Click chemistry is used to functionalize simple lipophilic and water-soluble molecules, a complex PEGylated phospholipid (DSPE-PEG2000), and two benzylic substrates with the 2-(hydroxyimino)aldehyde (HIA) group. To this end, two terminal alkynes bearing the HIA moiety were synthesized and coupled to different azides through copper(I)-catalyzed azide alkyne cycloaddition (CuAAC).
In the context of our research on stimuli-responsive polymers bearing the 2-(hydroxyimino)aldehyde (HIA) 2 group, we explore the photochemical behavior and physico-chemical properties of a number of HIAs. Interpretation of experimental data is supported by quantum mechanical calculations. HIAs are expected to undergo photoisomerization, chelate metal ions, yield hydrogen-bonded dimers or oligomers, exhibit relatively low pKas, and form >C=NO• radicals through OH hydrogen abstraction or oxidation of the oximate ion.
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