ArticleACS central science2021
Mechanically Triggered Release of Functionally Diverse Molecular Payloads from Masked 2-Furylcarbinol Derivatives.
Article in ACS central science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Tailored Nanogel Network Topology Enables Clinical Ultrasound-Induced Mechanochemical Activation for In Vivo Therapy.Angewandte Chemie (International ed. in English) · 2026Article
- Mechanical Taming of Hardy-Cope Rearrangements.ACS central science · 2026Article
- Modeling Targeted Mechanochemistry in Polymeric Solids.Chemical reviews · 2026Review
- Coordination chemistry-enabled drug delivery systems: metal-ligand platforms for controlled release and targeted therapeutics.Journal of nanobiotechnology · 2026Review
- A Noncovalent Click-to-Release Strategy to Control Bond Cleavage and Prodrug Activation.Angewandte Chemie (International ed. in English) · 2026Article
- Live-Cell RNA Imaging via Clickable TriPPPro Nucleotide Reporters.Angewandte Chemie (International ed. in English) · 2026Article
- Polymer microbubbles as universal platform to accelerate polymer mechanochemistry.Nature communications · 2025Article
- Advancing the Mechanosensitivity of Atropisomeric Diarylethene Mechanophores through a Lever-Arm Effect.Journal of the American Chemical Society · 2025Article
- Article
- Ultrasound-Controlled Prodrug Activation: Emerging Strategies in Polymer Mechanochemistry and Sonodynamic Therapy.ACS applied bio materials · 2024Review
- Sonopharmacology: Regulation of drug activity through ultrasound.Journal of pharmaceutical analysis · 2024Article
- Mechanically Triggered Bright Chemiluminescence from Polymers by Exploiting a Synergy between Masked 2-Furylcarbinol Mechanophores and 1,2-Dioxetane Chemiluminophores.Journal of the American Chemical Society · 2024Article
- A novel bioresponsive self-immolative spacer based on aza-quinone methide reactivity for the controlled release of thiols, phenols, amines, sulfonamides or amides.Chemical science · 2024Article
- Incorporation of a self-immolative spacer enables mechanically triggered dual payload release.Chemical science · 2024Article
- Multimechanophore Polymers for Mechanically Triggered Small Molecule Release with Ultrahigh Payload Capacity.Journal of the American Chemical Society · 2024Article
- Naphthopyran molecular switches and their emergent mechanochemical reactivity.Chemical science · 2023Review
- Furan Release via Force-Promoted Retro-[4+2][3+2] Cycloaddition.Journal of the American Chemical Society · 2023Article
- Remote control of mechanochemical reactions under physiological conditions using biocompatible focused ultrasound.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Preferential Mechanochemical Activation of Short Chains in Bidisperse Triblock Elastomers.ACS macro letters · 2023Article
- Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers.Journal of the American Chemical Society · 2023Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Polymers that release functional small molecules in response to mechanical force are appealing targets for drug delivery, sensing, catalysis, and many other applications. Mechanically sensitive molecules called mechanophores are uniquely suited to enable molecular release with excellent selectivity and control, but mechanophore designs capable of releasing cargo with diverse chemical functionality are limited. Here, we describe a general and highly modular mechanophore platform based on masked 2-furylcarbinol derivatives that spontaneously decompose under mild conditions upon liberation via a mechanically triggered reaction, resulting in the release of a covalently installed molecular payload. We identify key structure-property relationships for the reactivity of 2-furylcarbinol derivatives that enable the mechanically triggered release of functionally diverse molecular cargo with release kinetics being tunable over several orders of magnitude. In particular, the incorporation of an electron-donating phenoxy group on the furan ring in combination with an α-methyl substituent dramatically lowers the activation barrier for fragmentation, providing a highly active substrate for molecular release. Moreover, we find that phenoxy substitution enhances the thermal stability of the mechanophore without adversely affecting its mechanochemical reactivity. The generality and efficacy of this molecular design platform are demonstrated using ultrasound-induced mechanical force to trigger the efficient release of a broad scope of cargo molecules, including those bearing alcohol, phenol, alkylamine, arylamine, carboxylic acid, and sulfonic acid functional groups.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.