Web Release Date: February 6,
Ozonolysis-Based Route to the In Situ Formation of Aldehyde-Bearing Self-Assembled Monolayer Surfaces
and
Department of Chemistry and Center for Nanomaterials of the Institute for Nanotechnology, Bar Ilan University, Ramat Gan, Israel, and Department of Chemistry, University of California and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California 94720
Received October 8, 2007
In Final Form: December 3, 2007
Abstract:
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.
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