School of Chemistry, The University of New South Wales, Sydney NSW 2052, Australia.
Langmuir. 2011 Jun 7;27(11):6940-9. doi: 10.1021/la2013733. Epub 2011 May 10.
We demonstrate a simple method for coupling alkynes to alkynes. The method involves tandem azide-alkyne cycloaddition 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.
我们展示了一种将炔烃偶联到炔烃的简单方法。该方法涉及到叠氮-炔环加成反应（“点击”化学），用于将 1-炔烃物种在一锅法程序中固定到炔烃修饰的表面上。在所呈现的情况下，这些反应发生在未氧化的 Si(100)表面上，尽管该方法通常用于将炔烃偶联到炔烃上。该方法在制备电性能良好的功能化表面中的适用性通过将炔烃标记的二茂铁物种偶联到炔烃终止的 Si(100)表面上得到证明。该方法在生物技术中的应用通过用商业上可获得的炔烃标记的寡核苷酸对乙酰基表面进行衍生化来构建 DNA 传感界面得到证明。循环伏安法、电化学阻抗谱、X 射线光电子能谱和 X 射线反射率法用于表征偶联反应和最终修饰表面的性能。这些数据表明，这种合成方案在硅半导体表面上提供了化学定义明确、电性能良好且稳定的（生物）功能化单层。
