Elsevier

Tetrahedron

Volume 55, Issue 10, 5 March 1999, Pages 2835-2846
Tetrahedron

Synthesis of 3,5-bis(phosphonomethyl)benzoic acid and its application as a metal oxide surface bivalent anchor

Dedicated to the memory of Professor Bruce W. Erickson
https://doi.org/10.1016/S0040-4020(99)00062-9Get rights and content

Abstract

A protected form of 3,5-bis(phosphonomethyl)benzoic acid (Bpb-OH), a metal oxide surface bivalent anchor, has been synthesized, coupled to an amine functionality, deprotected, and shown to bind to metal oxide surfaces. The protected anchor, 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid (Me4Bpb-OH) was synthesized in 23% yield over four steps, coupled to a proline-chromophore, deprotected with a solution of iodotrimethylsilane (TMSI) in acetonitrile and adsorbed to Tin(IV)-doped indium oxide and nanocrystalline TiO2 electodes at surface coverages of 1.5 × 10−10 mol cm−2 and 4.9 × 10−11 mol cm−2, respectively. Finally, Me4Bpb-OH was converted to an amino derivative by attaching a diamino butane linker.

A protected form (1) of 3,5-bis(phosphonomethyl)benzoic acid (2) has been synthesized, coupled to a proline-chromophore, deprotected, and adsorbed to a metal oxide surface.

  1. Download : Download full-size image

References (22)

  • M. Engel et al.

    Tetrahedron

    (1993)
  • D.G. McCafferty et al.

    Tetrahedron

    (1995)
  • C.E. McKenna et al.

    Tetrahedron Lett.

    (1977)
  • G.A. Olah et al.

    Tetrahedron

    (1982)
  • A. Otaka et al.

    Tetrahedron Lett.

    (1993)
  • J. Wrobel et al.

    Tetrahedron Lett.

    (1993)
  • D.G. McCafferty et al.

    Tetrahedron

    (1995)
  • N. Vlachopoulos et al.

    J. Am. Chem. Soc.

    (1988)
  • B. O'Reagan et al.

    Nature

    (1991)
  • T.J. Meyer et al.

    Inorg. Chem.

    (1994)
  • S.M. Zakeeruddin et al.

    Inorg. Chem.

    (1997)
  • Cited by (0)

    View full text