3 years ago

Malonic Acid Diazoesters for C−H Insertion Crosslinking (CHic) Reactions: A Versatile Method for the Generation of Tailor-Made Surfaces

Malonic Acid Diazoesters for C−H Insertion Crosslinking (CHic) Reactions: A Versatile Method for the Generation of Tailor-Made Surfaces
Philip F. Kotrade, Jürgen Rühe
A simple and versatile method for the modification of a broad spectrum of surfaces with thin polymer films through the thermally or photochemically induced generation of surface-attached polymer networks is reported. The system is based on copolymers containing diazomalonate groups, which can be activated by heat or light. To this end, the copolymers are deposited from solution onto solid substrates by standard techniques of thin-film deposition (spin coating, dip coating). Upon activation the diazomalonate group decomposes and forms a carbene, which induces C−H insertion crosslinking (CHic) reactions. In the course of this process network formation and covalent surface attachment occur at the same time. The crosslinking process proceeds very rapidly, especially when the carbenes generated in the activation process cannot undergo Wolff-rearrangement. The presented system can be used for the generation of a wide range of polymer layers and microstructures on a broad spectrum of surfaces. Polymer networks generated by means of C−H insertion reactions, from copolymers containing diazomalonate groups, allow a simple and versatile modification of a broad range of materials. For example, tailor-made surfaces can be obtained that allow simple immobilization of DNA or proteins for use in microarrays or immunoassays.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201704486

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