- Excimer-Based On-Off Bis(pyreneamide) Macrocyclic Chemosensors
Mahesh Vishe, Timothée Lathion, Simon Pascal, Oleksandr Yushchenko, Alexandre Homberg, Elodie Brun, Eric Vauthey, Claude Piguet, Jérôme Lacour
Helv. Chim. Acta 2018, 101, e1700265
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.
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