Rhodium‐Catalyzed Stitching Polymerization of 1,5‐Hexadiynes and Related Oligoalkynes
A new mode of polymerization, rhodium‐catalyzed stitching polymerization, has been developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated 1,5‐hexadiynes containing both terminal and internal alkyne moieties as monomers. The polymerization proceeded smoot...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2019-04, Vol.58 (17), p.5734-5738 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Ikeda, Sho Shintani, Ryo |
| description | A new mode of polymerization, rhodium‐catalyzed stitching polymerization, has been developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated 1,5‐hexadiynes containing both terminal and internal alkyne moieties as monomers. The polymerization proceeded smoothly with a high degree of stitching efficiency under mild conditions, and 1,5,9‐decatriyne and 1,5,9,13‐tetradecatetrayne monomers could also be employed. The present polymerization strategy would be particularly beneficial for the synthesis of polymers consisting of a repeating unit that is difficult to prepare as a stable monomer because it does not require the use of a preformed bridged π‐conjugated monomer.
A stitch in time saves… the preparation of a bridged π‐conjugated monomer: The title polymerization mode was developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated oligoalkyne monomers containing both terminal and internal alkyne moieties (see scheme). The polymerization proceeded smoothly with a high degree of stitching efficiency under mild conditions. |
| doi_str_mv | 10.1002/anie.201901148 |
| format | Article |
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A stitch in time saves… the preparation of a bridged π‐conjugated monomer: The title polymerization mode was developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated oligoalkyne monomers containing both terminal and internal alkyne moieties (see scheme). The polymerization proceeded smoothly with a high degree of stitching efficiency under mild conditions.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201901148</identifier><identifier>PMID: 30838747</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Chemical synthesis ; diynes ; Monomers ; oligoalkynes ; Polymerization ; Polymers ; Rhodium ; rhodium catalysis ; Stitching ; π-conjugated polymers</subject><ispartof>Angewandte Chemie International Edition, 2019-04, Vol.58 (17), p.5734-5738</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4768-3383d772490239ae74fba5824ac8f70913449a778d407028eefb7ced15af94243</citedby><cites>FETCH-LOGICAL-c4768-3383d772490239ae74fba5824ac8f70913449a778d407028eefb7ced15af94243</cites><orcidid>0000-0002-3324-9393</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201901148$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201901148$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30838747$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ikeda, Sho</creatorcontrib><creatorcontrib>Shintani, Ryo</creatorcontrib><title>Rhodium‐Catalyzed Stitching Polymerization of 1,5‐Hexadiynes and Related Oligoalkynes</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A new mode of polymerization, rhodium‐catalyzed stitching polymerization, has been developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated 1,5‐hexadiynes containing both terminal and internal alkyne moieties as monomers. The polymerization proceeded smoothly with a high degree of stitching efficiency under mild conditions, and 1,5,9‐decatriyne and 1,5,9,13‐tetradecatetrayne monomers could also be employed. The present polymerization strategy would be particularly beneficial for the synthesis of polymers consisting of a repeating unit that is difficult to prepare as a stable monomer because it does not require the use of a preformed bridged π‐conjugated monomer.
A stitch in time saves… the preparation of a bridged π‐conjugated monomer: The title polymerization mode was developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated oligoalkyne monomers containing both terminal and internal alkyne moieties (see scheme). The polymerization proceeded smoothly with a high degree of stitching efficiency under mild conditions.</description><subject>Alkynes</subject><subject>Chemical synthesis</subject><subject>diynes</subject><subject>Monomers</subject><subject>oligoalkynes</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Rhodium</subject><subject>rhodium catalysis</subject><subject>Stitching</subject><subject>π-conjugated polymers</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqF0MtKxDAUBuAgipfRrUspuHFhx1wn6VIGbzCoeFm4Cpn2VKNpo02L1pWP4DP6JGYYL-DGVQL5zk_Oj9AmwUOCMd0ztYUhxSTDhHC1gFaJoCRlUrLFeOeMpVIJsoLWQriPXik8WkYrDCumJJer6Obizhe2qz7e3semNa5_hSK5bG2b39n6Njn3rq-gsa-mtb5OfJmQXRHtMbyYwvY1hMTURXIBzrRx8MzZW2_cw-xhHS2VxgXY-DoH6Prw4Gp8nE7Ojk7G-5M053KkUsYUK6SkPMOUZQYkL6dGKMpNrkqJM8I4z4yUquBYxgUAyqnMoSDClBmnnA3Qzjz3sfFPHYRWVzbk4JypwXdBU6KUUCPBR5Fu_6H3vmvq-DtNKRaUcyGzqIZzlTc-hAZK_djYyjS9JljPStez0vVP6XFg6yu2m1ZQ_PDvliPI5uDZOuj_idP7pycHv-Gfp6-Oxg</recordid><startdate>20190416</startdate><enddate>20190416</enddate><creator>Ikeda, Sho</creator><creator>Shintani, Ryo</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3324-9393</orcidid></search><sort><creationdate>20190416</creationdate><title>Rhodium‐Catalyzed Stitching Polymerization of 1,5‐Hexadiynes and Related Oligoalkynes</title><author>Ikeda, Sho ; Shintani, Ryo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4768-3383d772490239ae74fba5824ac8f70913449a778d407028eefb7ced15af94243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkynes</topic><topic>Chemical synthesis</topic><topic>diynes</topic><topic>Monomers</topic><topic>oligoalkynes</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Rhodium</topic><topic>rhodium catalysis</topic><topic>Stitching</topic><topic>π-conjugated polymers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ikeda, Sho</creatorcontrib><creatorcontrib>Shintani, Ryo</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ikeda, Sho</au><au>Shintani, Ryo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium‐Catalyzed Stitching Polymerization of 1,5‐Hexadiynes and Related Oligoalkynes</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-04-16</date><risdate>2019</risdate><volume>58</volume><issue>17</issue><spage>5734</spage><epage>5738</epage><pages>5734-5738</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A new mode of polymerization, rhodium‐catalyzed stitching polymerization, has been developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated 1,5‐hexadiynes containing both terminal and internal alkyne moieties as monomers. The polymerization proceeded smoothly with a high degree of stitching efficiency under mild conditions, and 1,5,9‐decatriyne and 1,5,9,13‐tetradecatetrayne monomers could also be employed. The present polymerization strategy would be particularly beneficial for the synthesis of polymers consisting of a repeating unit that is difficult to prepare as a stable monomer because it does not require the use of a preformed bridged π‐conjugated monomer.
A stitch in time saves… the preparation of a bridged π‐conjugated monomer: The title polymerization mode was developed for the synthesis of π‐conjugated polymers with bridged repeating units from nonconjugated oligoalkyne monomers containing both terminal and internal alkyne moieties (see scheme). The polymerization proceeded smoothly with a high degree of stitching efficiency under mild conditions.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30838747</pmid><doi>10.1002/anie.201901148</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-3324-9393</orcidid></addata></record> |
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| identifier | ISSN: 1433-7851 |
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| issn | 1433-7851 1521-3773 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkynes Chemical synthesis diynes Monomers oligoalkynes Polymerization Polymers Rhodium rhodium catalysis Stitching π-conjugated polymers |
| title | Rhodium‐Catalyzed Stitching Polymerization of 1,5‐Hexadiynes and Related Oligoalkynes |
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