Complex,degradable polyester materials via ketoxime ether‐based functionalization: Amphiphilic,multifunctional graft copolymers and their resulting solution‐state aggregates |
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Authors: | Rhiannon K Iha Brooke A van Horn Karen L Wooley |
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Institution: | 1. Department of Chemistry, Washington University in Saint Louis, Saint Louis, Missouri 63130‐4899;2. Department of Chemistry and Biochemistry, The College of Charleston, Charleston, South Carolina 29424;3. Department of Chemistry, Texas A&M University, College Station, Texas 77842 |
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Abstract: | Degradable, amphiphilic graft copolymers of poly(ε‐caprolactone)‐graft‐poly(ethylene oxide), PCL‐g‐PEO, were synthesized via a grafting onto strategy taking advantage of the ketones presented along the backbone of the statistical copolymer poly(ε‐caprolactone)‐co‐(2‐oxepane‐1,5‐dione), (PCL‐co‐OPD). Through the formation of stable ketoxime ether linkages, 3 kDa PEO grafts and p‐methoxybenzyl side chains were incorporated onto the polyester backbone with a high degree of fidelity and efficiency, as verified by NMR spectroscopies and GPC analysis (90% grafting efficiency in some cases). The resulting block graft copolymers displayed significant thermal differences, specifically a depression in the observed melting transition temperature, Tm, in comparison with the parent PCL and PEO polymers. These amphiphilic block graft copolymers undergo self‐assembly in aqueous solution with the P(CL‐co‐OPD‐co‐(OPD‐g‐PEO)) polymer forming spherical micelles and a P(CL‐co‐OPD‐co‐(OPD‐g‐PEO)‐co‐(OPD‐g‐pMeOBn)) forming cylindrical or rod‐like micelles, as observed by transmission electron microscopy and atomic force microscopy. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3553–3563, 2010 |
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Keywords: | aminooxy amphiphiles amphiphilic copolymer block copolymers block graft copolymer graft copolymers heterograft copolymer ketoxime ether poly(ε ‐caprolactone) poly(ethylene oxide) |
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