Mediated electrochemical reduction of oxygen to hydrogen peroxide via a surface-confined naphthoquinone reagent and the mediated electrochemical reduction of a naphthoquinone redox reagent anchored to high surface area oxides
Derivatives of 1,4-naphthoquinone, 2-chloro-3-((2-(dimethylpropylammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ia, and 2-chloro-3-((2-(dimethyl(3-(trimethoxysilyl)propyl)ammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ib, have been synthesized and used as solution and surface-bound catalysts, re...
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| Veröffentlicht in: | J. Am. Chem. Soc.; (United States) 1983-08, Vol.105 (17), p.5594-5600 |
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| creator | Calabrese, Gary S Buchanan, Robert M Wrighton, Mark S |
| description | Derivatives of 1,4-naphthoquinone, 2-chloro-3-((2-(dimethylpropylammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ia, and 2-chloro-3-((2-(dimethyl(3-(trimethoxysilyl)propyl)ammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ib, have been synthesized and used as solution and surface-bound catalysts, respectively, for the electrochemical and photoelectrochemical reduction of O/sub 2/ to H/sub 2/O/sub 2/. The surface derivatizing reagent Ib having the -Si(OCH/sub 3/)/sub 3/ functionality can be used to functionalize a variety of surfaces including electrode materials and high surface area oxides. The surface reagent, (Q/QH/sub 2/)/sub surf/, has the same E/sup 0/' as Ia in solution, approx. -0.4 V vs. SCE at pH 7. The (QH/sub 2/)/sub surf/ reacts with O/sub 2/ in aqueous electrolyte at pH 7 with a rate constant > 10/sup 5/ M/sup -1/s/sup -1/ to form H/sub 2/O/sub 2/ and (Q)/sub surf/. High surface area oxides functionalized with Ib yield (M/sub x/O/sub y/)-(Q) that can be electrochemically reduced to (M/sub x/O/sub y/)-(QH/sub 2/) via mediation by a low concentration of Ia in solution. The (M/sub x/O/sub y/)-(QH/sub 2/) can be isolated from the electrolyte solution by filtration and reacted with O/sub 2//H/sub 2/O to yield up to 0.1 M H/sub 2/O/sub 2/ in H/sub 2/O free of electrolyte. Study of the reduction of Ia at rotating-W-disk electrodes derivatized with Ib shows that the redox equilibration of the solution quinone and surface quinone is rapid. Reduction of (Q)/sub surf/ or Ia at visible light illuminated p-WS/sub 2/ can be effected at an electrode potential approx. 0.8 V more positive than at a metallic electode. The overall energetics are such that light can be used to effect the uphill formation of H/sub 2/O/sub 2/ via the quinone-mediated reduction of O/sub 2/. The onset of O/sub 2/ reduction is up to 0.6 V more positive than E/sup 0/'(O/sub 2//H/sub 2/O/sub 2/). The sustained photoassisted reduction of O/sub 2/ to H/sub 2/O/sub 2/ has been demonstrated. 15 references, 8 figures, 2 tables. |
| doi_str_mv | 10.1021/ja00355a011 |
| format | Article |
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The surface derivatizing reagent Ib having the -Si(OCH/sub 3/)/sub 3/ functionality can be used to functionalize a variety of surfaces including electrode materials and high surface area oxides. The surface reagent, (Q/QH/sub 2/)/sub surf/, has the same E/sup 0/' as Ia in solution, approx. -0.4 V vs. SCE at pH 7. The (QH/sub 2/)/sub surf/ reacts with O/sub 2/ in aqueous electrolyte at pH 7 with a rate constant > 10/sup 5/ M/sup -1/s/sup -1/ to form H/sub 2/O/sub 2/ and (Q)/sub surf/. High surface area oxides functionalized with Ib yield (M/sub x/O/sub y/)-(Q) that can be electrochemically reduced to (M/sub x/O/sub y/)-(QH/sub 2/) via mediation by a low concentration of Ia in solution. The (M/sub x/O/sub y/)-(QH/sub 2/) can be isolated from the electrolyte solution by filtration and reacted with O/sub 2//H/sub 2/O to yield up to 0.1 M H/sub 2/O/sub 2/ in H/sub 2/O free of electrolyte. Study of the reduction of Ia at rotating-W-disk electrodes derivatized with Ib shows that the redox equilibration of the solution quinone and surface quinone is rapid. Reduction of (Q)/sub surf/ or Ia at visible light illuminated p-WS/sub 2/ can be effected at an electrode potential approx. 0.8 V more positive than at a metallic electode. The overall energetics are such that light can be used to effect the uphill formation of H/sub 2/O/sub 2/ via the quinone-mediated reduction of O/sub 2/. The onset of O/sub 2/ reduction is up to 0.6 V more positive than E/sup 0/'(O/sub 2//H/sub 2/O/sub 2/). The sustained photoassisted reduction of O/sub 2/ to H/sub 2/O/sub 2/ has been demonstrated. 15 references, 8 figures, 2 tables.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja00355a011</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>400400 - Electrochemistry ; 400500 - Photochemistry ; AROMATICS ; BENZOQUINONES ; CHEMICAL REACTIONS ; CHEMISTRY ; DERIVATIZATION ; ELECTROCHEMISTRY ; ELEMENTS ; HYDROGEN COMPOUNDS ; HYDROGEN PEROXIDE ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; NONMETALS ; ORGANIC COMPOUNDS ; ORGANIC OXYGEN COMPOUNDS ; OXYGEN ; OXYGEN COMPOUNDS ; PEROXIDES ; PHOTOCHEMICAL REACTIONS ; QUINONES ; REDOX POTENTIAL ; REDUCTION ; SYNTHESIS</subject><ispartof>J. Am. Chem. Soc.; (United States), 1983-08, Vol.105 (17), p.5594-5600</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a394t-5fb65879bc368267756835764c4c8e3c7975544a35484449ebfbf76ee05a708d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja00355a011$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja00355a011$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.osti.gov/biblio/5510530$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Calabrese, Gary S</creatorcontrib><creatorcontrib>Buchanan, Robert M</creatorcontrib><creatorcontrib>Wrighton, Mark S</creatorcontrib><creatorcontrib>Massachusetts Inst. of Tech., Cambridge</creatorcontrib><title>Mediated electrochemical reduction of oxygen to hydrogen peroxide via a surface-confined naphthoquinone reagent and the mediated electrochemical reduction of a naphthoquinone redox reagent anchored to high surface area oxides</title><title>J. Am. Chem. Soc.; (United States)</title><addtitle>J. Am. Chem. Soc</addtitle><description>Derivatives of 1,4-naphthoquinone, 2-chloro-3-((2-(dimethylpropylammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ia, and 2-chloro-3-((2-(dimethyl(3-(trimethoxysilyl)propyl)ammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ib, have been synthesized and used as solution and surface-bound catalysts, respectively, for the electrochemical and photoelectrochemical reduction of O/sub 2/ to H/sub 2/O/sub 2/. The surface derivatizing reagent Ib having the -Si(OCH/sub 3/)/sub 3/ functionality can be used to functionalize a variety of surfaces including electrode materials and high surface area oxides. The surface reagent, (Q/QH/sub 2/)/sub surf/, has the same E/sup 0/' as Ia in solution, approx. -0.4 V vs. SCE at pH 7. The (QH/sub 2/)/sub surf/ reacts with O/sub 2/ in aqueous electrolyte at pH 7 with a rate constant > 10/sup 5/ M/sup -1/s/sup -1/ to form H/sub 2/O/sub 2/ and (Q)/sub surf/. High surface area oxides functionalized with Ib yield (M/sub x/O/sub y/)-(Q) that can be electrochemically reduced to (M/sub x/O/sub y/)-(QH/sub 2/) via mediation by a low concentration of Ia in solution. The (M/sub x/O/sub y/)-(QH/sub 2/) can be isolated from the electrolyte solution by filtration and reacted with O/sub 2//H/sub 2/O to yield up to 0.1 M H/sub 2/O/sub 2/ in H/sub 2/O free of electrolyte. Study of the reduction of Ia at rotating-W-disk electrodes derivatized with Ib shows that the redox equilibration of the solution quinone and surface quinone is rapid. Reduction of (Q)/sub surf/ or Ia at visible light illuminated p-WS/sub 2/ can be effected at an electrode potential approx. 0.8 V more positive than at a metallic electode. The overall energetics are such that light can be used to effect the uphill formation of H/sub 2/O/sub 2/ via the quinone-mediated reduction of O/sub 2/. The onset of O/sub 2/ reduction is up to 0.6 V more positive than E/sup 0/'(O/sub 2//H/sub 2/O/sub 2/). The sustained photoassisted reduction of O/sub 2/ to H/sub 2/O/sub 2/ has been demonstrated. 15 references, 8 figures, 2 tables.</description><subject>400400 - Electrochemistry</subject><subject>400500 - Photochemistry</subject><subject>AROMATICS</subject><subject>BENZOQUINONES</subject><subject>CHEMICAL REACTIONS</subject><subject>CHEMISTRY</subject><subject>DERIVATIZATION</subject><subject>ELECTROCHEMISTRY</subject><subject>ELEMENTS</subject><subject>HYDROGEN COMPOUNDS</subject><subject>HYDROGEN PEROXIDE</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>NONMETALS</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC OXYGEN COMPOUNDS</subject><subject>OXYGEN</subject><subject>OXYGEN COMPOUNDS</subject><subject>PEROXIDES</subject><subject>PHOTOCHEMICAL REACTIONS</subject><subject>QUINONES</subject><subject>REDOX POTENTIAL</subject><subject>REDUCTION</subject><subject>SYNTHESIS</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><recordid>eNqNkctuUzEQhi0EEqGw4gUsNizQKfbxNUtUUYrUikoEsbQmPnN6HBI72E6VPC5vgtsAqgQLVr7o8zf_eAh5ydkpZz1_uwLGhFLAOH9EZlz1rFO814_JjDHWd8Zq8ZQ8K2XVjrK3fEZ-XOEQoOJAcY2-5uQn3AQPa5px2PkaUqRppGl_uMFIa6LTYcjpbr_FnPZhQHobgAItuzyCx86nOIbYfBG2U53S912IKWLTQXtVKcSB1gnp5r_qwt-aIe0fyPyU2tV9sHAz_U5BoRH0Pl55Tp6MsC744td6Qr6cv1-cXXSXnz58PHt32YGYy9qpcamVNfOlF9r22hilrVBGSy-9ReHN3CglJQglrZRyjstxORqNyBQYZgdxQl4dvanU4IoPFf3UfiO29pxSnCnBGvTmCPmcSsk4um0OG8gHx5m7G6F7MMJGd0c6lIr7Pyjkb04bYZRbXH927OJ88ZVZ7a4b__rIgy9ulXY5tob_af4Ji1yv7w</recordid><startdate>198308</startdate><enddate>198308</enddate><creator>Calabrese, Gary S</creator><creator>Buchanan, Robert M</creator><creator>Wrighton, Mark S</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>198308</creationdate><title>Mediated electrochemical reduction of oxygen to hydrogen peroxide via a surface-confined naphthoquinone reagent and the mediated electrochemical reduction of a naphthoquinone redox reagent anchored to high surface area oxides</title><author>Calabrese, Gary S ; Buchanan, Robert M ; Wrighton, Mark S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a394t-5fb65879bc368267756835764c4c8e3c7975544a35484449ebfbf76ee05a708d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>400400 - Electrochemistry</topic><topic>400500 - Photochemistry</topic><topic>AROMATICS</topic><topic>BENZOQUINONES</topic><topic>CHEMICAL REACTIONS</topic><topic>CHEMISTRY</topic><topic>DERIVATIZATION</topic><topic>ELECTROCHEMISTRY</topic><topic>ELEMENTS</topic><topic>HYDROGEN COMPOUNDS</topic><topic>HYDROGEN PEROXIDE</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>NONMETALS</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC OXYGEN COMPOUNDS</topic><topic>OXYGEN</topic><topic>OXYGEN COMPOUNDS</topic><topic>PEROXIDES</topic><topic>PHOTOCHEMICAL REACTIONS</topic><topic>QUINONES</topic><topic>REDOX POTENTIAL</topic><topic>REDUCTION</topic><topic>SYNTHESIS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Calabrese, Gary S</creatorcontrib><creatorcontrib>Buchanan, Robert M</creatorcontrib><creatorcontrib>Wrighton, Mark S</creatorcontrib><creatorcontrib>Massachusetts Inst. of Tech., Cambridge</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>J. Am. Chem. Soc.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Calabrese, Gary S</au><au>Buchanan, Robert M</au><au>Wrighton, Mark S</au><aucorp>Massachusetts Inst. of Tech., Cambridge</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mediated electrochemical reduction of oxygen to hydrogen peroxide via a surface-confined naphthoquinone reagent and the mediated electrochemical reduction of a naphthoquinone redox reagent anchored to high surface area oxides</atitle><jtitle>J. Am. Chem. Soc.; (United States)</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>1983-08</date><risdate>1983</risdate><volume>105</volume><issue>17</issue><spage>5594</spage><epage>5600</epage><pages>5594-5600</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Derivatives of 1,4-naphthoquinone, 2-chloro-3-((2-(dimethylpropylammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ia, and 2-chloro-3-((2-(dimethyl(3-(trimethoxysilyl)propyl)ammonio)ethyl)amino)-1,4-naphthoquinone bromide, Ib, have been synthesized and used as solution and surface-bound catalysts, respectively, for the electrochemical and photoelectrochemical reduction of O/sub 2/ to H/sub 2/O/sub 2/. The surface derivatizing reagent Ib having the -Si(OCH/sub 3/)/sub 3/ functionality can be used to functionalize a variety of surfaces including electrode materials and high surface area oxides. The surface reagent, (Q/QH/sub 2/)/sub surf/, has the same E/sup 0/' as Ia in solution, approx. -0.4 V vs. SCE at pH 7. The (QH/sub 2/)/sub surf/ reacts with O/sub 2/ in aqueous electrolyte at pH 7 with a rate constant > 10/sup 5/ M/sup -1/s/sup -1/ to form H/sub 2/O/sub 2/ and (Q)/sub surf/. High surface area oxides functionalized with Ib yield (M/sub x/O/sub y/)-(Q) that can be electrochemically reduced to (M/sub x/O/sub y/)-(QH/sub 2/) via mediation by a low concentration of Ia in solution. The (M/sub x/O/sub y/)-(QH/sub 2/) can be isolated from the electrolyte solution by filtration and reacted with O/sub 2//H/sub 2/O to yield up to 0.1 M H/sub 2/O/sub 2/ in H/sub 2/O free of electrolyte. Study of the reduction of Ia at rotating-W-disk electrodes derivatized with Ib shows that the redox equilibration of the solution quinone and surface quinone is rapid. Reduction of (Q)/sub surf/ or Ia at visible light illuminated p-WS/sub 2/ can be effected at an electrode potential approx. 0.8 V more positive than at a metallic electode. The overall energetics are such that light can be used to effect the uphill formation of H/sub 2/O/sub 2/ via the quinone-mediated reduction of O/sub 2/. The onset of O/sub 2/ reduction is up to 0.6 V more positive than E/sup 0/'(O/sub 2//H/sub 2/O/sub 2/). The sustained photoassisted reduction of O/sub 2/ to H/sub 2/O/sub 2/ has been demonstrated. 15 references, 8 figures, 2 tables.</abstract><cop>United States</cop><pub>American Chemical Society</pub><doi>10.1021/ja00355a011</doi><tpages>7</tpages></addata></record> |
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| ispartof | J. Am. Chem. Soc.; (United States), 1983-08, Vol.105 (17), p.5594-5600 |
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| subjects | 400400 - Electrochemistry 400500 - Photochemistry AROMATICS BENZOQUINONES CHEMICAL REACTIONS CHEMISTRY DERIVATIZATION ELECTROCHEMISTRY ELEMENTS HYDROGEN COMPOUNDS HYDROGEN PEROXIDE INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY NONMETALS ORGANIC COMPOUNDS ORGANIC OXYGEN COMPOUNDS OXYGEN OXYGEN COMPOUNDS PEROXIDES PHOTOCHEMICAL REACTIONS QUINONES REDOX POTENTIAL REDUCTION SYNTHESIS |
| title | Mediated electrochemical reduction of oxygen to hydrogen peroxide via a surface-confined naphthoquinone reagent and the mediated electrochemical reduction of a naphthoquinone redox reagent anchored to high surface area oxides |
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