Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 8, Pages 2755-2761Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b12888
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Funding
- Center for Sustainable Polymers, an NSF Center for Chemical Innovation [CHE-1413862]
- NSF through IGERT program [DGE-0903653]
- NSF [DMR-1120296]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1413862] Funding Source: National Science Foundation
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The synthesis of well-defined and functionalizable aliphatic polyesters remains a key challenge in the advancement of emerging drug delivery and self-assembly technologies. Herein, we investigate the factors that influence the rates of undesirable transesterification and epimerization side reactions at high conversion in the copolymerization of tricyclic anhydrides with excess propylene oxide using aluminum salen catalysts. The structure of the tricyclic anhydride, the molar ratio of the aluminum catalyst to the nucleophilic cocatalyst, and the Lewis acidity of the aluminum catalyst all influence the rates of these side reactions. Optimal catalytic activity and selectivity against these side reactions requires a careful balance of all these factors. Effective suppression of undesirable transesterification and epimerization was achieved even with sterically unhindered monomers using a fluorinated aluminum salph complex with a substoichiometric amount of a nucleophilic cocatalyst. This process can be used to synthesize well-defined block copolymers via a sequential addition strategy.
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