Tetraacylgermanes: Highly Efficient Photoinitiators for Visible‐Light‐Induced Free‐Radical Polymerization
In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R]4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge‐based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one‐pot synthetic protocol in >85 % yield...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-03, Vol.56 (11), p.3103-3107 |
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| creator | Radebner, Judith Eibel, Anna Leypold, Mario Gorsche, Christian Schuh, Lukas Fischer, Roland Torvisco, Ana Neshchadin, Dmytro Geier, Roman Moszner, Norbert Liska, Robert Gescheidt, Georg Haas, Michael Stueger, Harald |
| description | In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R]4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge‐based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one‐pot synthetic protocol in >85 % yield, as confirmed by NMR spectroscopy, mass spectrometry, and X‐ray crystallography. The efficiency of 1 a,b as photoinitiators is demonstrated in photobleaching (UV/Vis), time‐resolved EPR (CIDEP), and NMR/CIDNP investigations as well as by photo‐DSC studies. Remarkably, the tetraacylgermanes exceed the performance of currently known long‐wavelength visible‐light photoinitiators for free‐radical polymerization
“Molar” solutions: Germanium‐based photoinitiators for light‐induced radical polymerization outperform the established initiator systems, especially for applications in the long‐wavelength range, of particular interest in the dental industry. |
| doi_str_mv | 10.1002/anie.201611686 |
| format | Article |
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“Molar” solutions: Germanium‐based photoinitiators for light‐induced radical polymerization outperform the established initiator systems, especially for applications in the long‐wavelength range, of particular interest in the dental industry.</description><subject>acylgermanes</subject><subject>Crystallography</subject><subject>Free radicals</subject><subject>Light effects</subject><subject>Magnetic resonance spectroscopy</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>NMR</subject><subject>NMR spectroscopy</subject><subject>Nuclear magnetic resonance</subject><subject>Photobleaching</subject><subject>photochemistry</subject><subject>Photoinitiators</subject><subject>Polymerization</subject><subject>radical polymerization</subject><subject>reaction mechanisms</subject><subject>X-ray crystallography</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkc9u1DAQxi0EoqVw5YgiceGSxf_X4VZVW7rSCipUuFqOPW5dOXGxE6Fw4hF4Rp4Er7YUiQunGY1-82nm-xB6SfCKYEzfmjHAimIiCZFKPkLHRFDSsvWaPa49Z6xdK0GO0LNSbiuvFJZP0RFVREjM2TFKVzBlY-wSryEPZoTyrrkI1zdxaTbeBxtgnJrLmzSlMIYpmCnl0viUmy-hhD7Crx8_dxWfat2ObrbgmvMM-_En44I1sblMcRkgh-9mCml8jp54Ewu8uK8n6PP55ursot19fL89O921lhMsW-M7JojgHaHC4l5xhzsQ3jFvBAC1PfVSKOecB-YpZp3l3pjeSON7LnvMTtCbg-5dTl9nKJMeQrEQY30xzUUTJYXglCtV0df_oLdpzmO9TpNOVvu4XJNKrQ6UzamUDF7f5TCYvGiC9T4KvY9CP0RRF17dy879AO4B_-N9BboD8C1EWP4jp08_bDd_xX8DyFqaqg</recordid><startdate>20170306</startdate><enddate>20170306</enddate><creator>Radebner, Judith</creator><creator>Eibel, Anna</creator><creator>Leypold, Mario</creator><creator>Gorsche, Christian</creator><creator>Schuh, Lukas</creator><creator>Fischer, Roland</creator><creator>Torvisco, Ana</creator><creator>Neshchadin, Dmytro</creator><creator>Geier, Roman</creator><creator>Moszner, Norbert</creator><creator>Liska, Robert</creator><creator>Gescheidt, Georg</creator><creator>Haas, Michael</creator><creator>Stueger, Harald</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/0000-0001-8531-1964</orcidid></search><sort><creationdate>20170306</creationdate><title>Tetraacylgermanes: Highly Efficient Photoinitiators for Visible‐Light‐Induced Free‐Radical Polymerization</title><author>Radebner, Judith ; Eibel, Anna ; Leypold, Mario ; Gorsche, Christian ; Schuh, Lukas ; Fischer, Roland ; Torvisco, Ana ; Neshchadin, Dmytro ; Geier, Roman ; Moszner, Norbert ; Liska, Robert ; Gescheidt, Georg ; Haas, Michael ; Stueger, Harald</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4106-af9351549125c0b84d09e5fd3fa5ee2cb2f658dddfe3f2039c4faaba6afb46b03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>acylgermanes</topic><topic>Crystallography</topic><topic>Free radicals</topic><topic>Light effects</topic><topic>Magnetic resonance spectroscopy</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>NMR</topic><topic>NMR spectroscopy</topic><topic>Nuclear magnetic resonance</topic><topic>Photobleaching</topic><topic>photochemistry</topic><topic>Photoinitiators</topic><topic>Polymerization</topic><topic>radical polymerization</topic><topic>reaction mechanisms</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Radebner, Judith</creatorcontrib><creatorcontrib>Eibel, Anna</creatorcontrib><creatorcontrib>Leypold, Mario</creatorcontrib><creatorcontrib>Gorsche, Christian</creatorcontrib><creatorcontrib>Schuh, Lukas</creatorcontrib><creatorcontrib>Fischer, Roland</creatorcontrib><creatorcontrib>Torvisco, Ana</creatorcontrib><creatorcontrib>Neshchadin, Dmytro</creatorcontrib><creatorcontrib>Geier, Roman</creatorcontrib><creatorcontrib>Moszner, Norbert</creatorcontrib><creatorcontrib>Liska, Robert</creatorcontrib><creatorcontrib>Gescheidt, Georg</creatorcontrib><creatorcontrib>Haas, Michael</creatorcontrib><creatorcontrib>Stueger, Harald</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>Radebner, Judith</au><au>Eibel, Anna</au><au>Leypold, Mario</au><au>Gorsche, Christian</au><au>Schuh, Lukas</au><au>Fischer, Roland</au><au>Torvisco, Ana</au><au>Neshchadin, Dmytro</au><au>Geier, Roman</au><au>Moszner, Norbert</au><au>Liska, Robert</au><au>Gescheidt, Georg</au><au>Haas, Michael</au><au>Stueger, Harald</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tetraacylgermanes: Highly Efficient Photoinitiators for Visible‐Light‐Induced Free‐Radical Polymerization</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-03-06</date><risdate>2017</risdate><volume>56</volume><issue>11</issue><spage>3103</spage><epage>3107</epage><pages>3103-3107</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R]4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge‐based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one‐pot synthetic protocol in >85 % yield, as confirmed by NMR spectroscopy, mass spectrometry, and X‐ray crystallography. The efficiency of 1 a,b as photoinitiators is demonstrated in photobleaching (UV/Vis), time‐resolved EPR (CIDEP), and NMR/CIDNP investigations as well as by photo‐DSC studies. Remarkably, the tetraacylgermanes exceed the performance of currently known long‐wavelength visible‐light photoinitiators for free‐radical polymerization
“Molar” solutions: Germanium‐based photoinitiators for light‐induced radical polymerization outperform the established initiator systems, especially for applications in the long‐wavelength range, of particular interest in the dental industry.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28156043</pmid><doi>10.1002/anie.201611686</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-8531-1964</orcidid></addata></record> |
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| subjects | acylgermanes Crystallography Free radicals Light effects Magnetic resonance spectroscopy Mass spectrometry Mass spectroscopy NMR NMR spectroscopy Nuclear magnetic resonance Photobleaching photochemistry Photoinitiators Polymerization radical polymerization reaction mechanisms X-ray crystallography |
| title | Tetraacylgermanes: Highly Efficient Photoinitiators for Visible‐Light‐Induced Free‐Radical Polymerization |
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