Disulfone Cross-Linkers for λ-Orthogonal Photoinduced Curing and Degradation of Polymeric Networks
We introduce a new concept for λ-orthogonal photocurable and degradable polymer networks based on disulfone cross-linkers. The methacrylate-based monomer mixture can be cured via irradiation with visible light (400–520 nm) due to a germanium-based initiator in 10 min. Subsequently, disassembly can be induced via the UV light (350–400 nm) triggered decomposition of a photogenerated amine (PGA) that cleaves the disulfone cross-links of the network completely via a substitution reaction. For the disulfone-based cross-linking, a new dimethacrylate monomer containing the disulfone moiety is synthesized. The cleavage of the S–S bond via a nucleophilic substitution is evidenced using 5 equiv of diethylamine as a nucleophile. In order to achieve an in situ degradation, a UV-degradable PGA is prepared, and its degradation upon UV irradiation as well as its stability under visible light are demonstrated. 1 H NMR spectroscopy in solution revealed a complete degradation of the disulfone in the presence of 5 equiv of the PGA. Finally, a swollen network was prepared and successfully degraded upon UV irradiation within 4 h. Graphic Abstract ACS Electronic Supporting Info
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