Mechanochemical Release of N‐Heterocyclic Carbenes from Flex‐Activated Mechanophores
We have discovered a new flex‐activated mechanophore that releases an N‐heterocyclic carbene (NHC) under mechanical load. The mechanophore design is based upon NHC‐carbodiimide (NHC‐CDI) adducts and demonstrates an important first step toward flex‐activated designs capable of further downstream reac...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2021-06, Vol.60 (24), p.13559-13563 |
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| creator | Shen, Hang Larsen, Michael B. Roessler, Allison G. Zimmerman, Paul M. Boydston, Andrew J. |
| description | We have discovered a new flex‐activated mechanophore that releases an N‐heterocyclic carbene (NHC) under mechanical load. The mechanophore design is based upon NHC‐carbodiimide (NHC‐CDI) adducts and demonstrates an important first step toward flex‐activated designs capable of further downstream reactivities. Since the flex‐activation is non‐destructive to the main polymer chains, the material can be subjected to multiple compression cycles to achieve iterative increases in the activation percentage of mechanophores. Two different NHC structures were demonstrated, signifying the potential modularity of the mechanophore design.
A new kind of flex‐activated mechanophore, N‐heterocyclic carbene–carbodiimide adduct (NHC‐CDI), was developed as a platform to release different NHCs under mechanical load. The polymeric materials containing NHC‐CDI can be subjected to multiple compression cycles and successively release NHCs, which have potential to be utilized as self‐healing, self‐strengthening and self‐reporting materials. |
| doi_str_mv | 10.1002/anie.202100576 |
| format | Article |
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A new kind of flex‐activated mechanophore, N‐heterocyclic carbene–carbodiimide adduct (NHC‐CDI), was developed as a platform to release different NHCs under mechanical load. The polymeric materials containing NHC‐CDI can be subjected to multiple compression cycles and successively release NHCs, which have potential to be utilized as self‐healing, self‐strengthening and self‐reporting materials.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202100576</identifier><identifier>PMID: 33826803</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Carbenes ; Carbodiimide ; Compression ; Mechanical properties ; mechanochemistry ; mechanophores ; mechanoresponsive polymers ; Modularity ; N-heterocyclic carbene ; N-heterocyclic carbene–carbodiimide ; Polymers</subject><ispartof>Angewandte Chemie International Edition, 2021-06, Vol.60 (24), p.13559-13563</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2021 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5166-5d2e320420ffdc579bbc67e56a6e3963b8d511293f58af71ef0373afd33e14fb3</citedby><cites>FETCH-LOGICAL-c5166-5d2e320420ffdc579bbc67e56a6e3963b8d511293f58af71ef0373afd33e14fb3</cites><orcidid>0000-0002-2511-0922 ; 0000-0002-0324-4938 ; 0000-0001-7192-4903</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.202100576$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202100576$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33826803$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shen, Hang</creatorcontrib><creatorcontrib>Larsen, Michael B.</creatorcontrib><creatorcontrib>Roessler, Allison G.</creatorcontrib><creatorcontrib>Zimmerman, Paul M.</creatorcontrib><creatorcontrib>Boydston, Andrew J.</creatorcontrib><title>Mechanochemical Release of N‐Heterocyclic Carbenes from Flex‐Activated Mechanophores</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>We have discovered a new flex‐activated mechanophore that releases an N‐heterocyclic carbene (NHC) under mechanical load. The mechanophore design is based upon NHC‐carbodiimide (NHC‐CDI) adducts and demonstrates an important first step toward flex‐activated designs capable of further downstream reactivities. Since the flex‐activation is non‐destructive to the main polymer chains, the material can be subjected to multiple compression cycles to achieve iterative increases in the activation percentage of mechanophores. Two different NHC structures were demonstrated, signifying the potential modularity of the mechanophore design.
A new kind of flex‐activated mechanophore, N‐heterocyclic carbene–carbodiimide adduct (NHC‐CDI), was developed as a platform to release different NHCs under mechanical load. The polymeric materials containing NHC‐CDI can be subjected to multiple compression cycles and successively release NHCs, which have potential to be utilized as self‐healing, self‐strengthening and self‐reporting materials.</description><subject>Adducts</subject><subject>Carbenes</subject><subject>Carbodiimide</subject><subject>Compression</subject><subject>Mechanical properties</subject><subject>mechanochemistry</subject><subject>mechanophores</subject><subject>mechanoresponsive polymers</subject><subject>Modularity</subject><subject>N-heterocyclic carbene</subject><subject>N-heterocyclic carbene–carbodiimide</subject><subject>Polymers</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqF0MtKxDAUBuAgivetSym4cdMxyWmSdjkM4wW8gCi4K2l6wlTaZkxm1Nn5CD6jT2JkRgU3rnIC3_k5_IQcMDpglPIT3Tc44JTHj1ByjWwzwVkKSsF6nDOAVOWCbZGdEB6jz3MqN8kWQM5lTmGbPFyhmejemQl2jdFtcost6oCJs8n1x9v7Oc7QO7MwbWOSkfYV9hgS612XnLb4GsXQzJpnPcM6WUVNJ85j2CMbVrcB91fvLrk_Hd-NztPLm7OL0fAyNYJJmYqaI3CacWptbYQqqspIhUJqiVBIqPJaMMYLsCLXVjG0FBRoWwMgy2wFu-R4mTv17mmOYVZ2TTDYtrpHNw8lF4xyKRnnkR79oY9u7vt4XVQgMpkpWUQ1WCrjXQgebTn1Taf9omS0_Oq8_Oq8_Ok8LhyuYudVh_UP_y45gmIJXpoWF__ElcPri_Fv-Cdy3o8E</recordid><startdate>20210607</startdate><enddate>20210607</enddate><creator>Shen, Hang</creator><creator>Larsen, Michael B.</creator><creator>Roessler, Allison G.</creator><creator>Zimmerman, Paul M.</creator><creator>Boydston, Andrew J.</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/0000-0002-2511-0922</orcidid><orcidid>https://orcid.org/0000-0002-0324-4938</orcidid><orcidid>https://orcid.org/0000-0001-7192-4903</orcidid></search><sort><creationdate>20210607</creationdate><title>Mechanochemical Release of N‐Heterocyclic Carbenes from Flex‐Activated Mechanophores</title><author>Shen, Hang ; Larsen, Michael B. ; Roessler, Allison G. ; Zimmerman, Paul M. ; Boydston, Andrew J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5166-5d2e320420ffdc579bbc67e56a6e3963b8d511293f58af71ef0373afd33e14fb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Adducts</topic><topic>Carbenes</topic><topic>Carbodiimide</topic><topic>Compression</topic><topic>Mechanical properties</topic><topic>mechanochemistry</topic><topic>mechanophores</topic><topic>mechanoresponsive polymers</topic><topic>Modularity</topic><topic>N-heterocyclic carbene</topic><topic>N-heterocyclic carbene–carbodiimide</topic><topic>Polymers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shen, Hang</creatorcontrib><creatorcontrib>Larsen, Michael B.</creatorcontrib><creatorcontrib>Roessler, Allison G.</creatorcontrib><creatorcontrib>Zimmerman, Paul M.</creatorcontrib><creatorcontrib>Boydston, Andrew J.</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>Shen, Hang</au><au>Larsen, Michael B.</au><au>Roessler, Allison G.</au><au>Zimmerman, Paul M.</au><au>Boydston, Andrew J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mechanochemical Release of N‐Heterocyclic Carbenes from Flex‐Activated Mechanophores</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2021-06-07</date><risdate>2021</risdate><volume>60</volume><issue>24</issue><spage>13559</spage><epage>13563</epage><pages>13559-13563</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>We have discovered a new flex‐activated mechanophore that releases an N‐heterocyclic carbene (NHC) under mechanical load. The mechanophore design is based upon NHC‐carbodiimide (NHC‐CDI) adducts and demonstrates an important first step toward flex‐activated designs capable of further downstream reactivities. Since the flex‐activation is non‐destructive to the main polymer chains, the material can be subjected to multiple compression cycles to achieve iterative increases in the activation percentage of mechanophores. Two different NHC structures were demonstrated, signifying the potential modularity of the mechanophore design.
A new kind of flex‐activated mechanophore, N‐heterocyclic carbene–carbodiimide adduct (NHC‐CDI), was developed as a platform to release different NHCs under mechanical load. The polymeric materials containing NHC‐CDI can be subjected to multiple compression cycles and successively release NHCs, which have potential to be utilized as self‐healing, self‐strengthening and self‐reporting materials.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>33826803</pmid><doi>10.1002/anie.202100576</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-2511-0922</orcidid><orcidid>https://orcid.org/0000-0002-0324-4938</orcidid><orcidid>https://orcid.org/0000-0001-7192-4903</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Adducts Carbenes Carbodiimide Compression Mechanical properties mechanochemistry mechanophores mechanoresponsive polymers Modularity N-heterocyclic carbene N-heterocyclic carbene–carbodiimide Polymers |
| title | Mechanochemical Release of N‐Heterocyclic Carbenes from Flex‐Activated Mechanophores |
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