Since its discovery in 1969, the coupling of epoxides and CO2 has provided an attractive pathway for polycarbonate production. With the recent development in better catalytic systems, a lot of epoxides have been successfully copolymerized with CO2. Nevertheless, the hydrophobic nature and lack of functionalities of these polycarbonates have limited their applications. In this work, we demonstrate an effective approach to prepare a variety of functional polycarbonates derived from CO2. 3,4-epoxy-tert-butyl-3-butenoate (1) is synthesized followed by copolymerization with CO2 to make polycarbonate. Steric effect of the coupling reaction will be addressed. Subsequently, the resulting polymer undergoes deprotection to give polymer 2 with a carboxylic acid as a pendant group. Upon amination or esterification, the COOH group is converted to different functionalities, such as amine, oligotheylene glycol, chloride, N-heterocycle, etc. The utilization of these functionalities to attach bioactive compounds will also be discussed. These emerging classes of CO2-based polycarbonates will provide a powerful platform for biomedical applications.

Carboxylic acid functionalized polycarbonates from CO2: A versatile platform for the synthesis of functional polycarbonates

251st National Meeting (2016)

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