Cross-linked peptidomimetic films generated by azide-alkyne cycloadditions on a solid copper surface

ORGN 576

Neel H. Shah, neel@nyu.edu and Kent Kirshenbaum, kent@nyu.edu. Department of Chemistry, New York University, 100 Washington Square East, Room 1001, New York, NY 10003-6688
N-substituted glycine oligomers, or “peptoids,” are a class of biomimetic molecules which can be efficiently synthesized to incorporate a diverse range of side-chains in a sequence-specific manner. The versatility and synthetic ease of these molecules make them suitable candidates for a wide range of materials applications. Here, we demonstrate the use of peptoids in conjunction with the copper-catalyzed [3+2] cycloaddition of azides and alkynes to generate branched polymer networks. It is shown that by incorporating both azides and alkynes onto the molecular scaffold, peptoids can form cross-linked macromolecules in the presence of copper. Furthermore, by attaching a thiourea group onto the oligomer, these molecules can be localized onto a copper metal surface, allowing for increased network proliferation which in turn generates macroscopic films. This novel procedure provides a direct method for the chemical modification of metal surfaces.