4.6 Article

DNAzyme-Catalyzed Click Chemistry for Facilitated Immobilization of Redox Functionalities on Self-Assembled Monolayers

Journal

JOURNAL OF PHYSICAL CHEMISTRY C
Volume 124, Issue 35, Pages 19083-19090

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jpcc.0c05150

Keywords

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Funding

  1. Natural Science and Engineering Research Council (NSERC) of Canada
  2. National Natural Science Foundation of China [21974074]
  3. China Scholarship Council [201808330128]
  4. Shanxi University

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Cu( I)- catalyzed azide- alkyne cycloaddition (CuAAC), the representative reaction of modern click chemistry, has been broadly employed in organic synthesis, bio-labeling, and surface functionalization. Nevertheless, it has limitations such as posing a dilemma of either using high concentrations of Cu(I) catalyst or suffering from slow kinetics. Herein, we demonstrate that a newly selected DNAzyme (CLICK-17; a 79-nucleotide, catalytic DNA single strand) can rapidly catalyze CuAAC to tether redox functionalities onto an electrode surface using low concentrations of either Cu(I) or Cu (II). Particularly, the CLICK-17 DNAzyme, at mu M concentrations, facilitated the covalent immobilization of ethynylferrocene (Fc-C CH) onto 1-azido-11-undecanethiolate self-assembled monolayers on gold (N3C11S-Au SAMs); as low as 50 mu M Cu(I) together with 4 mu M DNAzyme was able to complete the coupling reaction within 30 min and the pseudo first-order reaction rate constant is 7 times higher than that using the Cu(I) catalyst alone. It was also remarkable that the CLICK-17 DNAzyme is functional with Cu(II) in the absence of an explicit reductant for the catalyzed surface immobilization of Fc-C CH on N3C11S-Au SAMs.

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