A carbene insertion approach to functionalised poly(ethylene oxide)-based gels

Carbenes photogenerated from the novel bisdiazirine, 1,3-bis(3-(trifluoromethyl)diazirin-3-yl)benzene 1, have been applied successfully to cross-linking of mono-methyl poly(ethylene oxide) (MePEO5000) in the presence of dichloromethane, leading to the simultaneous incorporation of alkylhalide functionalities. The PEO-based gels swell in a wide range of solvents with polarity index values varying from 3.1 to 9.0. Reaction of the alkylhalide functionalities present in the gels with 4-phenylazophenol provided loading capacities of up to 0.20 mmol g−1 and demonstrated the potential of these materials for gel-phase synthesis applications.