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Silica-attached molecular receptor complexes for benzoates and naphthoates

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Abstract

A series of cyclen (1,4,7,10-tetraazacyclododecane) derived molecular receptors for aromatic oxoanions, that are activated by complexation with Cd(II), have been covalently linked to 3-(glycidoxy)propyl-functionalised silica gel (70–230 mesh). These immobilised receptor complexes are highly effective for the sequestration of o-hydroxybenzoates and 2-naphthoate from aqueous solution, achieving a >80% saturation level by stirring the material in the aqueous solution for 1 h at pH 7.00 and 298 K. Examination of the uptake levels of a variety of different benzoates and naphthoates suggests that the retention mechanism involves a combination of classical hydrogen bonding and non-classical, water mediated, O–H···π hydrogen bonding. Contrary to expectations, attachment of hydroxy terminated polyether chains to the periphery of the receptor complex diminished the level of uptake.

Graphical synopsis

Silica-attached receptor complexes of the type shown are effective materials for sequestering o-hydroxybenzoates from aqueous solution.

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Acknowledgement

We are grateful to the Australian Research Council for the support of this work.

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Authors and Affiliations

  1. School of Chemistry, Physics and Earth Sciences, Flinders University, GPO Box 2100, Adelaide, SA, 5001, Australia

    Jozef A. Z. Hodyl & Kevin P. Wainwright

  2. School of Chemistry and Physics, University of Adelaide, Adelaide, SA, 5005, Australia

    Stephen F. Lincoln

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  1. Jozef A. Z. Hodyl
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  2. Stephen F. Lincoln
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  3. Kevin P. Wainwright
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Correspondence to Kevin P. Wainwright.

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Hodyl, J.A.Z., Lincoln, S.F. & Wainwright, K.P. Silica-attached molecular receptor complexes for benzoates and naphthoates. J Incl Phenom Macrocycl Chem 68, 261–270 (2010). https://doi.org/10.1007/s10847-010-9782-8

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