Interfacial modification of silica surfaces through γ-isocyanatopropyl triethoxy silane–amine coupling reactions

The development of robust, cost-effective methods to modify surfaces and interfaces without the specialized synthesis of unique coupling agents could provide readily accessible routes to optimize and tailor interfacial properties. We demonstrate that γ-isocyanatopropyl triethoxysilane (ISO) provides a convenient route to functionalize silica surfaces through coupling reactions with readily available reagents. ISO coupling agents layers (CALs) can be prepared from toluene with triethylamine (TEA), but the coupling reaction of an amine to the ISO CAL does not proceed. We use near edge X-ray absorption fine structure (NEXAFS), time-of-flight secondary ion mass spectrometry (TOF-SIMS) and sessile drop contact angle to demonstrate the isocyanate layer is not degraded under coupling conditions. Access to silanes with chemical functionality is possible with ISO by performing the coupling reaction in solution and then depositing the product onto the surface. Two model CAL surfaces are prepared to demonstrate the ease and robust nature of this procedure. The surfaces prepared using this method are the ISO reacted with octadecylamine to produce a hydrocarbon surface of similar quality to octadecyl trichlorosilane (OTS) CALs and with 9-aminofluorene (AFL), an aromatic amine functionality whose silane is otherwise unavailable commercially.