An alkene–azide 1,3‐dipolar cycloaddition between trans‐cyclooctene (TCO) and an azide‐capped hydrogel that promotes rapid gel dissolution is reported. Using an ultrashort aryl azide‐capped peptide hydrogel (PhePhe), we have demonstrated proof‐of‐concept where upon reaction with TCO, the hydrogel undergoes a gel–sol transition via 1,2,3‐triazoline degradation and 1,6‐self‐immolation of the generated aniline. The potential application of this as a general trigger in sustained drug delivery is demonstrated through release of encapsulated cargo (doxorubicin). Administration of TCO resulted in 87 % of the cargo being released in 10 h, compared to 13–14 % in the control gels. This is the first example of a potential bioorthogonal‐triggered hydrogel dissolution using a traditional click‐type reaction. This type of stimulus could be extended to other aryl azide‐capped hydrogels.
The wet and soft nature of hydrogels makes them useful as a mimic for biological tissues, and in uses such as actuators and drug delivery vehicles. For many applications the mechanical performance of the gel is critical, but gels are notoriously weak and prone to fracture. Free radical polymerization is a very powerful technique allowing for fine spatial and temporal control of polymerization, but also allows for the use of a wide range of monomers and mixtures. In this work, it is demonstrated that extremely tough and extensible hydrogels can be readily produced through simple radical polymerization of acrylamide or acrylic acid with a poly(ethylene oxide) macrocross-linker. These gels, with a water content of 85%, are extremely elastic with an extension much more than 15 000% at 9 MPa true stress. They can be compressed over 98% at a stress of 17 MPa. They are notch-insensitive, and the usual trouser tear test does not work because the tear simply does not propagate. This highly extensible nature seems to be related to very long chain lengths between cross-links and efficient incorporation of chains into the network.
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