Symmetrical and Mixed Tris(acyl)phosphines: Synthesis, Oxidation and Photochemistry
Herein, we present a convenient synthesis for symmetrical and mixed substituted tris(acyl)phosphines (TAPs) starting from red phosphorus. All TAPs exhibit a phosphaalkene‐acylphosphine equilibrium, which was investigated in detail by variable‐temperature (VT) NMR spectroscopy supported by density‐fu...
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| Veröffentlicht in: | Chemistry : a European journal 2023-12, Vol.29 (67), p.e202302535-n/a |
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| creator | Wiesner, Tanja Neshchadin, Dmytro Glotz, Gabriel Gfader, Zeno Schrader, Erik Christen, Samuel Fischer, Roland C. Kelterer, Anne‐Marie Gescheidt, Georg Grützmacher, Hansjörg Haas, Michael |
| description | Herein, we present a convenient synthesis for symmetrical and mixed substituted tris(acyl)phosphines (TAPs) starting from red phosphorus. All TAPs exhibit a phosphaalkene‐acylphosphine equilibrium, which was investigated in detail by variable‐temperature (VT) NMR spectroscopy supported by density‐functional theory (DFT) calculations. Depending on the substituents, two phosphaalkene derivatives and ten acylphosphine derivatives could be isolated. NMR spectroscopy and single‐crystal X‐ray crystallography enabled a clear structural assignment of these compounds. Oxidation of selected TAPs led to the formation of the corresponding tris(acyl)phosphine oxides (TAPOs). Furthermore, their spectroscopic properties as well as their photochemistry was investigated. Especially, the TAPO compounds were evaluated for their suitability as photoinitiators by CIDNP spectroscopy, photobleaching measurements and by storage stability tests.
Symmetrical and mixed tris(acyl)phosphines: In this contribution, we present a convenient synthetic procedure starting from red phosphorus to tris(acyl)phosphines (TAPs) and moreover to tris(acyl)phosphine oxides (TAPOs). Several of the synthesized TAPs exhibit a phosphine‐phophaalkene equilibrium, which was studied in detail. The oxidation of some selected TAPs yielded the corresponding TAPOs, which were tested as potential photoinitiators for application. |
| doi_str_mv | 10.1002/chem.202302535 |
| format | Article |
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Symmetrical and mixed tris(acyl)phosphines: In this contribution, we present a convenient synthetic procedure starting from red phosphorus to tris(acyl)phosphines (TAPs) and moreover to tris(acyl)phosphine oxides (TAPOs). Several of the synthesized TAPs exhibit a phosphine‐phophaalkene equilibrium, which was studied in detail. The oxidation of some selected TAPs yielded the corresponding TAPOs, which were tested as potential photoinitiators for application.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202302535</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>acylphosphine oxides ; acylphosphines ; Chemistry ; Crystallography ; Density functional theory ; Magnetic resonance spectroscopy ; Mathematical analysis ; NMR ; NMR spectroscopy ; Nuclear magnetic resonance ; Oxidation ; phosphaalkenes ; Phosphine ; Phosphine oxide ; phosphorus ; Photobleaching ; Photochemistry ; Photoinitiators ; Spectroscopy ; Stability tests ; Storage stability ; Synthesis</subject><ispartof>Chemistry : a European journal, 2023-12, Vol.29 (67), p.e202302535-n/a</ispartof><rights>2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH</rights><rights>2023. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3455-57bbee243a1d254f12f66a1468c842db86bf7f6c6da4aec54af9f438e33441063</cites><orcidid>0000-0002-9213-940X</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%2Fchem.202302535$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202302535$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Wiesner, Tanja</creatorcontrib><creatorcontrib>Neshchadin, Dmytro</creatorcontrib><creatorcontrib>Glotz, Gabriel</creatorcontrib><creatorcontrib>Gfader, Zeno</creatorcontrib><creatorcontrib>Schrader, Erik</creatorcontrib><creatorcontrib>Christen, Samuel</creatorcontrib><creatorcontrib>Fischer, Roland C.</creatorcontrib><creatorcontrib>Kelterer, Anne‐Marie</creatorcontrib><creatorcontrib>Gescheidt, Georg</creatorcontrib><creatorcontrib>Grützmacher, Hansjörg</creatorcontrib><creatorcontrib>Haas, Michael</creatorcontrib><title>Symmetrical and Mixed Tris(acyl)phosphines: Synthesis, Oxidation and Photochemistry</title><title>Chemistry : a European journal</title><description>Herein, we present a convenient synthesis for symmetrical and mixed substituted tris(acyl)phosphines (TAPs) starting from red phosphorus. All TAPs exhibit a phosphaalkene‐acylphosphine equilibrium, which was investigated in detail by variable‐temperature (VT) NMR spectroscopy supported by density‐functional theory (DFT) calculations. Depending on the substituents, two phosphaalkene derivatives and ten acylphosphine derivatives could be isolated. NMR spectroscopy and single‐crystal X‐ray crystallography enabled a clear structural assignment of these compounds. Oxidation of selected TAPs led to the formation of the corresponding tris(acyl)phosphine oxides (TAPOs). Furthermore, their spectroscopic properties as well as their photochemistry was investigated. Especially, the TAPO compounds were evaluated for their suitability as photoinitiators by CIDNP spectroscopy, photobleaching measurements and by storage stability tests.
Symmetrical and mixed tris(acyl)phosphines: In this contribution, we present a convenient synthetic procedure starting from red phosphorus to tris(acyl)phosphines (TAPs) and moreover to tris(acyl)phosphine oxides (TAPOs). Several of the synthesized TAPs exhibit a phosphine‐phophaalkene equilibrium, which was studied in detail. The oxidation of some selected TAPs yielded the corresponding TAPOs, which were tested as potential photoinitiators for application.</description><subject>acylphosphine oxides</subject><subject>acylphosphines</subject><subject>Chemistry</subject><subject>Crystallography</subject><subject>Density functional theory</subject><subject>Magnetic resonance spectroscopy</subject><subject>Mathematical analysis</subject><subject>NMR</subject><subject>NMR spectroscopy</subject><subject>Nuclear magnetic resonance</subject><subject>Oxidation</subject><subject>phosphaalkenes</subject><subject>Phosphine</subject><subject>Phosphine oxide</subject><subject>phosphorus</subject><subject>Photobleaching</subject><subject>Photochemistry</subject><subject>Photoinitiators</subject><subject>Spectroscopy</subject><subject>Stability tests</subject><subject>Storage stability</subject><subject>Synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkM9LwzAYhoMoOKdXzwUvE-zM77beZEwnbEzYPIc0TWhG28ykw_W_t3Oi4MXTd3me7_2-F4BrBMcIQnyvSl2PMcQEYkbYCRgghlFMEs5OwQBmNIk5I9k5uAhhAyHMOCEDsFp1da1bb5WsItkU0cLudRGtvQ0jqbrqdlu6sC1to8NDtOqattTBhrtoubeFbK1rvqTX0rXukG9D67tLcGZkFfTV9xyCt6fpejKL58vnl8njPFaEMhazJM-1xpRIVGBGDcKGc4koT1VKcZGnPDeJ4YoXkkqtGJUmM5SkmhBKEeRkCEbHvVvv3nc6tKLPV7qqZKPdLgiccsoRzxjq0Zs_6MbtfNNf11MZ45hTQnpqfKSUdyF4bcTW21r6TiAoDh2Lw4_ip-NeyI7Ch6109w8tJrPp4tf9BJcegDc</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Wiesner, Tanja</creator><creator>Neshchadin, Dmytro</creator><creator>Glotz, Gabriel</creator><creator>Gfader, Zeno</creator><creator>Schrader, Erik</creator><creator>Christen, Samuel</creator><creator>Fischer, Roland C.</creator><creator>Kelterer, Anne‐Marie</creator><creator>Gescheidt, Georg</creator><creator>Grützmacher, Hansjörg</creator><creator>Haas, Michael</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9213-940X</orcidid></search><sort><creationdate>20231201</creationdate><title>Symmetrical and Mixed Tris(acyl)phosphines: Synthesis, Oxidation and Photochemistry</title><author>Wiesner, Tanja ; Neshchadin, Dmytro ; Glotz, Gabriel ; Gfader, Zeno ; Schrader, Erik ; Christen, Samuel ; Fischer, Roland C. ; Kelterer, Anne‐Marie ; Gescheidt, Georg ; Grützmacher, Hansjörg ; Haas, Michael</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3455-57bbee243a1d254f12f66a1468c842db86bf7f6c6da4aec54af9f438e33441063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>acylphosphine oxides</topic><topic>acylphosphines</topic><topic>Chemistry</topic><topic>Crystallography</topic><topic>Density functional theory</topic><topic>Magnetic resonance spectroscopy</topic><topic>Mathematical analysis</topic><topic>NMR</topic><topic>NMR spectroscopy</topic><topic>Nuclear magnetic resonance</topic><topic>Oxidation</topic><topic>phosphaalkenes</topic><topic>Phosphine</topic><topic>Phosphine oxide</topic><topic>phosphorus</topic><topic>Photobleaching</topic><topic>Photochemistry</topic><topic>Photoinitiators</topic><topic>Spectroscopy</topic><topic>Stability tests</topic><topic>Storage stability</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wiesner, Tanja</creatorcontrib><creatorcontrib>Neshchadin, Dmytro</creatorcontrib><creatorcontrib>Glotz, Gabriel</creatorcontrib><creatorcontrib>Gfader, Zeno</creatorcontrib><creatorcontrib>Schrader, Erik</creatorcontrib><creatorcontrib>Christen, Samuel</creatorcontrib><creatorcontrib>Fischer, Roland C.</creatorcontrib><creatorcontrib>Kelterer, Anne‐Marie</creatorcontrib><creatorcontrib>Gescheidt, Georg</creatorcontrib><creatorcontrib>Grützmacher, Hansjörg</creatorcontrib><creatorcontrib>Haas, Michael</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wiesner, Tanja</au><au>Neshchadin, Dmytro</au><au>Glotz, Gabriel</au><au>Gfader, Zeno</au><au>Schrader, Erik</au><au>Christen, Samuel</au><au>Fischer, Roland C.</au><au>Kelterer, Anne‐Marie</au><au>Gescheidt, Georg</au><au>Grützmacher, Hansjörg</au><au>Haas, Michael</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Symmetrical and Mixed Tris(acyl)phosphines: Synthesis, Oxidation and Photochemistry</atitle><jtitle>Chemistry : a European journal</jtitle><date>2023-12-01</date><risdate>2023</risdate><volume>29</volume><issue>67</issue><spage>e202302535</spage><epage>n/a</epage><pages>e202302535-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Herein, we present a convenient synthesis for symmetrical and mixed substituted tris(acyl)phosphines (TAPs) starting from red phosphorus. 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Symmetrical and mixed tris(acyl)phosphines: In this contribution, we present a convenient synthetic procedure starting from red phosphorus to tris(acyl)phosphines (TAPs) and moreover to tris(acyl)phosphine oxides (TAPOs). Several of the synthesized TAPs exhibit a phosphine‐phophaalkene equilibrium, which was studied in detail. The oxidation of some selected TAPs yielded the corresponding TAPOs, which were tested as potential photoinitiators for application.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/chem.202302535</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-9213-940X</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | acylphosphine oxides acylphosphines Chemistry Crystallography Density functional theory Magnetic resonance spectroscopy Mathematical analysis NMR NMR spectroscopy Nuclear magnetic resonance Oxidation phosphaalkenes Phosphine Phosphine oxide phosphorus Photobleaching Photochemistry Photoinitiators Spectroscopy Stability tests Storage stability Synthesis |
| title | Symmetrical and Mixed Tris(acyl)phosphines: Synthesis, Oxidation and Photochemistry |
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