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

Bassam M. Nakhle, Scott A. Trammell, Keith M. Sigel, Thomas J. Meyer, Bruce W. Erickson

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

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 electrodes at surface coverages of 1.5 x 10-10 mol cm-2 and 4.9 x 10-11 mol cm-2, respectively. Finally, Me4Bpb-OH was converted to an amino derivative by attaching a diamino butane linker.

Original languageEnglish
Pages (from-to)2835-2846
Number of pages12
JournalTetrahedron
Volume55
Issue number10
DOIs
StatePublished - 5 Mar 1999
Externally publishedYes

Keywords

  • Electron transfer
  • Metals
  • Phosphonic acids and derivatives
  • Photochemistry

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