ma4001258_si_001.pdf (320.95 kB)
Accessing New Materials through Polymerization and Modification of a Polycarbonate with a Pendant Activated Ester
journal contribution
posted on 2013-02-26, 00:00 authored by Amanda C. Engler, Julian M. W. Chan, Daniel
J. Coady, Jeannette M. O’Brien, Haritz Sardon, Alshakim Nelson, Daniel
P. Sanders, Yi Yan Yang, James L. HedrickFunctionalized polycarbonates were synthesized by organocatalytic
ring-opening polymerization (ROP) of a cyclic monomer with a pendant
activated ester (MTC-OC6F5) followed by a postpolymerization
modification with both small molecules and macromolecules. Controlled
ROP to form homopolymers and diblock copolymers was realized using
catalytic quantities of triflic acid. For the homopolymers, a linear
relationship between [M]0/[I]0 and molecular
weight (by GPC) demonstrated the living nature of the polymerization.
Poly(MTC-OC6F5) was functionalized under mild
reaction conditions with a variety of amines to obtain polymers with
pendant primary, secondary, and tertiary amides. Graft polymers with
a high grafting density of over 87% were synthesized using amine-terminated
poly(ethylene glycol) of two different molecular weights (2 and 5
kDa). The preparation of poly(MTC-OC6F5) provides
a means of accessing a wide range of functional polycarbonates with
minimal synthetic steps. This new methodology for the formation of
functionalized polycarbonates provides a simple and versatile platform
for the synthesis of new and innovative materials.