对氨基硫酚在Au（111）上电化学氧化偶联过程中分子结构演变的原位扫描隧道显微镜可视化研究

doi:10.61558/2993-074X.3614

电化学（中英文） ›› 2026, Vol. 32 ›› Issue (7): 2603031. doi: 10.61558/2993-074X.3614

对氨基硫酚在Au（111）上电化学氧化偶联过程中分子结构演变的原位扫描隧道显微镜可视化研究

马子为^,^#, 吴泰锐^,^#, 郑安妮, 陈来科, 肖远辉, 陈招斌, 郑轻娜^*()(), 周剑章^*()(), 颜佳伟^*()(), 吴德印^*()()

厦门大学化学化工学院，表界面化学全国重点实验室，厦门 361005

收稿日期:2026-03-03 修回日期:2026-04-18 接受日期:2026-05-09 发布日期:2026-05-09 出版日期:2026-07-28

In-Situ STM Visualization of Molecular Structural Evolution during Electrochemical Oxidation Coupling of Para-Aminothiophenol on Au(111)

Zi-Wei Ma^,^#, Tai-Rui Wu^,^#, An-Ni Zheng, Lai-Ke Chen, Yuan-Hui Xiao, Zhao-Bin Chen, Qing-Na Zheng^*()(), Jian-Zhang Zhou^*()(), Jia-Wei Yan^*()(), De-Yin Wu^*()()

State Key Laboratory of Physical Chemistry of Solid Surface, and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China

Received:2026-03-03 Revised:2026-04-18 Accepted:2026-05-09 Online:2026-05-09 Published:2026-07-28
Contact: * E-mail addresses: zhengqn@xmu.edu.cn (Q-N Zheng),
jzzhou@xmu.edu.cn (J-Z Zhou),
jwyan@xmu.edu.cn (J-W Yan),
dywu@xmu.edu.cn (D-Y Wu).
About author:Author Contributions
Zi-Wei Ma and Tai-Rui Wu was responsible for the experimental design, implementation, data analysis, and writing of the original draft. An-Ni Zheng, Lai-Ke Chen, Yuan-Hui Xiao and Zhao-Bin Chen assisted in experimental implementation and data analysis. Qing-Na Zheng, Jian-Zhang Zhou, Jia-Wei Yan and De-Yin Wu supervised the research and revised the manuscript.
^#These authors are contributed equally to this work.

1. JOE2603031SI.pdf(5303KB)

摘要/Abstract

摘要：

对巯基苯胺不仅是表面增强拉曼光谱领域中广泛应用的探针分子，而且是界面反应的重要模型分子，具有独特的光氧化和电氧化途径，因此对巯基苯胺在不同的外加电场下被选择性激活。电化学氧化偶联过程中产物和中间产物的演变尚不清楚。采用循环伏安法、电化学表面增强拉曼光谱和原位电化学扫描隧道显微镜研究了对巯基苯胺在Au(111)表面的动态电化学氧化过程。结果表明，在酸性溶液中，对巯基苯胺在Au(111)表面形成不饱和吸附覆盖。当电位正移到氧化电位范围时，对巯基苯胺氧化产生的阳离子自由基与其分子交替排列。当偶联反应发生时，扫描隧道显微镜得到的图像中证实交替排列的吸附结构转变为条带结构。最后，Au(111)表面覆盖率降低，形成$\sqrt{3}\times 4\sqrt{6}$结构。氧化反应产物4′-巯基-N-苯醌二亚胺，在Au(111)上采用桥位和穴位混合吸附排列。通过测定对巯基苯胺在金表面电氧化过程中吸附结构的演变，从空间角度揭示了界面电化学氧化偶联反应的机理。这为进一步调控和设计芳香胺分子的界面反应奠定了基础。

关键词: 原位电化学扫描隧道显微镜, 对巯基苯胺, 4′-巯基-N-苯醌二亚胺, 电化学表面增强拉曼光谱

Abstract:

Para-aminothiophenol (PATP) is not only a widely-used probe molecule in the field of surface-enhanced Raman spectroscopy (SERS), but also an important model molecule for interfacial reactions, exhibiting distinct photo- and electro-oxidation pathways, so that PATP is selectively activated under different external fields. The evolution of products and intermediates during electrochemical oxidative coupling remains unknown. In this study, we have investigated the dynamic electrochemical oxidation process of PATP on the Au(111) surface using cyclic voltammetry, electrochemical (EC)-SERS, and in situ electrochemical scanning tunneling microscopy (EC-STM). The results showed that PATP forms an unsaturated adsorption coverage on Au(111) in an acidic solution. When the potential was positively shifted to the oxidation potential range, the cation radical generated by PATP oxidation alternated with PATP molecules in arrangement. Once the coupling reaction occurred, the adsorption structure of alternating arrangement was transformed into the stripe structure as observed in the STM images. Finally, the coverage on the Au(111) surface decreased and a $\sqrt{3}\times 4\sqrt{6}$. structure was formed. Accordingly, the oxidation reaction product 4′-mercapto-N-phenylquinone diimine (NPQD) would adopt the arrangement of mixed adsorption sites of bridge and hollow sites on Au(111). By determining the adsorption structure evolution of PATP during the electrooxidation process on the gold surface, the mechanism of interfacial electrochemical oxidation coupling reaction is revealed from a spatial perspective. This lays the foundation for further modulation and design of the interfacial reaction of aromatic amine molecules.

Key words: In situ electrochemical scanning tunneling microscopy, Para-aminothiophenol (PATP), 4'-mereapto-N-phenylquinone diimine, Electrochemical surface-enhanced Raman spectroscopy

马子为, 吴泰锐, 郑安妮, 陈来科, 肖远辉, 陈招斌, 郑轻娜, 周剑章, 颜佳伟, 吴德印. 对氨基硫酚在Au（111）上电化学氧化偶联过程中分子结构演变的原位扫描隧道显微镜可视化研究[J]. 电化学（中英文）, 2026, 32(7): 2603031.

Zi-Wei Ma, Tai-Rui Wu, An-Ni Zheng, Lai-Ke Chen, Yuan-Hui Xiao, Zhao-Bin Chen, Qing-Na Zheng, Jian-Zhang Zhou, Jia-Wei Yan, De-Yin Wu. In-Situ STM Visualization of Molecular Structural Evolution during Electrochemical Oxidation Coupling of Para-Aminothiophenol on Au(111)[J]. Journal of Electrochemistry, 2026, 32(7): 2603031.

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链接本文: https://electrochem.xmu.edu.cn/CN/10.61558/2993-074X.3614

https://electrochem.xmu.edu.cn/CN/Y2026/V32/I7/2603031

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对氨基硫酚在Au（111）上电化学氧化偶联过程中分子结构演变的原位扫描隧道显微镜可视化研究

In-Situ STM Visualization of Molecular Structural Evolution during Electrochemical Oxidation Coupling of Para-Aminothiophenol on Au(111)

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