Excimer-Based On-Off Bis(pyreneamide) Macrocyclic Chemosensors
Mahesh Vishe
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorTimothée Lathion
Department of Inorganic and Analytical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorSimon Pascal
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorOleksandr Yushchenko
Department of Physical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorAlexandre Homberg
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorElodie Brun
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorEric Vauthey
Department of Physical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorClaude Piguet
Department of Inorganic and Analytical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorJérôme Lacour
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorMahesh Vishe
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorTimothée Lathion
Department of Inorganic and Analytical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorSimon Pascal
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorOleksandr Yushchenko
Department of Physical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorAlexandre Homberg
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorElodie Brun
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorEric Vauthey
Department of Physical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorClaude Piguet
Department of Inorganic and Analytical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorJérôme Lacour
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland
Search for more papers by this authorAbstract
A series of bis(pyreneamide) macrocycles, synthesized in two steps from THF, THP, oxepane and 1,4-dioxane, are tested as chemosensors for a large range of mono-, di- and trivalent cations. In their native states, these macrocycles exhibit a strong excimer fluorescence that is quenched upon the addition of the metal ions (alkaline, alkaline earth, p-, d-, and f-block metals). UV-Vis spectrophotometric titrations, cyclic voltammetry, excimer fluorescence quenching, and transient absorption spectroscopy experiments helped characterize the On-Off changes occurring upon binding and demonstrate that the highest stability constants are obtained with divalent cations Ca2+ and Ba2+ specifically.
Supporting Information
Supporting information for this article is available on the WWW under https://doi.org/10.1002/hlca.201700265.
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