Preparations of Universal, Functionalized Long-Chain Alkylthiol Linkers for Self-assembled Monolayers

Abstract

In this research, the preparation processes for making a series of ω-mercapto alkylamine 1 and ω-mercapto alkanoic acid 2 useful for studying of the self-assembled monolayer(SAM) are described. The preparation methods of the first goal materials, ω-mercapto alkylamines 1 were carried out as follows: First, ω-phthalimide alkanol 3 was synthesized from commercially available potassium phthalimide derivatives and ω-bromoalkanol in DMF at 80 o C via substitution reaction. After refluxing ω-phthalimide alkanol 3 with hydrazine hydrate in ethanol followed by treating with c-HCl, ω-aminoalkanol 4 was obtained in 76~98% yield, accompanied with side-product 5. Bromination of hydroxyl moiety of ω-aminoalkanol 4 using aqueous hydrobromic acid furnished ω-bromoamine 6 in 34~97% yields. Substitution reaction 6 with thiourea in 95% ethanol gave ω-aminoalkanthiuronium 7, which was treated with aqueous † To whom correspondence should be addressed.