ArticleChemical science2021
Structure-function relationships in aryl diazirines reveal optimal design features to maximize C-H insertion.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Universal charge-tag labelling of undetectable polymers for mass spectrometric characterization.Chemical science · 2026Article
- Assessment of Protein Conformation via Diazirine-Promoted Oxidation of Methionine and Tryptophan Residues.Analytical chemistry · 2026Article
- Inherent MS-cleavability of diazirine photo-cross-links enables residue-level structural analysis.Nature communications · 2026Article
- Electrostatic-confinement-induced regioselective C-H functionalization of polyolefins.Nature communications · 2026Article
- Unnatural Amino Acid and Emerging Chemistry Approaches to Map RNA-Protein Interactions.Angewandte Chemie (International ed. in English) · 2026Review
- Diazirines Beyond Photoaffinity Labeling: A Comprehensive Overview of Applications in Biological Sciences, Materials Chemistry, and NMR-Spectroscopy.Angewandte Chemie (International ed. in English) · 2026Review
- Covalent Probes Reveal Small-Molecule Binding Pockets in Structured RNA and Enable Bioactive Compound Design.Journal of the American Chemical Society · 2025Article
- Polymerization-Induced Direct Photolithography of Quantum Dots.Macromolecular rapid communications · 2025Review
- The Versatility of Diazirines: Properties, Synthetic and Modern Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Optimal Wavelengths and Solvents to Modulate Diazirine Kinetics.ACS omega · 2025Article
- Single-Carbon Insertion into Single C-C Bonds with Diazirines.Journal of the American Chemical Society · 2025Article
- Dissecting diazirine photo-reaction mechanism for protein residue-specific cross-linking and distance mapping.Nature communications · 2024Article
- Hydrophilic Photocrosslinkers as a Universal Solution to Endow Water Affinity to a Polymer Photocatalyst for an Enhanced Hydrogen Evolution Rate.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Tougher Bioadhesives through Dual Stimulation Strategies.Advanced healthcare materials · 2024Article
- Dynamic Chemistry Toolbox for Advanced Sustainable Materials.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Review
- Diazirine-Functionalized Polyurethane Crosslinkers for Isocyanate-Free Curing of Polyol-Based Coatings.ACS applied polymer materials · 2024Article
- Trifluoroethylation and Pentafluoropropylation of C(spChemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Methylene Insertion into Nitrogen-Heteroatom Single Bonds of 1,2-Azoles via a Zinc Carbenoid: An Alternative Tool for Skeletal Editing.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Diazirine reagents allow for the ready generation of carbenes upon photochemical, thermal, or electrical stimulation. Because carbenes formed in this way can undergo rapid insertion into any nearby C-H, O-H or N-H bond, molecules that encode diazirine functions have emerged as privileged tools in applications ranging from biological target identification and proteomics through to polymer crosslinking and adhesion. Here we use a combination of experimental and computational methods to complete the first comprehensive survey of diazirine structure-function relationships, with a particular focus on thermal activation methods. We reveal a striking ability to vary the activation energy and activation temperature of aryl diazirines through the rational manipulation of electronic properties. Significantly, we show that electron-rich diazirines have greatly enhanced efficacy toward C-H insertion, under both thermal and photochemical activation conditions. We expect these results to lead to significant improvements in diazirine-based chemical probes and polymer crosslinkers.
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Registered trials
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