4.6 Article

Tandem Click Reactions at Acetylene-Terminated Si(100) Monolayers

Journal

LANGMUIR
Volume 27, Issue 11, Pages 6940-6949

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/la2013733

Keywords

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Funding

  1. Australian Research Council [DP1094564]
  2. Australian Research Council [DP1094564] Funding Source: Australian Research Council

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We demonstrate a simple method for coupling alkynes to alkynes. The method involves tandem azide-alkyne cyclo addition reactions (click chemistry) for the immobilization of 1-alkyne species onto an alkyne modified surface in a one-pot procedure. In the case presented, these reactions take place on a nonoxidized Si(100) surface although the approach is general for linking alkynes to alkynes. The applicability of the method in the preparation of electrically well-behaved functionalized surfaces is demonstrated by coupling an alkyne-tagged ferrocene species onto alkyne-terminated Si(100) surfaces. The utility of the approach in biotechnology is shown by constructing a DNA sensing interface by derivatization of the acetylenyl surface with commercially available alkyne-tagged oligonucleotides. Cyclic voltametry, electrochemical impedance spectroscopy, X-ray photoelectron spectroscopy, and X-ray reflectometry are used to characterize the coupling reactions and performance of the final modified surfaces. These data show that this synthetic protocol gives chemically well-defined, electronically well-behaved, and robust (bio)functionalized monolayers on silicon semiconducting surfaces.

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