Ozonolysis-based route to the in situ formation of aldehyde-bearing self-assembled monolayer surfaces.
While ozonolysis of a terminal carbon-carbon double bond to produce aldehydes is a well-established synthetic strategy for conventional solution chemistry, exposure of vinyl-terminated self-assembled monolayers to ozone has been reported to yield carboxylic acids. By using a cold solution of ozone in methanol and then adding a reducing agent to this solution, acid formation is minimized and near-quantitative aldehyde formation is achieved. The aldehyde-bearing surface is characterized by its physical and chemical properties and by ATR-FTIR spectroscopy showing a characteristic aldehyde C-H peak at 2715 cm(-1) and carbonyl peak at 1729 cm(-1). The reactivity of the aldehyde-bearing surface is shown by its reaction with amines and amine derivatives to give surface-bound imines and by the reversible cycling between aldehyde and acetal. The acetal also provides a useful way to mask the aldehyde and store readily released aldehyde surface functionality for subsequent surface elaboration.
Razgon
Anna
A
Department of Chemistry and Center for Nanomaterials of the Institute for Nanotechnology, Bar Ilan University, Ramat Gan, Israel.
Bergman
Robert G
RG
Sukenik
Chaim N
CN
D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D006868:Hydrolysis; D008567:Membranes, Artificial; D010126:Ozone / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013499:Surface Properties
D000447:Aldehydes; D002264:Carboxylic Acids; D008567:Membranes, Artificial; D010126:Ozone; D012825:Silicon