Generation of surface-confined catechol terminated SAMs via electrochemically triggered Michael addition: characterization, electrochemistry and complex with Ni(II) and Cu(II) cations.
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.
Tian
Yuan
Y
Department of Chemistry, East China Normal University, Shanghai 200062, China.
Ye
Siqiu
S
Ran
Qin
Q
Xian
Yuezhong
Y
Xu
Jingjing
J
Peng
Ru
R
Jin
Litong
L