ArticleAngewandte Chemie (International ed. in English)2022
Mechanoresponsive Carbamoyloximes for the Activation of Secondary Amines in Polymers.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- The mechanochemical activation of a pyrimidine dimer.Chemical science · 2026Article
- Precise Mechanochemical Scission of DNA Guided by Secondary Structures.Journal of the American Chemical Society · 2026Article
- Efficient, Functional Group-Tolerant, and Catalyst-Free Nitrile Formation from Aldehydes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Ultrasound-Controlled Prodrug Activation: Emerging Strategies in Polymer Mechanochemistry and Sonodynamic Therapy.ACS applied bio materials · 2024Review
- Coumarin Dimer Is an Effective Photomechanochemical AND Gate for Small-Molecule Release.Journal of the American Chemical Society · 2023Article
- Sonopharmacology: controlling pharmacotherapy and diagnosis by ultrasound-induced polymer mechanochemistry.Chemical science · 2022Review
- Mechanoresponsive Carbamoyloximes for the Activation of Secondary Amines in Polymers.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
2 authors.
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Abstract
Mechanophores are molecular moieties that are incorporated into polymers and respond to force with constitutional, configurational, or conformational bond rearrangements to enable functionality. Up to today, several chemically latent motifs have been activated by polymer mechanochemical methods, but the generation of secondary amines remains elusive. Here we report carbamoyloximes as mechanochemical protecting groups for secondary amines. We show that carbamoyloximes undergo force-induced homolytic bond scission at the N-O oxime bond in polymers thus producing the free amine, as the reaction proceeds via the carbamoyloxyl and aminyl radicals, analogously to its photochemical counterpart. Eventually, we apply the carbamoyloxime motif in a force-activated organocatalytic Knoevenagel reaction. We believe that this protecting strategy can be universally applied for many other secondary and primary amines in polymer materials.
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Registered trials
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