Incorporation of a self-immolative spacer enables mechanically triggered dual payload release

Polymers that release functional small molecules in response to mechanical force are promising materials for a variety of applications including drug delivery, catalysis, and sensing. While many different mechanophores have been developed that enable the triggered release of a variety of small molecule payloads, most mechanophores are limited to one specific payload molecule. Here, we leverage the unique fragmentation of a 5-aryloxy-substituted 2-furylcarbinol derivative to design a novel mechanophore capable of the mechanically triggered release of two distinct cargo molecules. Critical to the mechanophore design is the incorporation of a self-immolative spacer to facilitate the release of a second payload. By varying the relative positions of each cargo molecule conjugated to the mechanophore, dual payload release occurs either concurrently or sequentially, demonstrating the ability to fine-tune the release profiles. Enabled by the unique fragmentation of a 5-aryloxy-substituted 2-furylcarbinol derivative, a self-immolative linker endows a mechanophore for achieving the mechanically triggered release of two distinct cargo molecules with tunable kinetic profiles.