Tandem "click" reactions at acetylene-terminated Si(100) monolayers
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...
| Main Authors: | , , , |
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| Format: | Journal Article |
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American Chemical Society
2011
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| Online Access: | http://hdl.handle.net/20.500.11937/32087 |
| _version_ | 1848753564483059712 |
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| author | Ciampi, Simone James, M. Michaels, P. Gooding, J. |
| author_facet | Ciampi, Simone James, M. Michaels, P. Gooding, J. |
| author_sort | Ciampi, Simone |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | 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. © 2011 American Chemical Society. |
| first_indexed | 2025-11-14T08:26:31Z |
| format | Journal Article |
| id | curtin-20.500.11937-32087 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:26:31Z |
| publishDate | 2011 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-320872017-09-13T15:17:10Z Tandem "click" reactions at acetylene-terminated Si(100) monolayers Ciampi, Simone James, M. Michaels, P. Gooding, J. 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. © 2011 American Chemical Society. 2011 Journal Article http://hdl.handle.net/20.500.11937/32087 10.1021/la2013733 American Chemical Society restricted |
| spellingShingle | Ciampi, Simone James, M. Michaels, P. Gooding, J. Tandem "click" reactions at acetylene-terminated Si(100) monolayers |
| title | Tandem "click" reactions at acetylene-terminated Si(100) monolayers |
| title_full | Tandem "click" reactions at acetylene-terminated Si(100) monolayers |
| title_fullStr | Tandem "click" reactions at acetylene-terminated Si(100) monolayers |
| title_full_unstemmed | Tandem "click" reactions at acetylene-terminated Si(100) monolayers |
| title_short | Tandem "click" reactions at acetylene-terminated Si(100) monolayers |
| title_sort | tandem "click" reactions at acetylene-terminated si(100) monolayers |
| url | http://hdl.handle.net/20.500.11937/32087 |