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

Cardona, Maria; Kveder, Marina; Baisch, Ulrich; Probert, Michael; Magri, David (2016) Water-soluble beta-aminobisulfonate building blocks for pH and Cu2+ indicators. RSC Advances, 6 . pp. 84712-84721. ISSN 2046-2069

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Two water-soluble phenyl beta-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 beta-aminobisulfonate 1 and methoxyphenyl beta- 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.

Item Type: Article
Additional Information: We acknowledge financial support from the University of Malta, the Strategic Educational Pathways Scholarship (Malta) part financed by the European Social Fund (ESF) under Operational Programme II, and European Cooperation in Science and Technology (COST Action CM1005 "Supramolecular Chemistry in Water"). We extend our gratitude to Prof. Robert M. Borg at the University of Malta, and Dr. Damjan Makuc and Prof. Janez Plavec at the Slovenian NMR Centre in Ljubljana for assistance with 1H NMR experiments. The authors thank the Diamond Light Source for access to beamline I19.
Uncontrolled Keywords: chemosensors; aminobisulfonate
Subjects: NATURAL SCIENCES > Physics
NATURAL SCIENCES > Chemistry > Analytic Chemistry
Divisions: Division of Physical Chemistry
Project titleProject leaderProject codeProject type
Molekulska struktura i dinamika sustava s paramagnetskim česticama-Marina Ilakovac-Kveder098-0982915-2939MZOS
Depositing User: Marina Ilakovac Kveder
Date Deposited: 15 Apr 2019 07:39
DOI: 10.1039/c6ra17791c

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