Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate

Xiaoran Hu, Tian Zeng, Corey C. Husic, Maxwell J. Robb

Research output: Contribution to journalArticlepeer-review

73 Scopus citations

Abstract

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 for molecular release via a mechanically triggered cascade reaction. Mechanochemical activation of a furan-maleimide Diels-Alder adduct reveals a latent furfuryl carbonate that subsequently decomposes under mild conditions to release a covalently bound cargo molecule. The computationally guided design of a reactive secondary furfuryl carbonate enables the decomposition and release to proceed quickly at room temperature after unmasking via mechanical force. This general strategy is demonstrated using ultrasound-induced mechanical activation to release a fluorogenic coumarin payload from a polymer incorporating a chain-centered mechanophore.

Original languageEnglish (US)
Pages (from-to)15018-15023
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number38
DOIs
StatePublished - Sep 25 2019
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate'. Together they form a unique fingerprint.

Cite this