Issue 2, 2017

Self-reporting dynamic covalent polycarbonate networks


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

Supplementary files

Article information

Article type
19 Oct 2016
14 Nov 2016
First published
15 Nov 2016
This article is Open Access
Creative Commons BY license

Polym. Chem., 2017,8, 414-420

Self-reporting dynamic covalent polycarbonate networks

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity