3 years ago

H-Bonding Organocatalysts for the Living, Solvent-Free Ring-Opening Polymerization of Lactones: Toward an All-Lactones, All-Conditions Approach

H-Bonding Organocatalysts for the Living, Solvent-Free Ring-Opening Polymerization of Lactones: Toward an All-Lactones, All-Conditions Approach
Terra Marie M. Jouaneh, Kurt V. Fastnacht, Matthew K. Kiesewetter, Danielle N. Coderre, Nayanthara U. Dharmaratne, Jinal U. Pothupitiya
The developing urea class of H-bond donors facilitates the solvent-free ROP of lactones at ambient and elevated temperatures, displaying enhanced rates and control versus other known organocatalysts for ROP under solvent-free conditions. The ROPs retain the characteristics of living polymerizations despite solidifying prior to full conversion, and copolymers can be accessed in a variety of architectures. One-pot block copolymerizations of lactide and valerolactone, which had previously been inaccessible in solution phase organocatalytic ROP, can be achieved under these reaction conditions, and one-pot triblock copolymers are also synthesized. For the ROP of lactide, however, thioureas remain the more effective H-bond donating class. For all (thio)urea catalysts under solvent-free conditions and in solution, the more active catalysts are generally more controlled. A rationale for these observations is proposed. The triclocarban (TCC) plus base systems are particularly attractive in the context of solvent-free ROP due to their commercial availability which could facilitate the adoption of these catalysts.

Publisher URL: http://dx.doi.org/10.1021/acs.macromol.7b01991

DOI: 10.1021/acs.macromol.7b01991

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