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

✍ Scribed by Bassam M. Nakhle; Scott A. Trammell; Keith M. Sigel; Thomas J. Meyer; Bruce W. Erickson

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 780 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00062-9

✦ Synopsis

A protected form of 3,5-bis(phosphonomethyl)benzoic avid (Bpb-OH), a metal oxide surface bivalent anchor, has been synthesized, coupled to an amine functionality, deproteeted, 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 prefine-chromophore, delmatected with a solution of indotrimethylsilane (I'MSI) in acetonitrile and adsorbed to Tin(IV) doped indium oxide and nanocrystalline TiO 2 electedes at surface coverages of 1.5 x 10 -10 tool cm "2 and 4.9 x 10 "11 mol era -2, respectively. Finally, Me4Bpb-OH was converted to an amino derivative by attaching a diamino butane linker.