Issue 28, 2021

Photo-liberated amines for N-carboxyanhydride (PLANCA) ring-opening polymerization

Abstract

The polymerization of N-carboxyanhydrides (NCAs) affords access to a vast array of synthetic polypeptides with tunable molecular weights, functionalities, and architectures. The use of light to achieve spatiotemporal control over these polymerizations could expand their applicability to a variety of areas, including 3D printing and photolithography. In this report we utilized 2-(2-nitrophenyl)propyloxycarbonyl (NPPOC) as a photoprotecting group to cage a primary amine initiator that is activated upon UV irradiation. NPPOC photocages underwent quantitative deprotection and afforded better polymerization control compared to previously reported photocaged amines for NCA polymerizations. Furthermore, the addition of a small equivalence of base enhanced the control and resulted in polymers with lower dispersities. Overall, this method advances photo-controlled polypeptide synthesis by demonstrating high chain-end fidelity, efficient chain extension, and the ability to synthesize block copolymers.

Graphical abstract: Photo-liberated amines for N-carboxyanhydride (PLANCA) ring-opening polymerization

Supplementary files

Article information

Article type
Paper
Submitted
09 Jun 2021
Accepted
16 Jun 2021
First published
09 Jul 2021

Polym. Chem., 2021,12, 4104-4110

Author version available

Photo-liberated amines for N-carboxyanhydride (PLANCA) ring-opening polymerization

S. L. Goodrich, M. R. Hill, R. A. Olson and B. S. Sumerlin, Polym. Chem., 2021, 12, 4104 DOI: 10.1039/D1PY00781E

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