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 language | English |
|---|---|
| Pages (from-to) | 1763-1797 |
| Number of pages | 35 |
| Journal | Current Organic Chemistry |
| Volume | 8 |
| Issue number | 18 |
| DOIs | |
| Publication status | Published - Dec 2004 |
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ASJC Scopus subject areas
- Organic Chemistry
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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 journal › Article
}
TY - JOUR
T1 - Applications, properties and synthesis of ω-functionalized n-alkanethiols and disulfides - The building blocks of self-assembled monolayers
AU - Witt, Dariusz
AU - Klajn, Rafal
AU - Barski, Piotr
AU - Grzybowski, Bartosz A.
PY - 2004/12
Y1 - 2004/12
N2 - 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.
AB - 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.
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U2 - 10.2174/1385272043369421
DO - 10.2174/1385272043369421
M3 - Article
VL - 8
SP - 1763
EP - 1797
JO - Current Organic Chemistry
JF - Current Organic Chemistry
SN - 1385-2728
IS - 18
ER -