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Synthesis and characterization of light-degradable bromocoumarin functionalized polycarbonates

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Abstract

Biocompatible polymeric materials that can degrade in response to external irradiation with high spatial and temporal control show enormous potential in the field of biomedical applications. Herein, two six-membered cyclic carbonate monomers with a light-cleavable bromocoumarin functional pendent moiety attached via a carbamate linkage were prepared from 2-amino-1,3-propanediol (serinol) and 2-(aminomethyl)-2-methylpropane-1,3-diol, respectively. A series of light-degradable polycarbonates were synthesized by organo-catalyzed ring opening polymerization (ROP) of both monomers, and meanwhile their polymerization kinetics were investigated. Upon light-induced deprotection, both types of polycarbonates degraded rapidly into low molecular-weight compounds. The results of size exclusion chromatography (SEC), nuclear magnetic resonance (NMR) spectroscopy and ultraviolet/visible (UV/VIS) spectroscopy confirmed the polymer structures and the light-induced degradation behavior. The photo-cleavage rates of bromocoumarin pendent groups and the degradation rates of the polymers were strongly dependent on polymer structures and used solvents.

Graphical abstract: Synthesis and characterization of light-degradable bromocoumarin functionalized polycarbonates

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Publication details

The article was received on 18 Sep 2019, accepted on 19 Nov 2019 and first published on 26 Nov 2019


Article type: Paper
DOI: 10.1039/C9PY01405E
Polym. Chem., 2020, Advance Article

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    Synthesis and characterization of light-degradable bromocoumarin functionalized polycarbonates

    A. Müller, D. Jung, J. Sun and D. Kuckling, Polym. Chem., 2020, Advance Article , DOI: 10.1039/C9PY01405E

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