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

Thomas J. Fisher, Socrates Jose P. Cañete, Rebecca Y. Lai, Patrick H. Dussault

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3263-3270
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
Publication statusPublished - Jun 1 2013

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Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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