Design and synthesis of a class of twin-chain amphiphiles for self-assembled monolayer-based electrochemical biosensor applications

A new class of twin-chain hydroxyalkylthiols (mercaptoalkanols) is described that features a nearly constant cross section and the potential for modification at one or both termini. These compounds are regioselectively available through Pd-mediated couplings of benzene diiododitriflate, and their syntheses include an example of a previously unreported coupling reaction to generate an ortho-substituted arene bis(acetic acid). In an electrochemical sensor system, the self-assembled monolayers (SAMs) that were prepared from the new amphiphiles demonstrate an improved stability in comparison to the monolayers prepared from analogous single-chain thiols. A new class of twin-chain hydroxyalkylthiols (mercaptoalkanols) is described that features a constant cross section and the potential for modification at one or both termini. Under conditions for surface electrochemical sensing, these derived monolayers displayed greater stability than the self-assembled monolayers (SAMs) that were prepared from analogous single-chain amphiphiles.