The synthesis of crown ether-appended dichlorofluoresceins and their selective Cu2+ chemosensing |
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| Authors: | Mi Hee Kim Jae Hyun Noh Sudeok Kim Sangdoo Ahn Suk-Kyu Chang |
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| Affiliation: | 1. Department of Physics, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia;2. Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia;3. Department of Physics, Firat University, 23169 Elazig, Turkey;4. Advances in Composites, Synthesis and Applications Group, King Abdulaziz University, Jeddah, Saudi Arabia;1. Faculdade de Ciências Agrárias e Veterinárias, UNESP/CPPAR, Via de acesso prof. Paulo Donatto Castellani, Jaboticabal, São Paulo, Brazil;2. Ouro Fino Agronegócios, Rodovia Anhanguera, Km 298, Cravinhos, São Paulo, Brazil. CEP: 14140-000 |
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| Abstract: | Dichlorofluorescein derivatives with two aza-crown ether binding units were prepared by the Mannich reaction and their chemosensing behaviors toward transition metal ions were investigated. An 18-crown-6 ether derivative exhibited pronounced Cu2+-selective fluorescence signaling, with selectivity over other common physiologically important alkali, alkaline earth and transition metal ions. The compound also displayed 1:1 complex formation with Cu2+ ion, with a detection limit of 2.9 × 10?6 M in an aqueous 50% DMSO solution at pH 7, showing that it may offer potential as a chemosensor for the detection of submillimolar Cu2+ ions in physiological environments. A 15-Crown-5 ether analogue also revealed selective Cu2+ signaling, although with somewhat diminished selectivity compared with its 18-crown-6 counterpart. |
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