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

M. Yang, R.L.M. Teeuwen, M. Giesbers, J. Baggerman, A. Arafat, F.A. de Wolf, J.C.M. van Hest, H. Zuilhof

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66 Citations (Scopus)

Abstract

N-Hydroxysuccinimide (NHS)-ester-terminated monolayers were covalently attached in one step onto silicon using visible light. This mild photochemical attachment, starting from ¿-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.
Original languageEnglish
Pages (from-to)7931-7938
JournalLangmuir
Volume24
Issue number15
DOIs
Publication statusPublished - 2008

Keywords

  • self-assembled monolayers
  • extremely mild attachment
  • organic monolayers
  • visible-light
  • nitride surfaces
  • porous silicon
  • immobilization
  • alkyl
  • dna
  • acid

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