Journal
SURFACE SCIENCE
Volume 648, Issue -, Pages 284-290Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.susc.2015.10.004
Keywords
Acyloxysilane; Paired bifunctional groups; Bifunctional surface; Surface modification; Cooperative effect
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Funding
- Office of Basic Energy Sciences, US Department of Energy [DE-FG02-01ER15184]
- NSF [CHE-1048773]
- Int. Institute of Nanotechnology
- NUANCE facilities at Northwestern University
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Grafting of pairs of functional groups onto a silica surface was demonstrated by tethering both terminals of an organochlorosilane precursor molecule, Cl-2(CH3)Si(CH2)(4)(CO)(OSi(i-Pr)(2))(CH2)(2)Si(CH3)Cl-2, that possess a cleavable silyl ester bond, onto a silica surface. Hydrolytic cleavage of the silyl ester bond of the grafted molecule resulted in the generation of organized pairs of carboxylic acid and organosilanol groups. This organosilanol moiety was easily transformed into other functional groups through condensation reactions to form, together with the neighboring acid group, pairs such as carboxylic acid/secondary amine, carboxylic acid/pyridine, and carboxylic acid/phosphine. In the case of carboxylic acid/amine pairing, there was evidence of the formation of amide. A sample grafted with amine-carboxylic acid pairs was three times more active (per free amine) than a sample without such pairs for the nitroaldol condensation of 4-nitrobenzaldehyde and nitromethane. (C) 2015 Elsevier B.V. All rights reserved.
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