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
StatePublished - Jun 1 2013

Fingerprint

Amphiphiles
Self assembled monolayers
bioinstrumentation
Biosensors
Monolayers
Electrochemical sensors
synthesis
Benzene
Sulfhydryl Compounds
Acetic Acid
cross sections
acetic acid
thiols
benzene
sensors

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Design and synthesis of a class of twin-chain amphiphiles for self-assembled monolayer-based electrochemical biosensor applications. / Fisher, Thomas J.; Cañete, Socrates Jose P.; Lai, Rebecca Y.; Dussault, Patrick H.

In: European Journal of Organic Chemistry, No. 16, 01.06.2013, p. 3263-3270.

Research output: Contribution to journalArticle

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