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Water-soluble β-aminobisulfonate building blocks for pH and Cu 2+ indicators

DOI: 10.1039/C6RA17791C DOI Help

Authors: Maria A. Cardona (University of Malta) , Marina Kveder (Rudjer Boskovic Institute) , Ulrich Baisch (University of Newcastle Upon Tyne) , Mike Probert (Newcastle University) , David C. Magri (University of Malta)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Rsc Adv. , VOL 6 , PAGES 84712 - 84721

State: Published (Approved)
Published: September 2016
Diamond Proposal Number(s): 6749

Abstract: Two water-soluble phenyl β-aminobisulfonate ligands were synthesised and characterised by spectroscopic techniques including UV-visible absorption, electron paramagnetic resonance (EPR) and 1H 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 pKas of the phenyl β-aminobisulfonate 1 and methoxyphenyl β-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 β-aminobisulfonates as building blocks for developing water-soluble pH and cation chemosensors.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

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