Construction of Versatile and Functional Nanostructures Derived from CO2-based Polycarbonates

• Published in: Angewandte Chemie International Edition 2015-08, Vol.54 (35), p.10206-10210
• Main Authors: Wang, Yanyan, Fan, Jingwei, Darensbourg, Donald J.
• Format: Article
• Language: English
• Subjects: carbon dioxide; Chemical industry; epoxide; micelles; nanoparticles; polycarbonates
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201505076

The construction of amphiphilic polycarbonates through epoxides/CO2 coupling is a challenging aim to provide more diverse CO2‐based functional materials. In this report, we demonstrate the facile preparation of diverse and functional nanoparticles derived from a CO2‐based triblock polycarbonate system. By the judicious use of water as chain‐transfer reagent in the propylene oxide/CO2 polymerization, poly(propylene carbonate (PPC) diols are successfully produced and serve as macroinitiators in the subsequent allyl glycidyl ether/CO2 coupling reaction. The resulting ABA triblock polycarbonate can be further functionalized with various thiols by radical mediated thiol–ene click chemistry, followed by self‐assembly in deionized water to construct a versatile and functional nanostructure system. This class of amphiphilic polycarbonates could embody a powerful platform for biomedical applications. A two step, one‐pot synthesis of an amphiphilic triblock polycarbonate from CO2 and propylene oxide is described. The poly(propylene carbonate) diols produced in the first step serve as macroinitiators in the subsequent allyl glycidyl ether/CO2 coupling reaction leading to self‐assembled triblock PC nanoparticles following postmodification by thiol–ene click chemistry.