One-step photochemical attachment of NHS-terminated monolayers onto silicon surfaces and subsequent functionalization.
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.
Yang
Menglong
M
Laboratory of Organic Chemistry, Wageningen University and Research Center, Dreijenplein 8, 6703 HB Wageningen, The Netherlands.
Teeuwen
Rosalie L M
RL
Giesbers
Marcel
M
Baggerman
Jacob
J
Arafat
Ahmed
A
de Wolf
Frits A
FA
van Hest
Jan C M
JC
Zuilhof
Han
H
D001710:Biotin / Q000031:analogs & derivatives / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D018625:Microscopy, Atomic Force; D015394:Molecular Structure; D010777:Photochemistry; D012825:Silicon / Q000737:chemistry*; D013057:Spectrum Analysis; D013388:Succinimides / Q000737:chemistry*; D013499:Surface Properties
D004952:Esters; D013388:Succinimides; C053311:biotin hydrazide; D001710:Biotin; C001426:N-hydroxysuccinimide; D012825:Silicon