>1349-0540</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNp1kE1LwzAYx4MoOKcfwFvAczSva3scwzcYeNk9JGm6ZbZpTVKkfnozKnry9PCH_8vDD4Bbgu8JZuVD5ITTEmFSIUxFhdgZWBDGsxIcn4MFxowiVlarS3AV4xFjuhKYL8C4hqHXY0zQO_NuW2hUUu2U9adLB6g8HH2cus6m4Ixq4RD6YWqRDq7e2xrWbjj0cTg4b2Hr9srXsOnDbwlKQfnY2ACHvp06G9yXSq731-CiUW20Nz93CXZPj7vNC9q-Pb9u1ltkmGAJUaM5I4UquaorIWrd6KYumSaKY85EySnm2hglLG1WTcWJZkIVlSDckAIXbAnu5tr89cdoY5LHfgw-L0rKKCWMclZlF5ldJvQxBtvIIbhOhUkSLE9w5QxXZrjyBFeynKFzJmav39vw1_x_6BuNcn9Q</recordid><startdate>20200101</startdate><enddate>20200101</enddate><creator>Baker, Matthew A.</creator><creator>Ayuso-Carrillo, Josué</creator><creator>Koos, Martin R. 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M. ; MacMillan, Samantha N. ; Varni, Anthony J. ; Gil, Roberto R. ; Noonan, Kevin J. T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-2cb4317a84ad955dbfbfd83b1a4043584204bcca5e2f6f941b35a79514c17073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>119/118</topic><topic>140/131</topic><topic>639/638/455/954</topic><topic>639/638/77/884</topic><topic>Addition polymerization</topic><topic>Biomaterials</topic><topic>Bioorganic Chemistry</topic><topic>Catalysts</topic><topic>Chains (polymeric)</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Corrosion resistance</topic><topic>Cross coupling</topic><topic>Dichlorides</topic><topic>Ligands</topic><topic>Monomers</topic><topic>Nickel</topic><topic>Original Article</topic><topic>Phosphines</topic><topic>Polymer Sciences</topic><topic>Polymerization</topic><topic>Surfaces and Interfaces</topic><topic>Thin Films</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Baker, Matthew A.</creatorcontrib><creatorcontrib>Ayuso-Carrillo, Josué</creatorcontrib><creatorcontrib>Koos, Martin R. M.</creatorcontrib><creatorcontrib>MacMillan, Samantha N.</creatorcontrib><creatorcontrib>Varni, Anthony J.</creatorcontrib><creatorcontrib>Gil, Roberto R.</creatorcontrib><creatorcontrib>Noonan, Kevin J. 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M.</au><au>MacMillan, Samantha N.</au><au>Varni, Anthony J.</au><au>Gil, Roberto R.</au><au>Noonan, Kevin J. T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A robust nickel catalyst with an unsymmetrical propyl-bridged diphosphine ligand for catalyst-transfer polymerization</atitle><jtitle>Polymer journal</jtitle><stitle>Polym J</stitle><date>2020-01-01</date><risdate>2020</risdate><volume>52</volume><issue>1</issue><spage>83</spage><epage>92</epage><pages>83-92</pages><issn>0032-3896</issn><eissn>1349-0540</eissn><abstract>A new nickel diphosphine catalyst has been synthesized in which the bidentate ligand has two different phosphine donors, a typical PPh
2
group and a stronger σ-donating PEt
2
group. The catalyst was highly effective for the chain-growth polymerization of a 3-alkylthiophene monomer using a Suzuki–Miyaura cross-coupling. The catalyst is particularly effective for this polymerization in the presence of excess free ligand. The unsymmetrical diphosphine nickel complex reported here represents a new approach to tuning metal-ligand reactivity in the chain-growth polymerization of aromatic monomers. In addition, this new nickel catalyst exhibited increased hydrolytic resistance in the polymerization as compared to commercially available 1,3-bis(diphenylphosphino)propane nickel dichloride.
A new nickel diphosphine catalyst was synthesized and evaluated for Suzuki–Miyaura cross-coupling polymerization. The diphosphine is comprised of two electronically and sterically distinct phosphine donors, a PPh
2
group and a PEt
2
group. The catalyst was employed to bring about controlled polymerization of a 3-hexylthiophene monomer to afford poly(3-hexylthiophene). The catalyst was particularly effective for bringing about this polymerization in the presence of excess free ligand. The catalyst resting state was also probed using NMR spectroscopy and an externally initiated catalyst.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><doi>10.1038/s41428-019-0259-3</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-7829-4729</orcidid><orcidid>https://orcid.org/0000-0003-4061-7593</orcidid><orcidid>https://orcid.org/0000-0002-8810-5047</orcidid><orcidid>https://orcid.org/0000-0001-6516-1823</orcidid></addata></record> |
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| source | Alma/SFX Local Collection |
| subjects | 119/118 140/131 639/638/455/954 639/638/77/884 Addition polymerization Biomaterials Bioorganic Chemistry Catalysts Chains (polymeric) Chemical synthesis Chemistry Chemistry and Materials Science Chemistry/Food Science Corrosion resistance Cross coupling Dichlorides Ligands Monomers Nickel Original Article Phosphines Polymer Sciences Polymerization Surfaces and Interfaces Thin Films |
| title | A robust nickel catalyst with an unsymmetrical propyl-bridged diphosphine ligand for catalyst-transfer polymerization |
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