Phosphonioalkylthiosulfate zwitterions - new masked thiol ligands for the formation of cationic functionalised gold nanoparticles

Ju-Nam, Y., Bricklebank, N., Allen, D.W., Gardiner, P.H.E., Light, M.E. and Hursthouse, M.B. (2006) Phosphonioalkylthiosulfate zwitterions - new masked thiol ligands for the formation of cationic functionalised gold nanoparticles. Organic & Biomolecular Chemistry, 4 (23), 4345-4351. (doi:10.1039/b610480k).

Abstract

We report the synthesis and structural characterisation of a new family of stable phosphonioalkylthiosulfate zwitterions, R3P+(CH2)(n)S2O3- (R = Ph or Bu, n = 3,4,6, 8 or 10) which behave as cationic masked thiolate ligands with applications in the functionalisation of gold nanoparticles, having potential as new diagnostic biorecognition systems. The ligands were prepared by treatment of omega-bromoalkylphosphonium salts with sodium thiosulfate. The crystal and molecular structures of the zwitterions (R = Ph, n = 3) and ( R = Bu, n = 3) were determined. A series of phosphonioalkanethiolate-capped gold nanoparticles dispersed in water was prepared by borohydride reduction of potassium tetrachloroaurate in the presence of the zwitterions in a dichloromethane-water system. UV-visible spectroscopy and scanning transmission electron-microscopy indicated that capped nanoparticles of ca. 5 nm diameter were present.

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Contributors

Author: M.E. Light

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