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

作者：Fisher Thomas J; Canete Socrates Jose P; Lai Rebecca Y; Dussault Patrick H^*

来源：European Journal of Organic Chemistry, 2013, 2013(16): 3263-3270.

DOI：10.1002/ejoc.201201732

• Amphiphiles
• Sensors
• Self-assemby
• Arenes
• Sulfur
• Cross-coupling

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.

• 出版日期2013-6