Applications, properties and synthesis of ω-functionalized n-alkanethiols and disulfides - The building blocks of self-assembled monolayers

Dariusz Witt, Rafal Klajn, Piotr Barski, Bartosz A. Grzybowski

Research output: Contribution to journalArticle

170 Citations (Scopus)

Abstract

Self-assembled monolayers (SAMs) of alkane thiols on gold and other metals are versatile constructs with which to study interfacial phenomena and reactions at surfaces. Surface properties of SAMs - e.g., wettability, stability in diverse environments, propensity to interact with or to resist adsorption of macromolecules - depend on and can be controlled flexibly by the properties of the functional (head) groups in the ω position of the alkyl chain. SAMs provide a basis for many important scientific and technological applications, ranging from micropatterning methods,through sensing,to biological recognition. Despite their importance, the literature on SAMs and the synthesis of molecules that constitute them remains scattered and often conflicting. The purpose of this Review is (i) to summarize the applications and physical properties of SAMs and (ii) to systematize the strategies of synthesis of ω-functionalized alkane thiols. Generic retrosynthetic scheme is developed that allows efficient synthetic planning. Issues related to the selection of appropriate protecting groups and the ways of introduction of the thiol functionality are discussed in detail, and illustrated with examples of syntheses of several complex alkane thiols.

Original languageEnglish
Pages (from-to)1763-1797
Number of pages35
JournalCurrent Organic Chemistry
Volume8
Issue number18
DOIs
Publication statusPublished - Dec 2004

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Self assembled monolayers
Disulfides
Sulfhydryl Compounds
Alkanes
Macromolecules
Gold
Surface properties
Wetting
Physical properties
Metals
Adsorption
Planning
Molecules

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Applications, properties and synthesis of ω-functionalized n-alkanethiols and disulfides - The building blocks of self-assembled monolayers. / Witt, Dariusz; Klajn, Rafal; Barski, Piotr; Grzybowski, Bartosz A.

In: Current Organic Chemistry, Vol. 8, No. 18, 12.2004, p. 1763-1797.

Research output: Contribution to journalArticle

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