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Proceedings

Fluorescent Calix[4]arene-Oxacyclophane Sensor for Transition Metal Cations

1
Departamento de Engenharia Química, Instituto Superior de Engenharia de Lisboa, Instituto Politécnico de Lisboa, R. Conselheiro Emídio Navarro, 1, 1959-007 Lisboa, Portugal
2
Centro de Química-Vila Real, Universidade de Trás-os-Montes e Alto Douro, 5001-801 Vila Real, Portugal
*
Author to whom correspondence should be addressed.
Presented at the 24th International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2020; Available online: https://ecsoc-24.sciforum.net/.
Published: 16 November 2020
The sensing behavior of a calix[4]arene-oxacyclophane-carbazole conjugate (1) towards Cu(I) ions was investigated. Contrary to the noteworthy sensitivity and selectivity previously found for Cu(II), the affinity of 1 for Cu(I) cations is much lower. Through fluorescence titration assays, the apparent binding constants (Ka) for the two ions were determined, showing that an affinity of over thirteen fold was displayed for Cu(II). Two Cu(I) counter-ions were used to determine possible effects on the binding event. It was found that acetate and iodide ions behave similarly, yielding Ka of the same magnitude. Formation of a ground-state supramolecular complex between 1 and Cu(I) ions was not observed on UV-Vis titrations, in contrast to what was previously reported for Cu(II) using the same host. The affinity of 1 for Fe(III), a major biological competitor, was also assessed. The fluorescence of host 1 is quenched by Fe(III) ions although to a lesser extent (32% less efficient than Cu(II)). The study demonstrates that calixarene 1 is able to differentiate copper ions in two common oxidation states using fluorescence techniques, thereby suggesting its application for redox-active centers in biomimetic chemistry.
Keywords: calix[4]arene; copper(I); copper(II); iron(III); supramolecular; inclusion complex; fluorescence; sensor calix[4]arene; copper(I); copper(II); iron(III); supramolecular; inclusion complex; fluorescence; sensor
MDPI and ACS Style

Costa, A.I.; Barata, P.D.; Prata, J.V. Fluorescent Calix[4]arene-Oxacyclophane Sensor for Transition Metal Cations. Chem. Proc. 2021, 3, 40. https://0-doi-org.brum.beds.ac.uk/10.3390/ecsoc-24-08453

AMA Style

Costa AI, Barata PD, Prata JV. Fluorescent Calix[4]arene-Oxacyclophane Sensor for Transition Metal Cations. Chemistry Proceedings. 2021; 3(1):40. https://0-doi-org.brum.beds.ac.uk/10.3390/ecsoc-24-08453

Chicago/Turabian Style

Costa, Alexandra I., Patrícia D. Barata, and José V. Prata 2021. "Fluorescent Calix[4]arene-Oxacyclophane Sensor for Transition Metal Cations" Chemistry Proceedings 3, no. 1: 40. https://0-doi-org.brum.beds.ac.uk/10.3390/ecsoc-24-08453

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