One-Step Photochemical Attachment of NHS-Terminated Monolayers onto Silicon Surfaces and Subsequent Functionalization

Citations Over TimeTop 10% of 2008 papers

Abstract

N-Hydroxysuccinimide (NHS)-ester-terminated monolayers were covalently attached in one step onto silicon using visible light. This mild photochemical attachment, starting from omega-NHS-functionalized 1-alkenes, yields a clean and flat monolayer-modified silicon surface and allows a mild and rapid functionalization of the surface by substitution of the NHS-ester moieties with amines at room temperature. Using a combination of analytical techniques (infrared reflection absorption spectroscopy (IRRAS), extensive X-ray photoelectron spectroscopy (XPS) in combination with density functional theory calculations of the XPS chemical shifts of the carbon atoms, atomic force microscopy (AFM), and static contact angle measurements), it was shown that the NHS-ester groups were attached fully intact onto the surface. The surface reactivity of the NHS-ester moieties toward amines was qualitatively and quantitatively evaluated via the reaction with para-trifluoromethyl benzylamine and biotin hydrazide.

Related Papers

• Self-assembled monolayers of thiols(1998)
• → Stabilization of Langmuir monolayer of hydrophobic thiocholesterol molecules(2008)8 cited
• → Mixed SAMs of backbone-functionalized tribenzotriquinacenes and alkanethiols: Synthesis, preparation and STM-investigations(2015)10 cited
• CYCLIC VOLTAMMETRY STUDY OF SELF-ASSEMBLED LAYER ON SILVER(2006)
• Formation process and topography characteristics of OTS self-assembled monolayers(2002)