Suzuki–Miyaura Catalyst-Transfer Polycondensation of Triolborate-Type Carbazole Monomers
Herein, we report the Suzuki–Miyaura catalyst-transfer polycondensation (SCTP) of triolborate-type carbazole monomers, i.e., potassium 3-(6-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl)triolborate (M1) and potassium 2-(7-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl) triolborate (M2), as an efficient and...
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Veröffentlicht in: | Polymers 2021-12, Vol.13 (23), p.4168 |
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description | Herein, we report the Suzuki–Miyaura catalyst-transfer polycondensation (SCTP) of triolborate-type carbazole monomers, i.e., potassium 3-(6-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl)triolborate (M1) and potassium 2-(7-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl) triolborate (M2), as an efficient and versatile approach for precisely synthesizing poly[9-(2-octyldodecyl)-3,6-carbazole] (3,6-PCz) and poly[9-(2-octyldodecyl)-2,7-carbazole] (2,7-PCz), respectively. The SCTP of triolborate-type carbazole monomers was performed in a mixture of THF/H2O using an initiating system consisted of 4-iodobenzyl alcohol, Pd2(dba)3•CHCl3, and t-Bu3P. In the SCTP of M1, cyclic by-product formation was confirmed, as reported for the corresponding pinacolboronate-type monomer. By optimizing the reaction temperature and reaction time, we successfully synthesized linear end-functionalized 3,6-PCz for the first time. The SCTP of M2 proceeded with almost no side reaction, yielding 2,7-PCz with a functional initiator residue at the α-chain end. Kinetic and block copolymerization experiments demonstrated that the SCTP of M2 proceeded in a chain-growth and controlled/living polymerization manner. This is a novel study on the synthesis of 2,7-PCz via SCTP. By taking advantage of the well-controlled nature of this polymerization system, we demonstrated the synthesis of high-molecular-weight 2,7-PCzs (Mn = 5–38 kg mol−1) with a relatively narrow ÐM (1.35–1.48). Furthermore, we successfully synthesized fluorene/carbazole copolymers as well as 2,7-PCz-containing diblock copolymers, demonstrating the versatility of the present polymerization system as a novel synthetic strategy for well-defined polycarbazole-based materials. |
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The SCTP of triolborate-type carbazole monomers was performed in a mixture of THF/H2O using an initiating system consisted of 4-iodobenzyl alcohol, Pd2(dba)3•CHCl3, and t-Bu3P. In the SCTP of M1, cyclic by-product formation was confirmed, as reported for the corresponding pinacolboronate-type monomer. By optimizing the reaction temperature and reaction time, we successfully synthesized linear end-functionalized 3,6-PCz for the first time. The SCTP of M2 proceeded with almost no side reaction, yielding 2,7-PCz with a functional initiator residue at the α-chain end. Kinetic and block copolymerization experiments demonstrated that the SCTP of M2 proceeded in a chain-growth and controlled/living polymerization manner. This is a novel study on the synthesis of 2,7-PCz via SCTP. By taking advantage of the well-controlled nature of this polymerization system, we demonstrated the synthesis of high-molecular-weight 2,7-PCzs (Mn = 5–38 kg mol−1) with a relatively narrow ÐM (1.35–1.48). Furthermore, we successfully synthesized fluorene/carbazole copolymers as well as 2,7-PCz-containing diblock copolymers, demonstrating the versatility of the present polymerization system as a novel synthetic strategy for well-defined polycarbazole-based materials.</description><identifier>ISSN: 2073-4360</identifier><identifier>EISSN: 2073-4360</identifier><identifier>DOI: 10.3390/polym13234168</identifier><identifier>PMID: 34883672</identifier><language>eng</language><publisher>Basel: MDPI AG</publisher><subject>Block copolymers ; Carbazoles ; Catalysts ; Chemical synthesis ; Chloroform ; Copolymerization ; Molecular weight ; Monomers ; Polymerization ; Polymers ; Potassium ; Reaction time ; Spectrum analysis</subject><ispartof>Polymers, 2021-12, Vol.13 (23), p.4168</ispartof><rights>2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 by the authors. 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c469t-6d4f38e09751a218416eade054694f990203672cdb7fdf2e7f1e9db1ae5e7aac3</citedby><cites>FETCH-LOGICAL-c469t-6d4f38e09751a218416eade054694f990203672cdb7fdf2e7f1e9db1ae5e7aac3</cites><orcidid>0000-0001-5449-9642 ; 0000-0001-8276-4546 ; 0000-0002-3238-813X ; 0000-0003-3746-2084</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8659485/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8659485/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793</link.rule.ids></links><search><creatorcontrib>Kobayashi, Saburo</creatorcontrib><creatorcontrib>Ashiya, Mayoh</creatorcontrib><creatorcontrib>Yamamoto, Takuya</creatorcontrib><creatorcontrib>Tajima, Kenji</creatorcontrib><creatorcontrib>Yamamoto, Yasunori</creatorcontrib><creatorcontrib>Isono, Takuya</creatorcontrib><creatorcontrib>Satoh, Toshifumi</creatorcontrib><title>Suzuki–Miyaura Catalyst-Transfer Polycondensation of Triolborate-Type Carbazole Monomers</title><title>Polymers</title><description>Herein, we report the Suzuki–Miyaura catalyst-transfer polycondensation (SCTP) of triolborate-type carbazole monomers, i.e., potassium 3-(6-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl)triolborate (M1) and potassium 2-(7-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl) triolborate (M2), as an efficient and versatile approach for precisely synthesizing poly[9-(2-octyldodecyl)-3,6-carbazole] (3,6-PCz) and poly[9-(2-octyldodecyl)-2,7-carbazole] (2,7-PCz), respectively. The SCTP of triolborate-type carbazole monomers was performed in a mixture of THF/H2O using an initiating system consisted of 4-iodobenzyl alcohol, Pd2(dba)3•CHCl3, and t-Bu3P. In the SCTP of M1, cyclic by-product formation was confirmed, as reported for the corresponding pinacolboronate-type monomer. By optimizing the reaction temperature and reaction time, we successfully synthesized linear end-functionalized 3,6-PCz for the first time. The SCTP of M2 proceeded with almost no side reaction, yielding 2,7-PCz with a functional initiator residue at the α-chain end. Kinetic and block copolymerization experiments demonstrated that the SCTP of M2 proceeded in a chain-growth and controlled/living polymerization manner. This is a novel study on the synthesis of 2,7-PCz via SCTP. By taking advantage of the well-controlled nature of this polymerization system, we demonstrated the synthesis of high-molecular-weight 2,7-PCzs (Mn = 5–38 kg mol−1) with a relatively narrow ÐM (1.35–1.48). Furthermore, we successfully synthesized fluorene/carbazole copolymers as well as 2,7-PCz-containing diblock copolymers, demonstrating the versatility of the present polymerization system as a novel synthetic strategy for well-defined polycarbazole-based materials.</description><subject>Block copolymers</subject><subject>Carbazoles</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chloroform</subject><subject>Copolymerization</subject><subject>Molecular weight</subject><subject>Monomers</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Potassium</subject><subject>Reaction time</subject><subject>Spectrum analysis</subject><issn>2073-4360</issn><issn>2073-4360</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNpVUU1Lw0AQXUSxpfboPeA5upvdbDYXQYpf0KJgvXhZJsmspqbZupsI6cn_4D_0l5jSInYuM_DevDfDI-SU0XPOU3qxslW3ZDzigkl1QIYRTXgouKSH_-YBGXu_oH2JWEqWHJMBF0pxmURD8vLUrtv38ufre1Z20DoIJtBA1fkmnDuovUEXPPYuua0LrD00pa0Da4K5K22VWQcNhvNuhf2ay2BtKwxmtrZLdP6EHBmoPI53fUSeb67nk7tw-nB7P7mahrmQaRPKQhiukKZJzCBiqn8FoUAa96gwaUojujk1L7LEFCbCxDBMi4wBxpgA5HxELre6qzZbYpFj3Tio9MqVS3CdtlDqfaQu3_Sr_dRKxqlQcS9wthNw9qNF3-iFbV3d36wjSRXjXCnRs8ItK3fWe4fmz4FRvUlD76XBfwFNiIAt</recordid><startdate>20211201</startdate><enddate>20211201</enddate><creator>Kobayashi, Saburo</creator><creator>Ashiya, Mayoh</creator><creator>Yamamoto, Takuya</creator><creator>Tajima, Kenji</creator><creator>Yamamoto, Yasunori</creator><creator>Isono, Takuya</creator><creator>Satoh, Toshifumi</creator><general>MDPI AG</general><general>MDPI</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-5449-9642</orcidid><orcidid>https://orcid.org/0000-0001-8276-4546</orcidid><orcidid>https://orcid.org/0000-0002-3238-813X</orcidid><orcidid>https://orcid.org/0000-0003-3746-2084</orcidid></search><sort><creationdate>20211201</creationdate><title>Suzuki–Miyaura Catalyst-Transfer Polycondensation of Triolborate-Type Carbazole Monomers</title><author>Kobayashi, Saburo ; Ashiya, Mayoh ; Yamamoto, Takuya ; Tajima, Kenji ; Yamamoto, Yasunori ; Isono, Takuya ; Satoh, Toshifumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c469t-6d4f38e09751a218416eade054694f990203672cdb7fdf2e7f1e9db1ae5e7aac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Block copolymers</topic><topic>Carbazoles</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Chloroform</topic><topic>Copolymerization</topic><topic>Molecular weight</topic><topic>Monomers</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Potassium</topic><topic>Reaction time</topic><topic>Spectrum analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kobayashi, Saburo</creatorcontrib><creatorcontrib>Ashiya, Mayoh</creatorcontrib><creatorcontrib>Yamamoto, Takuya</creatorcontrib><creatorcontrib>Tajima, Kenji</creatorcontrib><creatorcontrib>Yamamoto, Yasunori</creatorcontrib><creatorcontrib>Isono, Takuya</creatorcontrib><creatorcontrib>Satoh, Toshifumi</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kobayashi, Saburo</au><au>Ashiya, Mayoh</au><au>Yamamoto, Takuya</au><au>Tajima, Kenji</au><au>Yamamoto, Yasunori</au><au>Isono, Takuya</au><au>Satoh, Toshifumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Suzuki–Miyaura Catalyst-Transfer Polycondensation of Triolborate-Type Carbazole Monomers</atitle><jtitle>Polymers</jtitle><date>2021-12-01</date><risdate>2021</risdate><volume>13</volume><issue>23</issue><spage>4168</spage><pages>4168-</pages><issn>2073-4360</issn><eissn>2073-4360</eissn><abstract>Herein, we report the Suzuki–Miyaura catalyst-transfer polycondensation (SCTP) of triolborate-type carbazole monomers, i.e., potassium 3-(6-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl)triolborate (M1) and potassium 2-(7-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl) triolborate (M2), as an efficient and versatile approach for precisely synthesizing poly[9-(2-octyldodecyl)-3,6-carbazole] (3,6-PCz) and poly[9-(2-octyldodecyl)-2,7-carbazole] (2,7-PCz), respectively. The SCTP of triolborate-type carbazole monomers was performed in a mixture of THF/H2O using an initiating system consisted of 4-iodobenzyl alcohol, Pd2(dba)3•CHCl3, and t-Bu3P. In the SCTP of M1, cyclic by-product formation was confirmed, as reported for the corresponding pinacolboronate-type monomer. By optimizing the reaction temperature and reaction time, we successfully synthesized linear end-functionalized 3,6-PCz for the first time. The SCTP of M2 proceeded with almost no side reaction, yielding 2,7-PCz with a functional initiator residue at the α-chain end. Kinetic and block copolymerization experiments demonstrated that the SCTP of M2 proceeded in a chain-growth and controlled/living polymerization manner. This is a novel study on the synthesis of 2,7-PCz via SCTP. By taking advantage of the well-controlled nature of this polymerization system, we demonstrated the synthesis of high-molecular-weight 2,7-PCzs (Mn = 5–38 kg mol−1) with a relatively narrow ÐM (1.35–1.48). Furthermore, we successfully synthesized fluorene/carbazole copolymers as well as 2,7-PCz-containing diblock copolymers, demonstrating the versatility of the present polymerization system as a novel synthetic strategy for well-defined polycarbazole-based materials.</abstract><cop>Basel</cop><pub>MDPI AG</pub><pmid>34883672</pmid><doi>10.3390/polym13234168</doi><orcidid>https://orcid.org/0000-0001-5449-9642</orcidid><orcidid>https://orcid.org/0000-0001-8276-4546</orcidid><orcidid>https://orcid.org/0000-0002-3238-813X</orcidid><orcidid>https://orcid.org/0000-0003-3746-2084</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Block copolymers Carbazoles Catalysts Chemical synthesis Chloroform Copolymerization Molecular weight Monomers Polymerization Polymers Potassium Reaction time Spectrum analysis |
title | Suzuki–Miyaura Catalyst-Transfer Polycondensation of Triolborate-Type Carbazole Monomers |
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