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Issue 2, 2017
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Self-reporting dynamic covalent polycarbonate networks

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Abstract

Here, we report the first-time development of polycarbonate networks with self-reporting thermoreversible bonding/debonding on demand properties. The reversible linkages within the network are based on a Hetero–Diels–Alder (HDA) moiety, which is able to undergo cleavage and rebonding as a function of temperature within minutes. As HDA pair a phosphoryl dithioester and a cyclopentadiene moiety are employed as bonding and debonding take place in the temperature range between 25–120 °C. The degradation and rebonding can be readily traced by visible inspection due to the self-reporting nature of the HDA moiety. In order to prove the reversibility, linear polycarbonates (Mw = 4.200–20.000 g mol−1) including the reversible linkage in each repeating unit were generated and carefully analyzed using size exclusion chromatography (SEC), UV/Vis analysis and high temperature 1H NMR spectroscopy. Subsequently, polycarbonate networks bearing HDA units – allowing the networks to be fully degraded into small molecules – were synthesized, debonded and bonded several times in the temperature range between 25 and 120 °C within minutes. The present study thus introduces fully degradable polycarbonate networks based on a facile chemical concept as a viable alternative to networks based on C–C bond formation that disallow a complete degradation.

Graphical abstract: Self-reporting dynamic covalent polycarbonate networks

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Publication details

The article was received on 19 Oct 2016, accepted on 14 Nov 2016 and first published on 15 Nov 2016


Article type: Paper
DOI: 10.1039/C6PY01840H
Citation: Polym. Chem., 2017,8, 414-420
  • Open access: Creative Commons BY license
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    Self-reporting dynamic covalent polycarbonate networks

    A. M. Schenzel, N. Moszner and C. Barner-Kowollik, Polym. Chem., 2017, 8, 414
    DOI: 10.1039/C6PY01840H

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