Generation of surface-confined catechol terminated SAMs via electrochemically triggered Michael addition: characterization, electrochemistry and complex with Ni(II) and Cu(II) cations

作者：Tian, Yuan; Ye, Siqiu; Ran, Qin; Xian, Yuezhong^*; Xu, Jingjing; Peng, Ru; Jin, Litong

来源：Physical Chemistry Chemical Physics, 2010, 12(40): 13287-13295.

DOI：10.1039/c001205j

In this paper, catechol, 1,4-dihydroxybenzene and dopamine are investigated as precursors of electrophiles for Michael addition reaction with the self-assembled monolayer (SAM) of 4-thiouracil (4-TU) via electrochemical triggering. All compounds can undergo Michael addition reaction with 4-TU; however, only catechol can react with 4-TU with high efficiency. The catechol-terminated SAMs, via electrochemically triggered Michael addition reaction, exhibit reversible redox response. In addition, we find that catechol-terminated SAMs can complex with Ni(2 ) and Cu(2 ) with different electrochemical behaviors. Moreover, the mechanism of complexation of Ni(2 ) and Cu(2 ) with catechol-terminated SAMs is also demonstrated with electrochemical and spectrometric methods. Based on the different electrochemical behaviors of Cu(2 ) and Ni(2 ) complex, the catechol-terminated SAMs provide a potential platform for metal ions recognition.

• 出版日期2010
• 单位华东师范大学