title: Investigation of an electrochemically switched heterocyclization reaction on gold surface.
abstract: 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.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui South Road, Lanzhou, 730000, People's Republic of China.
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Chun-Lin
authors.initials: CL
authors.lastname: Sun
authors.forename: Lin
authors.initials: L
authors.lastname: Tan
authors.forename: Yu-Long
authors.initials: YL
authors.lastname: Xie
authors.forename: Hao-Li
authors.initials: HL
authors.lastname: Zhang
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D003500:Cyclization; D003545:Cysteine / Q000737:chemistry*; D055664:Electrochemical Techniques; D006046:Gold / Q000737:chemistry*; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013499:Surface Properties
chemical_list: D016227:Benzoquinones; D006873:Hydroquinones; C004532:quinone; D006046:Gold; D003545:Cysteine; C031927:hydroquinone