Diazo transfer on material surfaces: a novel method for azido functionalisation

Preparation of azido-functionalized polymers is gaining increasing attention. We wish to report an innovative, novel strategy for azido functionalization of polymeric materials, coupling plasma technology and solution processed diazo transfer reactions. This novel approach allows the azido group to be introduced downstream of the material preparation, thus preserving its physicochemical and mechanical characteristics, which can be tailored a priori according to the desired application. The whole process involves the surface plasma functionalization of a material with primary amino groups, followed by a diazo transfer reaction, which converts the amino functionalities into azido groups that can be exploited for further chemoselective reactions. The diazo transfer reaction is performed in a heterogeneous phase, where the azido group donor is in solution. Chemical reactivity of the azido functionalities was verified by subsequent copper-catalyzed azide-alkyne cycloaddition. © 2011 Elsevier Ltd.