Investigation of an electrochemically switched heterocyclization reaction on gold surface

We report an investigation of an electrochemically switched heterocyclization reaction on hydroquinone-terminated self-assembled monolayers (SAMs). This reaction involves an electrochemically modulated hydroquinone/benzoquinone transformation step in the SAMs and a subsequent heterocyclization step...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 29(2013), 17 vom: 30. Apr., Seite 5199-206
1. Verfasser: Li, Jun (VerfasserIn)
Weitere Verfasser: Sun, Chun-Lin, Tan, Lin, Xie, Yu-Long, Zhang, Hao-Li
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2013
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article Research Support, Non-U.S. Gov't Benzoquinones Hydroquinones quinone 3T006GV98U Gold 7440-57-5 Cysteine K848JZ4886 mehr... hydroquinone XV74C1N1AE
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520 |a We report an investigation of an electrochemically switched heterocyclization reaction on hydroquinone-terminated self-assembled monolayers (SAMs). This reaction involves an electrochemically modulated hydroquinone/benzoquinone transformation step in the SAMs and a subsequent heterocyclization step taking place between the electrochemically generated benzoquinone moieties in SAMs and l-cysteine in solution. The reaction process was monitored by XPS and electrochemical surface-enhanced Raman spectroscopy (EC-SERS). The surface reaction proceeds as a two-step reaction to give a benzothiazine product, which is in contrast to the much more complicated multiple step reactions in solution. This result suggests that the tight molecular packing in the SAMs does not hinder the intramolecular heterocylization reaction, but prevents the intermolecular coupling reaction from happening. This work provides insights to the control and detection of biomolecule related multistep reactions occurring at solid-liquid interface 
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650 4 |a Research Support, Non-U.S. Gov't 
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700 1 |a Sun, Chun-Lin  |e verfasserin  |4 aut 
700 1 |a Tan, Lin  |e verfasserin  |4 aut 
700 1 |a Xie, Yu-Long  |e verfasserin  |4 aut 
700 1 |a Zhang, Hao-Li  |e verfasserin  |4 aut 
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