Conversion of a glycidyl methacrylate resin into a thiirane analogue and subsequent immobilisation of aliphatic amine and azole ligands

Abstract

A facile and high yielding conversion of poly[(glycidyl methacrylate)-co-(ethane-1,2-diyl dimethacrylate)] macro-porous resin into its sulfur-containing thiirane analogue has been developed. The most favourable procedure involves reaction at room temperature of thiourea in water catalysed by dilute sulfuric acid. Resins containing up to 3 mmol g ^–1 of thiirane groups are readily prepared. The resultant thiirane resins are very reactive, and in particular a range of simple aliphatic amines and azoles have been immobilised via ring-opening of the thiirane ring. Toluene has been shown to be the best solvent of those examined, and in this case the reaction is clean, generating 1 mol of thiol group for every azole attached, in keeping with the simple mechanistic picture.

The novel thiirane-containing porous resin material offers great scope for further ingenious modification, and the ease of synthesis of the resin suggests that it will be widely exploited in the future.