The incorporation of reactive functionalities onto polymer backbones has attracted significant attention and has been extensively studied by many researchers to create highly-functionalized polymeric materials.  This work involves the development of a facile synthetic method for aldehyde-functional polycarbonates, which could be utilized as reactive platforms to construct a variety of functional dynamic and/or static polymer materials under mild reaction conditions.  Versatile allyl-functional polycarbonates were synthesized by ring-opening polymerization of a functionalized cyclic carbonate monomer using 1,8-diazabicyclo [5.4.0]undec-7-ene as an organocatalyst.  Pendant alkene groups were efficiently converted into aldehydes by ozonolysis and reductive work-up.  We demonstrated that two model aminooxy compounds were efficiently installed onto the well-defined polycarbonate backbones by reactions with aldehydes forming oxime linkages.  In addition, alkenes and aldehydes were readily introduced as orthogonal functional groups, by partial ozonolysis and the resulting statistical copolymer was functionalized by stepwise aldehyde-aminooxy and thiol-ene �click� reactions in an orthogonal manner.  This efficient approach for the preparation and modification of versatile degradable polymer platforms will be useful to a wide range of research areas due to their capability to form various conjugates via combinations of oxime, hydrazone, and/or Schiff base linkages with aldehydes and also thioether or other linkages to the alkenes.

Aldehyde-functional polycarbonates as reactive platforms

248th National Meeting (2014)

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