Simple Chemical Modification Using Perfluoroalkyl‐Substituted Stable Nitrile N‐Oxide on Bulk Surface via Catalyst‐Free Click Reaction

Fluorinated surfaces show favorable physical properties for material applications. However, fluorination processes of bulk surfaces using conventional reagents require skilled techniques and special equipment. Herein, we demonstrate highly efficient surface modification using a new fluorination tool, perfluoroalkyl‐substituted stable nitrile N‐oxide. The nitrile N‐oxide is successfully synthesized in one‐pot by exploiting 1,1‐diphenylnitroethene as the precursor of nitrile N‐oxide. The nitrile N‐oxide exhibits not only high reactivity but also thermal stability, which enables the simple chemical modification of allyl group‐modified rigid surfaces without catalysts or byproducts. The surface is analysed by X‐ray photoelectron spectroscopy, time‐of‐flight secondary ion mass spectrometry, and contact angle measurements, providing clear evidence that the perfluoroalkyl groups are densely integrated on the bulk surface as a result of the efficient covalent bond formation. A perfluoroalkyl group‐containing stable nitrile N‐oxide is synthesized in one‐pot. The nitrile N‐oxide exhibits not only high reactivity but also thermal stability, enabling direct fluorination of olefin‐modified glass surfaces through a catalyst‐ and solvent‐free click reaction. The fluorinated surface is characterized by X‐ray photoelectron spectroscopy, time‐of‐flight secondary ion mass spectrometry, and contact angle measurements.