The robust electrochemical vinylation of carbon surfaces

Philippe Poizot (1) , Jacques Simonet (2)

1 LRCS - Laboratoire réactivité et chimie des solides - UMR CNRS 7314
2 ISCR - Institut des Sciences Chimiques de Rennes

A facile immobilization method of vinyl groups onto glassy carbon is described using ω-bromo-1-alkenes as model substrates. The process is based on the cathodic charging of the carbon electrode at E < − 2 V vs. Ag/AgCl performed in organic polar solvents containing tetraalkylammonium salts. This cathodic charging of carbons permits the SN displacement of the bromide out of bromo-alkenes and leads to a thorough surface coating with a thin layer of unsaturated chain. The surfacial level of vinylation (~ 5 × 10− 9 mol cm− 2) was efficiently estimated by means of bromine and iodine indexes. Additionally, the efficiency of this halogen addition reaction to the alkene functional group was confirmed by EDS measurements

Mots clés: Glassy carbon; Surface modification; Grafting of vinylic chains; Halo 1-alkenes

Domaines: Chimie organique

Philippe Poizot, Jacques Simonet. The robust electrochemical vinylation of carbon surfaces. Electrochemistry Communications, 2012, 23, pp.137-140. ⟨10.1016/j.elecom.2012.07.010⟩. ⟨hal-00725258⟩