Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials
New liquid triarylamine–siloxane hybrid materials are produced using the Piers–Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of...
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| Veröffentlicht in: | Journal of organic chemistry 2012-02, Vol.77 (4), p.1663-1674 |
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| container_end_page | 1674 |
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| container_issue | 4 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Kamino, Brett A Mills, Bridget Reali, Christopher Gretton, Michael J Brook, Michael A Bender, Timothy P |
| description | New liquid triarylamine–siloxane hybrid materials are produced using the Piers–Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV–vis–NIR and 19F NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers–Rubinsztajn reaction. |
| doi_str_mv | 10.1021/jo2020906 |
| format | Article |
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Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV–vis–NIR and 19F NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. 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Org. Chem</addtitle><description>New liquid triarylamine–siloxane hybrid materials are produced using the Piers–Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV–vis–NIR and 19F NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers–Rubinsztajn reaction.</description><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Electrochemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Kinetics and mechanisms</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Si derivatives</subject><subject>Theory of reactions, general kinetics. Catalysis. 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Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamino, Brett A</creatorcontrib><creatorcontrib>Mills, Bridget</creatorcontrib><creatorcontrib>Reali, Christopher</creatorcontrib><creatorcontrib>Gretton, Michael J</creatorcontrib><creatorcontrib>Brook, Michael A</creatorcontrib><creatorcontrib>Bender, Timothy P</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kamino, Brett A</au><au>Mills, Bridget</au><au>Reali, Christopher</au><au>Gretton, Michael J</au><au>Brook, Michael A</au><au>Bender, Timothy P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-02-17</date><risdate>2012</risdate><volume>77</volume><issue>4</issue><spage>1663</spage><epage>1674</epage><pages>1663-1674</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>New liquid triarylamine–siloxane hybrid materials are produced using the Piers–Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV–vis–NIR and 19F NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers–Rubinsztajn reaction.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22220839</pmid><doi>10.1021/jo2020906</doi><tpages>12</tpages></addata></record> |
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| subjects | Catalysis Catalysts: preparations and properties Chemistry Electrochemistry Exact sciences and technology General and physical chemistry Kinetics and mechanisms Organic chemistry Organometalloidal and organometallic compounds Preparations and properties Reactivity and mechanisms Si derivatives Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials |
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