Versatile Method for Chemical Reactions with Self-Assembled Monolayers of Alkanethiols on Gold

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• 作者：Henrik H. J. Persson ; Walter R. Caseri ; and Ulrich W. Suter
• 刊名：Langmuir
• 出版年：2001
• 出版时间：June 12, 2001
• 年：2001
• 卷：17
• 期：12
• 页码：3643 - 3650
• 全文大小：118K
• 年卷期：v.17,no.12(June 12, 2001)
• ISSN：1520-5827

文摘

Self-assembled monolayers (SAMs) of 11-mercapto-1-undecanol (TOH) and mixed monolayers of TOHand dodecanethiol (TCH₃) were transformed to isocyanate-bearing layers by reaction of the hydroxyl groupsin the monolayers and mixed layers with 1,4-phenylene diisocyanate (PDI). PDI reacts with only one ofits isocyanate groups, yielding a carbamate (urethane) group; conversion of the hydroxyl groups is nearlyquantitative, and the attached phenylene isocyanate moiety is oriented perpendicularly to the surface, asindicated by IR reflection measurements at grazing incidence. The free isocyanate groups readily reactunder mild conditions with a variety of substances, for example, water, alcohols, and amines. Hence, theconversion of surface hydroxyl groups with PDI offers a versatile and straightforward method to modifysurfaces and to facilitate further reactions with additional compounds.