Trichlorosilane Isocyanate as Coupling Agent for Mild Conditions Functionalization of Silica-Coated Surfaces

Abstract

Despite the importance of the isocyanate group in chemistry, very few examples of isocyanate-modified silicas have been reported, and all of the strategies described so far led to partial or total hydrolysis or condensation of the isocyanate group. By synthesizing trichlorosilane isocyanate as the coupling reagent, we show that oxidized silicon wafers are successfully modified with the isocyanate group. Our method is achieved in mild conditions, at low temperature, without side-reactions and allows the formation of a self-assembled monolayer (SAM) of isocyanates. The isocyanate group then offers a flexible way to further functionalize silica substrates with different nucleophiles, due to its high and specific reactivity.

Reaction of Isocyanate‐Functionalised Silicon Wafers with Complex Amino Compounds

“…Having substrates 1-4 in our hands, we could attempt the preparation of isocyanate-terminated silicon wafers that were proposed to be utilised in the following immobilisation of the above-mentioned amino compounds. Such a surface was prepared as described previously: [8] a single silicon wafer crystal (100) with a silica layer of 1.8-2 nm thickness at the surface was treated with a solution of 10-isocyanatodecyltrichlorosilane in 1,1,2-trichloroethene in the presence of iPr 2 NEt at 0°C to complete the surface modification within 50 min (Scheme 2). The reaction progress was monitored by ATR FTIR (Figure 3).…”

“…[8] To explore the scope and limitations of our methodology, we turned to more complex molecules to be attached to the surface. Herein, we report the reaction of isocyanate-functionalised silicon wafers with biomolecules and an unnatural aromatic amino compound.…”

“…(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) sembled monolayer of an isocyanate species on a silicon oxide surface and, moreover, we have shown the versatility of this modified surface for the covalent attachment of different simple nucleophiles as aliphatic/aromatic thiols, amines and phenols. [8] To explore the scope and limitations of our methodology, we turned to more complex molecules to be attached to the surface. Herein, we report the reaction of isocyanate-functionalised silicon wafers with biomolecules and an unnatural aromatic amino compound.…”

Fundamental studies in nanosciences at the Institute of Electronics, Microelectronics, and Nanotechnology (IEMN)

“…On these supports, generally consisting of a Si substrate, we characterise the immobilisation of biological probes, which are linked by chemioselective methods developed at the Institut of Biology in Lille (IBL) [32]. Along with these characterisations, we understand the physical mechanisms ruling the behaviour of a liquid in nanostructured supports and find out solutions in the design of new nanostructures which enhance the optical signal emitted by the optical biological receptors adsorbed on the Si supports [33][34][35][36].…”

Fluoroalkylsilane versus Alkylsilane as Hydrophobic Agents for Silica and Silicates

“…Modification significantly extends the range of application of a given silica-based filler. Modified silicates with reduced wettability are used in the construction of sunlight collectors, elements of touch panels for optical and other devices used in industry, and motor vehicles and household utensils and also in the production of new types of textile products [37,38].…”