Chemical surface reactions by click chemistry: coumarin dye modification of11-bromoundecyltrichlorosilane monolayers

Abstract

The functionalization of surfaces and the ability to tailor their properties with desiredphysico-chemical functions is an important field of research with a broad spectrum ofapplications. These applications range from the modification of wetting properties, over thealteration of optical properties, to the fabrication of molecular electronic devices. In each ofthese fields, it is of specific importance to be able to control the quality of the layers withhigh precision. The present study demonstrates an approach that utilizes the 1,3-dipolarcycloaddition of terminal acetylenes to prepare triazole-terminated monolayerson different substrates. The characterization of the precursor monolayers, theoptimization of the chemical surface reactions as well as the clicking of a fluorescent dyemolecule on such azide-terminated monolayers was carried out. A coumarin 343derivative was utilized to discuss the aspects of the functionalization approach.Based on this approach, a number of potential surface reactions, facilitated viathe acetylene-substituted functional molecules, for a broad range of applicationsis at hand, thus leading to numerous possibilities where surface modificationsare concerned. These modifications can be applied on non-structured surfaces ofsilicon or glass or can be used on structured surfaces. Various possibilities arediscussed.