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Research Article

Reactivity of Acid Fluoride-Terminated Self-Assembled Monolayers on Gold

Young Shik Chi,^† Kyung-Bok Lee,^‡ Yongseong Kim,^§ and Insung S. Choi*^†

Department of Chemistry and School of Molecular Science (BK21), Center for Molecular Design and Synthesis, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Korea, Glycomics Team, Korea Basic Science Institute (KBSI), Daejeon 305-333, Korea, and Department of Chemistry, Division of Natural Sciences, Kyungnam University, Masan 631-701, Korea

Langmuir, 2007, 23 (3), pp 1209–1214

DOI: 10.1021/la061878s

Publication Date (Web): December 9, 2006

†

KAIST.

‡

KBSI.

Kyungnam University.

To whom correspondence should be addressed. E-mail: ischoi@ kaist.ac.kr.

Abstract

This report describes the reactivity of acid fluoride (AF)-terminated self-assembled monolayers (SAMs) on gold toward amine and alcohol compounds and the potentiality of AF as a reactive intermediate for surface functionalizations. The AF group was generated in situ on a gold surface by reacting the terminal carboxylic acid group in the SAM of 16-mercaptohexadecanoic acid with cyanuric fluoride and pyridine under the optimized conditions. AF was found to be highly reactive toward various amine groups, such as primary and secondary amines, but it did not react effectively with alcohol. In addition, the amide coupling reaction by microcontact printing (μCP) was compared with the solution-based reaction: when amine-derivatized ferrocene compound was used for 1-min μCP on the AF-activated surface, the surface coverage of the reaction product was about 83% of 3.45 × 10¹⁴ cm^-2, the coverage obtained in the solution-based reaction. On the basis of the high reaction efficiency of μCP, the AF-activated surface was also used as a platform for patterning a biological ligand, biotin.

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History

Published In Issue January 30, 2007
Received June 29, 2006
Revised October 26, 2006

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Research Article

Reactivity of Acid Fluoride-Terminated Self-Assembled Monolayers on Gold