A Diarylacetonitrile as a Molecular Probe for the Detection of Polymeric Mechanoradicals in the Bulk State through a Radical Chain‐Transfer Mechanism
Since the beginning of polymer science, understanding the influence of mechanical stress on polymer chains has been a fundamental and important research topic. The detection of mechanoradicals generated by homolytic cleavage of the polymer chains in solution has been studied in many cases. However,...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2021-02, Vol.60 (5), p.2680-2683 |
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| creator | Yamamoto, Takumi Kato, Sota Aoki, Daisuke Otsuka, Hideyuki |
| description | Since the beginning of polymer science, understanding the influence of mechanical stress on polymer chains has been a fundamental and important research topic. The detection of mechanoradicals generated by homolytic cleavage of the polymer chains in solution has been studied in many cases. However, the detection of mechanoradicals in the bulk is still limited owing to their high reactivity. Herein, we propose an innovative strategy to detect mechanoradicals visually and quantitatively using a chain‐transfer agent that generates relatively stable fluorescent radicals as a molecular probe. Mechanoradicals generated by ball milling of polystyrene samples were successfully detected by using a diarylacetonitrile compound as a fluorescent molecular probe through this radical chain‐transfer mechanism. This probe enables the visualization and quantitative evaluation of mechanoradicals generated by polymer‐chain scission.
A fluorescent molecular probe that functions as a scavenger of polymeric mechanoradicals was developed (see picture), and its fluorescence intensity was found to increase with increasing generation of radicals in the bulk. This probe enables the optical visualization and quantitative evaluation of polymeric radicals generated by polymer‐chain scission of polymers that do not contain mechanophores. |
| doi_str_mv | 10.1002/anie.202013180 |
| format | Article |
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A fluorescent molecular probe that functions as a scavenger of polymeric mechanoradicals was developed (see picture), and its fluorescence intensity was found to increase with increasing generation of radicals in the bulk. This probe enables the optical visualization and quantitative evaluation of polymeric radicals generated by polymer‐chain scission of polymers that do not contain mechanophores.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202013180</identifier><identifier>PMID: 33085132</identifier><language>eng</language><publisher>WEINHEIM: Wiley</publisher><subject>Ball milling ; Chain scission ; Chains (polymeric) ; Chemistry ; Chemistry, Multidisciplinary ; Fluorescence ; mechanochemistry ; molecular probes ; Physical Sciences ; Polymers ; Polystyrene ; Polystyrene resins ; Radicals ; Science & Technology</subject><ispartof>Angewandte Chemie International Edition, 2021-02, Vol.60 (5), p.2680-2683</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2020 Wiley-VCH GmbH.</rights><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>36</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000594471500001</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c4760-5d6f6ba41ba9337402346af53fa660a1bb90a92de61e0aa343538191655dacf63</citedby><cites>FETCH-LOGICAL-c4760-5d6f6ba41ba9337402346af53fa660a1bb90a92de61e0aa343538191655dacf63</cites><orcidid>0000-0002-1512-671X ; 0000-0002-7272-0643</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.202013180$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202013180$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27928,27929,39262,45578,45579</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33085132$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yamamoto, Takumi</creatorcontrib><creatorcontrib>Kato, Sota</creatorcontrib><creatorcontrib>Aoki, Daisuke</creatorcontrib><creatorcontrib>Otsuka, Hideyuki</creatorcontrib><title>A Diarylacetonitrile as a Molecular Probe for the Detection of Polymeric Mechanoradicals in the Bulk State through a Radical Chain‐Transfer Mechanism</title><title>Angewandte Chemie International Edition</title><addtitle>ANGEW CHEM INT EDIT</addtitle><addtitle>Angew Chem Int Ed Engl</addtitle><description>Since the beginning of polymer science, understanding the influence of mechanical stress on polymer chains has been a fundamental and important research topic. The detection of mechanoradicals generated by homolytic cleavage of the polymer chains in solution has been studied in many cases. However, the detection of mechanoradicals in the bulk is still limited owing to their high reactivity. Herein, we propose an innovative strategy to detect mechanoradicals visually and quantitatively using a chain‐transfer agent that generates relatively stable fluorescent radicals as a molecular probe. Mechanoradicals generated by ball milling of polystyrene samples were successfully detected by using a diarylacetonitrile compound as a fluorescent molecular probe through this radical chain‐transfer mechanism. This probe enables the visualization and quantitative evaluation of mechanoradicals generated by polymer‐chain scission.
A fluorescent molecular probe that functions as a scavenger of polymeric mechanoradicals was developed (see picture), and its fluorescence intensity was found to increase with increasing generation of radicals in the bulk. This probe enables the optical visualization and quantitative evaluation of polymeric radicals generated by polymer‐chain scission of polymers that do not contain mechanophores.</description><subject>Ball milling</subject><subject>Chain scission</subject><subject>Chains (polymeric)</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>Fluorescence</subject><subject>mechanochemistry</subject><subject>molecular probes</subject><subject>Physical Sciences</subject><subject>Polymers</subject><subject>Polystyrene</subject><subject>Polystyrene resins</subject><subject>Radicals</subject><subject>Science & Technology</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><recordid>eNqNksFu1DAQhi0EomXhyhFZ4oKEsthx7CTHbVqgUgsVlHM0ccasS2IXOxHaG4_AjffjSfCyyyJxgZPH1jefxv5NyGPOlpyx_AU4i8uc5YwLXrE75JjLnGeiLMXdVBdCZGUl-RF5EONN4quKqfvkSAiWTkV-TL6v6KmFsBlA4-SdnYIdkEKkQC_9gHoeINCr4Dukxgc6rZGe4oR6st5Rb-iVHzYjBqvpJeo1OB-gtxqGSK37RZ_Mwyf6foIJ0zb4-eM6qd_tINqswbofX79dB3DRYNhLbBwfknsmWfDRfl2QDy_PrpvX2cXbV-fN6iLTRalYJntlVAcF76AWoixYLgoFRgoDSjHgXVczqPMeFUcGIAohRcVrrqTsQRslFuTZznsb_OcZ49SONmocBnDo59jmhczrUql6iz79C73xc3BpukRVLDm5FIla7igdfIwBTXsb7JheuOWs3UbWbiNrD5Glhid77dyN2B_w3xkl4PkO-IKdN1FbdBoPGGNM1kVRcpmqpFyQ6v_pxqZgUpKNn92UWut9a_oDm3_M3a7enJ_9ucVPC3PElA</recordid><startdate>20210201</startdate><enddate>20210201</enddate><creator>Yamamoto, Takumi</creator><creator>Kato, Sota</creator><creator>Aoki, Daisuke</creator><creator>Otsuka, Hideyuki</creator><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1512-671X</orcidid><orcidid>https://orcid.org/0000-0002-7272-0643</orcidid></search><sort><creationdate>20210201</creationdate><title>A Diarylacetonitrile as a Molecular Probe for the Detection of Polymeric Mechanoradicals in the Bulk State through a Radical Chain‐Transfer Mechanism</title><author>Yamamoto, Takumi ; Kato, Sota ; Aoki, Daisuke ; Otsuka, Hideyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4760-5d6f6ba41ba9337402346af53fa660a1bb90a92de61e0aa343538191655dacf63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Ball milling</topic><topic>Chain scission</topic><topic>Chains (polymeric)</topic><topic>Chemistry</topic><topic>Chemistry, Multidisciplinary</topic><topic>Fluorescence</topic><topic>mechanochemistry</topic><topic>molecular probes</topic><topic>Physical Sciences</topic><topic>Polymers</topic><topic>Polystyrene</topic><topic>Polystyrene resins</topic><topic>Radicals</topic><topic>Science & Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamamoto, Takumi</creatorcontrib><creatorcontrib>Kato, Sota</creatorcontrib><creatorcontrib>Aoki, Daisuke</creatorcontrib><creatorcontrib>Otsuka, Hideyuki</creatorcontrib><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><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>Yamamoto, Takumi</au><au>Kato, Sota</au><au>Aoki, Daisuke</au><au>Otsuka, Hideyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Diarylacetonitrile as a Molecular Probe for the Detection of Polymeric Mechanoradicals in the Bulk State through a Radical Chain‐Transfer Mechanism</atitle><jtitle>Angewandte Chemie International Edition</jtitle><stitle>ANGEW CHEM INT EDIT</stitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2021-02-01</date><risdate>2021</risdate><volume>60</volume><issue>5</issue><spage>2680</spage><epage>2683</epage><pages>2680-2683</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Since the beginning of polymer science, understanding the influence of mechanical stress on polymer chains has been a fundamental and important research topic. The detection of mechanoradicals generated by homolytic cleavage of the polymer chains in solution has been studied in many cases. However, the detection of mechanoradicals in the bulk is still limited owing to their high reactivity. Herein, we propose an innovative strategy to detect mechanoradicals visually and quantitatively using a chain‐transfer agent that generates relatively stable fluorescent radicals as a molecular probe. Mechanoradicals generated by ball milling of polystyrene samples were successfully detected by using a diarylacetonitrile compound as a fluorescent molecular probe through this radical chain‐transfer mechanism. This probe enables the visualization and quantitative evaluation of mechanoradicals generated by polymer‐chain scission.
A fluorescent molecular probe that functions as a scavenger of polymeric mechanoradicals was developed (see picture), and its fluorescence intensity was found to increase with increasing generation of radicals in the bulk. This probe enables the optical visualization and quantitative evaluation of polymeric radicals generated by polymer‐chain scission of polymers that do not contain mechanophores.</abstract><cop>WEINHEIM</cop><pub>Wiley</pub><pmid>33085132</pmid><doi>10.1002/anie.202013180</doi><tpages>4</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-1512-671X</orcidid><orcidid>https://orcid.org/0000-0002-7272-0643</orcidid></addata></record> |
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| subjects | Ball milling Chain scission Chains (polymeric) Chemistry Chemistry, Multidisciplinary Fluorescence mechanochemistry molecular probes Physical Sciences Polymers Polystyrene Polystyrene resins Radicals Science & Technology |
| title | A Diarylacetonitrile as a Molecular Probe for the Detection of Polymeric Mechanoradicals in the Bulk State through a Radical Chain‐Transfer Mechanism |
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