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Thermally Induced Crosslinking of Poly(N-Propargyl Glycine)

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Secker,  Christian
Helmut Schlaad, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Brosnan,  Sarah M.
Helmut Schlaad, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Secker, C., Brosnan, S. M., Limberg, F. R. P., Braun, U., Trunk, M., Strauch, P., et al. (2015). Thermally Induced Crosslinking of Poly(N-Propargyl Glycine). Macromolecular Chemistry and Physics, 216(21), 2080-2085. doi:10.1002/macp.201500223.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0028-5434-C
Abstract
As polypeptoids become increasingly popular, they present a more soluble and processable alternative to natural and synthetic polypeptides; the breadth of their potential functionality slowly comes into focus. This report analyzes the ability of an alkyne-functionalized polypeptoid, poly(N-propargyl glycine), to crosslink upon heating. The crosslinking process is analyzed by thermal analysis (differential scanning calorimetry and thermogravimetric analysis), Fourier-transform infrared, electron paramagnetic resonance, and solid-state NMR spectroscopy. While a precise mechanism cannot be confidently assigned, it is clear that the reaction proceeds by a radical mechanism that exclusively involves the alkyne functionality, which, upon crosslinking, yields alkene and aromatic products.