B. Nakhle, S. Trammell, K. Sigel
Mar 5, 1999
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron
Abstract
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 (Me 4 Bpb-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 TiO 2 electodes at surface coverages of 1.5 × 10 −10 mol cm −2 and 4.9 × 10 −11 mol cm −2 , respectively. Finally, Me 4 Bpb-OH was converted to an amino derivative by attaching a diamino butane linker.