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Water-soluble β-aminobisulfonate building blocks for pH and Cu2+ indicators

Lookup NU author(s): Dr Ulrich Baisch, Professor Mike ProbertORCiD

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Abstract

Two water-soluble phenyl beta-aminobisulfonate ligands were synthesised and characterised by spectroscopic techniques including UV-visible absorption, electron paramagnetic resonance (EPR) and H-1 NMR spectroscopy. The acid-base and complexometric binding properties were studied in water and methanol, respectively. Single crystal X-ray crystallography was used to elucidate the solid-state properties. The pK(a)s of the phenyl beta-aminobisulfonate 1 and methoxyphenyl b-aminobisulfonate 2 were evaluated to be 3.1 and 4.4, respectively. UV-visible, EPR and NMR spectroscopy provide direct evidence for complexation of 2 with Cu2+ in methanol due to coordination with the pendant methoxy moiety. The EPR and NMR data of 1 show evidence for some interaction, although no such conclusion could be derived from the UV-visible absorption spectra. The results highlight the potential of phenyl beta-aminobisulfonates as building blocks for developing water-soluble pH and cation chemosensors.

Publication metadata

Author(s): Cardona MA, Kveder M, Baisch U, Probert MR, Magri DC

Publication type: Article

Publication status: Published

Journal: RSC Advances

Year: 2016

Volume: 6

Issue: 88

Pages: 84712-84721

Online publication date: 06/09/2016

Acceptance date: 27/08/2016

ISSN (electronic): 2046-2069

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/C6RA17791C

DOI: 10.1039/c6ra17791c

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