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Thermally Induced Crosslinking of Poly(N-Propargyl Glycine)
- 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.
| Author details: | Christian Secker, Sarah M. Brosnan, Felix Rolf Paul Limberg, Ulrike Braun, Matthias Trunk, Peter StrauchGND, Helmut SchlaadORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1002/macp.201500223 |
| ISSN: | 1022-1352 |
| ISSN: | 1521-3935 |
| Title of parent work (English): | Macromolecular chemistry and physics |
| Publisher: | Wiley-VCH |
| Place of publishing: | Weinheim |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2015 |
| Publication year: | 2015 |
| Release date: | 2017/03/27 |
| Tag: | Fourier-transform infrared; metal-free crosslinking; polypeptoid; propargyl; solid-state NMR |
| Volume: | 216 |
| Issue: | 21 |
| Number of pages: | 6 |
| First page: | 2080 |
| Last Page: | 2085 |
| Funding institution: | Max Planck Society; University of Potsdam; National Science Foundation Postdoctoral Research Fellowship in Biology [DBI-1308104] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
