The synthesis and characterisation of masked phosphonioalkyl selenoates: potential ligands for the production of functionalised gold nanoparticles

Ju-Nam, Y., Allen, D.W., Gardiner, P.H.E., Light, M.E., Hursthouse, M.B. and Bricklebank, N. (2007) The synthesis and characterisation of masked phosphonioalkyl selenoates: potential ligands for the production of functionalised gold nanoparticles. Journal of Organometallic Chemistry, 692 (22), 5065-5070. (doi:10.1016/j.jorganchem.2007.07.038).

Abstract

Two new masked phosphonioalkylselenoate ligands, bis(3-triphenylphosphoniopropyl)diselenide- and 6-(selenocyano)hexyl-triphenylphosphonium-selenocyanates, have been prepared. The molecular structure of the bis(3-triphenylphosphoniopropyl)diselenide diselenocyanate has been determined by X-ray crystallography. The structure reveals an overall stoichiometry of {[Ph3P+(CH2)3Se]2(SeCN?)2 · KOH}, with the bis(3-triphenylphosphoniopropylselenium)diselenocyanate units arranged in pairs around an inversion centre. The potassium ion is disordered over several positions but its main component forms a near linear KSe contact to one of the selenium atoms in the diselenide bond. The hexyl derivative, 6-(selenocyano)hexyl-triphenylphosphonium selenocyanate forms as a yellow oil that was characterised spectroscopically. Both phosphonioalkylselenide cations undergo reductive cleavage to form phosphonioalkylselenoate zwitterions. Attempts to prepare phosphonioalkylselenoate-functionalised gold nanoparticles in situ through the NaBH4-promoted reduction of tetrachloroaurate salts in a water/dichloromethane biphasic system are also described.

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Contributors

Author: M.E. Light

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