Post-Polymerization Modification of Branched Polyglycidol with N-Hydroxy Phthalimide to Give Ratio-Controlled Amino-Oxy Functionalized Species

Ratio-controlled amino-oxy functionalized, branched polyglycidols are prepared by a post-polymerizaton modification using and optimizing the Mitsunobu reaction for this purpose. The hydroxyl side-groups are functionalized with N-hydroxy phthalimide and the hydrazinolysis of this group furnishes a new class of branched polyglycidols with pendant amino-oxy groups. Reproducible functionalization degrees of 17, 33, 43, and 63% of the hydroxyl groups are obtained via the presented developed methodology. MTT assays demonstrate the biocompatibility of amino-oxy functionalized materials. With this, the prepared structural motifs are valuable precursors for the synthesis of biomaterials, bioconjugates and hydrogels in which orthogonal strategies are desired. (C) 2016 Wiley Periodicals, Inc.