mixture was diluted with dichloromethane and washed with brine. The organic solvent was evaporated in
vacuo and the brown residue purified via column chromatography (ethyl acetate/light petroleum`, 1:1) to
yield the unreacted starting material e and traces of the coumarin d.
9.
Clayden, J.; Greeves, N.; Warren, S.; Wothers, P., Organic Chemistry. Oxford University Press:
Oxford, 2001.
10.
Chemical oxidation of the confined lactone 2 leads to the exposure of a conveniently presented
carboxylic acid functionality`, thus allowing further derivatization of the organic film.
11.
Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B., A Stepwise Huisgen
Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes.
Angew. Chem., Int. Ed. 2002, 41, (14), 2596-2599.
12.
Ciampi, S.; Böcking, T.; Kilian, K. A.; James, M.; Harper, J. B.; Gooding, J. J., Functionalization
of Acetylene-Terminated Monolayers on Si(100) Surfaces: A Click Chemistry Approach. Langmuir 2007,
23, (18), 9320-9329.
13.
Tornoe, C. W.; Christensen, C.; Meldal, M., Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by
Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org.
Chem. 2002, 67, (9), 3057-3064.
14.
of undecylenic acid with porous silicon. J. Electrochem. Soc. 2002, 149, (2), H59-H63.
15. Ciampi, S.; Le Saux, G.; Harper, J. B.; Gooding, J. J., Optimization of Click Chemistry of
Boukherroub, R.; Wojtyk, J. T. C.; Wayner, D. D. M.; Lockwood, D. J., Thermal hydrosilylation
Ferrocene Derivatives on Acetylene-Functionalized Silicon(100) Surfaces Electroanalysis 2008, 20, (14),
1513-1519.
16.
Ciampi, S.; Eggers, P. K.; Le Saux, G.; James, M.; Harper, J. B.; Gooding, J. J., Silicon (100)
Electrodes Resistant to Oxidation in Aqueous Solutions: An Unexpected Benefit of Surface Acetylene
Moieties. Langmuir 2009, 25, (4), 2530-2539.
17.
purified via column chromatography (ethyl acetate/light petroleum`, 1:2).
18. Kolb, H. C.; Sharpless, K. B., The growing impact of click chemistry on drug discovery. Drug
Discovery Today 2003, 8, (24), 1128-1137.
19. Meda, L.; Cerofolini, G. F., A decomposition procedure for the determination of copper oxidation
states in Cu-zeolites by XPS. Surf. Interface Anal. 2004, 36, (8), 756-759.
20. Meda, L.; Ranghino, G.; Moretti, G.; Cerofolini, G. F., XPS detection of some redox phenomena
in Cu-zeolites. Surf. Interface Anal. 2002, 33, (6), 516-521.
21. Janolino, V. G.; Swaisgood, H. E., Analysis and optimization of methods using water-soluble
The unreacted lactone 2 used in surface modification procedures was routinely recovered and
carbodiimide for immobilization of biochemicals to porous glass. Biotechnol. Bioeng. 1982, 24, (5),
1069-1080.
22.
in a separate report under preparation.
23. Stalder, A. F.; Melchior, T.; Müller, M.; Sage, D.; Blu, T.; Unser, M., Low-Bond Axisymmetric
Chemical reduction of the benzoquinone linker was also investigated. A detailed account is found
Drop Shape Analysis for Surface Tension and Contact Angle Measurements of Sessile Drops. Colloids
Surf., B 2010, 364, (1-3), 72-81.
24.
Webb, L. J.; Lewis, N. S., Comparison of the Electrical Properties and Chemical Stability of
Crystalline Silicon(111) Surfaces Alkylated Using Grignard Reagents or Olefins with Lewis Acid
Catalysts. J. Phys. Chem. B 2003, 107, (23), 5404-5412.
25.
Haber, J. A.; Lewis, N. S., Infrared and X-ray Photoelectron Spectroscopic Studies of the
Reactions of Hydrogen-Terminated Crystalline Si(111) and Si(100) Surfaces with Br2, I2, and
Ferrocenium in Alcohol Solvents. J. Phys. Chem. B 2002, 106, (14), 3639-3656.
26.
27.
XPS atomic sensitivities were 1.00 for C 1s`, 0.276 for Si 2p`, 2.93 for O 1s and 0.86 for N 1s.
Nelson, A., Co-refinement of multiple-contrast neutron/X-ray reflectivity data using MOTOFIT.
J. Appl. Cryst. 2006, 39, 273-276.
28. Press, W. H.; Flannery, B. P.; Teukolsky, S. A.; Vetterling, W. T., Numerical Recipes in C: The
Art of Scientific Computing. Cambridge Univeristy Press: Cambridge, 1988.
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