1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones: Toward a New Class of Visible Type I Photoinitiators for Free Radical Polymerization of Methacrylates
1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones (SEDs) are proposed here as a new class of visible Type I photoinitiators (PIs) for free radical polymerization under air upon exposure to blue (@455 nm) and green (@520 nm) LEDs. Remarkably, these new systems present good polymerization performances and...
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| Veröffentlicht in: | Macromolecular rapid communications. 2019-10, Vol.40 (20), p.e1900319-n/a |
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| creator | Kirschner, Julie Baralle, Alexandre Graff, Bernadette Becht, Jean‐Michel Klee, Joachim E. Lalevée, Jacques |
| description | 1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones (SEDs) are proposed here as a new class of visible Type I photoinitiators (PIs) for free radical polymerization under air upon exposure to blue (@455 nm) and green (@520 nm) LEDs. Remarkably, these new systems present good polymerization performances and excellent bleaching properties compared to camphorquinone‐based systems, and transparent polymers are obtained upon visible light irradiation. Real‐time Fourier transform infrared spectroscopy is used to monitor the polymerization profiles. Molecular orbital calculations are also carried out for a better understanding of the structure/reactivity relationship of the photoinitiators.
1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones are presented here as a new class of visible Type I photoinitiators for free radical polymerization. These new systems present good polymerization performances and excellent bleaching properties compared to camphorquinone‐based systems, and transparent polymers are obtained upon visible‐light irradiation. The chemical mechanisms are also presented for a better understanding of their reactivity. |
| doi_str_mv | 10.1002/marc.201900319 |
| format | Article |
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1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones are presented here as a new class of visible Type I photoinitiators for free radical polymerization. These new systems present good polymerization performances and excellent bleaching properties compared to camphorquinone‐based systems, and transparent polymers are obtained upon visible‐light irradiation. The chemical mechanisms are also presented for a better understanding of their reactivity.</description><identifier>ISSN: 1022-1336</identifier><identifier>EISSN: 1521-3927</identifier><identifier>DOI: 10.1002/marc.201900319</identifier><identifier>PMID: 31486192</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>1‐aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones ; Aromatic compounds ; Bleaching ; blue light ; Ethane ; Ethane - chemistry ; Fourier transforms ; Free radical polymerization ; Free radicals ; green light ; Infrared spectroscopy ; Irradiation ; Light ; Light irradiation ; Methacrylates - chemical synthesis ; Methacrylates - chemistry ; Molecular orbitals ; Photoinitiators ; Polymerization ; Polymers ; Spectrophotometry, Ultraviolet</subject><ispartof>Macromolecular rapid communications., 2019-10, Vol.40 (20), p.e1900319-n/a</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-c4109-b57ce5d723bee2bafc3e4a37e92f6fd5f2659cdf53fbffc4ae16a54b164d034b3</citedby><cites>FETCH-LOGICAL-c4109-b57ce5d723bee2bafc3e4a37e92f6fd5f2659cdf53fbffc4ae16a54b164d034b3</cites><orcidid>0000-0001-9297-0335</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%2Fmarc.201900319$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fmarc.201900319$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,782,786,1419,27931,27932,45581,45582</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31486192$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kirschner, Julie</creatorcontrib><creatorcontrib>Baralle, Alexandre</creatorcontrib><creatorcontrib>Graff, Bernadette</creatorcontrib><creatorcontrib>Becht, Jean‐Michel</creatorcontrib><creatorcontrib>Klee, Joachim E.</creatorcontrib><creatorcontrib>Lalevée, Jacques</creatorcontrib><title>1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones: Toward a New Class of Visible Type I Photoinitiators for Free Radical Polymerization of Methacrylates</title><title>Macromolecular rapid communications.</title><addtitle>Macromol Rapid Commun</addtitle><description>1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones (SEDs) are proposed here as a new class of visible Type I photoinitiators (PIs) for free radical polymerization under air upon exposure to blue (@455 nm) and green (@520 nm) LEDs. Remarkably, these new systems present good polymerization performances and excellent bleaching properties compared to camphorquinone‐based systems, and transparent polymers are obtained upon visible light irradiation. Real‐time Fourier transform infrared spectroscopy is used to monitor the polymerization profiles. Molecular orbital calculations are also carried out for a better understanding of the structure/reactivity relationship of the photoinitiators.
1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones are presented here as a new class of visible Type I photoinitiators for free radical polymerization. These new systems present good polymerization performances and excellent bleaching properties compared to camphorquinone‐based systems, and transparent polymers are obtained upon visible‐light irradiation. The chemical mechanisms are also presented for a better understanding of their reactivity.</description><subject>1‐aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones</subject><subject>Aromatic compounds</subject><subject>Bleaching</subject><subject>blue light</subject><subject>Ethane</subject><subject>Ethane - chemistry</subject><subject>Fourier transforms</subject><subject>Free radical polymerization</subject><subject>Free radicals</subject><subject>green light</subject><subject>Infrared spectroscopy</subject><subject>Irradiation</subject><subject>Light</subject><subject>Light irradiation</subject><subject>Methacrylates - chemical synthesis</subject><subject>Methacrylates - chemistry</subject><subject>Molecular orbitals</subject><subject>Photoinitiators</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>1022-1336</issn><issn>1521-3927</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9uEzEQhy1ERUvhyhFZ4lKkbvD4zybmFkW0VGqhqgLXldc7Vl05cbA3ipYTj8AT8HA8CV6lLRIXDtZY8udvZvQj5BWwCTDG361MshPOQDMmQD8hR6A4VELz6dNyZ5xXIER9SJ7nfMcYm0nGn5FDAXJWg-ZH5Bf8_vFznoZQCi_npE_e57hJcTOE7MMQ3mJ_a9ZY3uB0JDof15jf02XcmdRRQz_hji6CyZlGR7_67NuAdDlskF7Q69vYR7_2vTd9TJm6mOhZQqQ3pvPWBHodw7DC5L-bvnhHw9XYz5aJTI_5BTlwJmR8eV-PyZezD8vFx-ry8_nFYn5ZWQlMV62aWlTdlIsWkbfGWYHSiClq7mrXKcdrpW3nlHCtc1YahNoo2UItOyZkK47Jyd5bFv-2xdw3K58thlA2j9vccD5TwFQNsqBv_kHv4jaty3QNF6yWAqDWhZrsKZtizglds0m-hDU0wJoxuWZMrnlMrnx4fa_dtivsHvGHqAqg98DOBxz-o2uu5jeLv_I_jPCsQw</recordid><startdate>201910</startdate><enddate>201910</enddate><creator>Kirschner, Julie</creator><creator>Baralle, Alexandre</creator><creator>Graff, Bernadette</creator><creator>Becht, Jean‐Michel</creator><creator>Klee, Joachim E.</creator><creator>Lalevée, Jacques</creator><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8FD</scope><scope>JG9</scope><scope>JQ2</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9297-0335</orcidid></search><sort><creationdate>201910</creationdate><title>1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones: Toward a New Class of Visible Type I Photoinitiators for Free Radical Polymerization of Methacrylates</title><author>Kirschner, Julie ; Baralle, Alexandre ; Graff, Bernadette ; Becht, Jean‐Michel ; Klee, Joachim E. ; Lalevée, Jacques</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4109-b57ce5d723bee2bafc3e4a37e92f6fd5f2659cdf53fbffc4ae16a54b164d034b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>1‐aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones</topic><topic>Aromatic compounds</topic><topic>Bleaching</topic><topic>blue light</topic><topic>Ethane</topic><topic>Ethane - chemistry</topic><topic>Fourier transforms</topic><topic>Free radical polymerization</topic><topic>Free radicals</topic><topic>green light</topic><topic>Infrared spectroscopy</topic><topic>Irradiation</topic><topic>Light</topic><topic>Light irradiation</topic><topic>Methacrylates - chemical synthesis</topic><topic>Methacrylates - chemistry</topic><topic>Molecular orbitals</topic><topic>Photoinitiators</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kirschner, Julie</creatorcontrib><creatorcontrib>Baralle, Alexandre</creatorcontrib><creatorcontrib>Graff, Bernadette</creatorcontrib><creatorcontrib>Becht, Jean‐Michel</creatorcontrib><creatorcontrib>Klee, Joachim E.</creatorcontrib><creatorcontrib>Lalevée, Jacques</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Macromolecular rapid communications.</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kirschner, Julie</au><au>Baralle, Alexandre</au><au>Graff, Bernadette</au><au>Becht, Jean‐Michel</au><au>Klee, Joachim E.</au><au>Lalevée, Jacques</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones: Toward a New Class of Visible Type I Photoinitiators for Free Radical Polymerization of Methacrylates</atitle><jtitle>Macromolecular rapid communications.</jtitle><addtitle>Macromol Rapid Commun</addtitle><date>2019-10</date><risdate>2019</risdate><volume>40</volume><issue>20</issue><spage>e1900319</spage><epage>n/a</epage><pages>e1900319-n/a</pages><issn>1022-1336</issn><eissn>1521-3927</eissn><abstract>1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones (SEDs) are proposed here as a new class of visible Type I photoinitiators (PIs) for free radical polymerization under air upon exposure to blue (@455 nm) and green (@520 nm) LEDs. Remarkably, these new systems present good polymerization performances and excellent bleaching properties compared to camphorquinone‐based systems, and transparent polymers are obtained upon visible light irradiation. Real‐time Fourier transform infrared spectroscopy is used to monitor the polymerization profiles. Molecular orbital calculations are also carried out for a better understanding of the structure/reactivity relationship of the photoinitiators.
1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones are presented here as a new class of visible Type I photoinitiators for free radical polymerization. These new systems present good polymerization performances and excellent bleaching properties compared to camphorquinone‐based systems, and transparent polymers are obtained upon visible‐light irradiation. The chemical mechanisms are also presented for a better understanding of their reactivity.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31486192</pmid><doi>10.1002/marc.201900319</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-9297-0335</orcidid></addata></record> |
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| subjects | 1‐aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones Aromatic compounds Bleaching blue light Ethane Ethane - chemistry Fourier transforms Free radical polymerization Free radicals green light Infrared spectroscopy Irradiation Light Light irradiation Methacrylates - chemical synthesis Methacrylates - chemistry Molecular orbitals Photoinitiators Polymerization Polymers Spectrophotometry, Ultraviolet |
| title | 1‐Aryl‐2‐(triisopropylsilyl)ethane‐1,2‐diones: Toward a New Class of Visible Type I Photoinitiators for Free Radical Polymerization of Methacrylates |
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