| AVS 59th Annual International Symposium and Exhibition | |
| Thin Film | Thursday Sessions |
| Session TF+EM+SS-ThA |
| Session: | Applications of Self-Assembled Monolayers and Layer-by-Layer Assemblies |
| Presenter: | N.S. Bhairamadgi, Wageningen University, Netherlands |
| Authors: | N.S. Bhairamadgi, Wageningen University, Netherlands H. Zuilhof, Wageningen University, Netherlands |
| Correspondent: | Click to Email |
Click chemistry reactions have opened new horizons in the field of surface chemistry, as these reactions are ease to perform on surfaces. A nice example is the addition of thiol moieties onto C=C bonds, which have been shown to be highly efficient, orthogonal to many other reactions, highly selective, etc. Recently we and others have shown that thiol-ene click reactions can be used efficiently for the modification of semiconductor surfaces and nanoparticles with a wide range of materials. In the current presentation we show an improved procedure involving C≡C bonds, i.e. thiol-yne click reactions.
We modified oxide-free Si(111) surfaces with alkene-terminated and alkyne-terminated monolayers, and these surfaces were further modified with various thiols such as thioglycolic acid, thioacetic acid, thioglycerol, thio-β-D-glucose tetraacetate lactose and 9-flurenylmethoxy-carbonyl cysteine by using thiol-ene and thiol-yne click reactions. Upon detailed surface analysis it was found that after some optimization the thiol-yne click reaction yielded 20 – 80 % more surface coverage compared to thiol-ene click reactions. Thus surface modification with thiol-yne click reactions promise to be the next step in surface-bound thiol click chemistry.
References:
1. Campos, M. A. C.; Paulusse, J. M. J.; Zuilhof, H., Functional monolayers on oxide- free silicon surfaces via thiol-ene click chemistry. Chem. Commun. 2010, 46 (30), 5512-5514.
2. Lowe, A. B.; Hoyle, C. E.; Bowman, C. N., Thiol-yne click chemistry: A powerful and versatile methodology for materials synthesis. J. Mater. Chem. 2010, 20 (23), 4745- 4750.
3. Ruizendaal, L.; Pujari, S. P.; Gevaerts, V.; Paulusse, J. M. J.; Zuilhof, H., Biofunctional Silicon Nanoparticles by Means of Thiol-Ene Click Chemistry. Chem. Asian J. 2011, 6 (10), 2776-2786.
4. Wendeln, C.; Ravoo, B. J., Surface Patterning by Microcontact Chemistry. Langmuir 2012, 28 (13), 5527-5538.
5. Wendeln, C.; Rinnen, S.; Schulz, C.; Arlinghaus, H. F.; Ravoo, B. J., Photochemical Microcontact Printing by Thiol−Ene and Thiol−Yne Click Chemistry. Langmuir 2010, 26 (20), 15966-15971.