Over the last twenty years, Self Assembled Monolayers (SAMs) have been widely used to control surface properties in various research fields primarily using thiols and disulfides.
The sulfur atom from the thiol group is able to assemble molecules to surfaces, such as gold. A pre-determined head group can also be displayed.
Example applications include: a) non-foluing surfaces b) SAMs with specific binding receptors c) cell supports for native cell growth d) molecular electronics e) microarrays and f) separations.
In situ deprotection of thioacetates affords a solution to some of the current challenges. Thioacetates can be prepared in high purities, and remain stable for extended periods of time. They can be deprotected using relatively mild conditions to generate high purity thiols. These thiols can then begin to assemble immediately, forming highly-organized self-assembled monolayers.
The following deprotection procedure was used to obtain 11-Mercapto-1-undecene in 86% yield. The thiol was then passed through a silica gel pad to provide high purity (>99%) materials for SAMs.