Design and Synthesis of a New Class of Twin-Chain Amphiphiles for Self-Assembled Monolayer-based Electrochemical Biosensor Applications.

A new class of twin-chain hydroxyalkylthiols (mercaptoalkanols) featuring a nearly constant cross-section and the potential for modification of one or both termini are available with complete regioselectivity through Pd-mediated couplings of benzene diiododitriflate, including an example of a previously unreported coupling to generate an ortho-substituted arene bis acetic acid. Self-assembled monolayers (SAMs) prepared from the new amphiphiles demonstrate improved stability in an electrochemical sensor system compared with monolayers prepared from analogous single chain thiols.