Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate

• DOI: 10.1021/jacs.9b08663
• Publication Date: 2019-09-13T12:22:19Z
• Authors: Xiaoran Hu; Tian Zeng; Corey C. Husic; Maxwell J. Robb
• Keywords: Maleimide; Furfuryl alcohol; Furan

Stimuli-responsive polymers that release small molecules under mechanical stress are appealing targets for applications ranging from drug delivery to sensing. Here, we describe a modular mechanophore design platform molecular via mechanically triggered cascade reaction. Mechanochemical activation of furan–maleimide Diels–Alder adduct reveals latent furfuryl carbonate subsequently decomposes mild conditions covalently bound cargo molecule. The computationally guided reactive secondary enables the decomposition and proceed quickly at room temperature after unmasking force. This general strategy is demonstrated using ultrasound-induced fluorogenic coumarin payload polymer incorporating chain-centered mechanophore.