Utilizing a pH‐Sensitive Dye in the Selective Fluorescent Recognition of Sulfate |
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| Authors: | Aleksandr M. Agafontsev Tatiana A. Shumilova Dr. Pavel A. Panchenko Sharon Janz Prof. Olga A. Fedorova Evgeny A. Kataev |
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| Affiliation: | 1. Institute of Chemistry, Technische Universit?t Chemnitz, Chemnitz, Germany), Fax: +49 (0) 371 531 839841;2. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia;3. A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Moscow, Russia;4. D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Russia |
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| Abstract: | A receptor containing amidopyrrole binding subunits and free amino groups, conjugated to a naphthalimide dye, has been designed and synthesized. The intrinsic selectivity of the binding motif for phosphate present in DMSO completely disappears in 10 % DMSO aqueous buffer at pH 3.6, at which the receptor is protonated. The electrostatic interactions between the receptor and an anion start to dominate, thus leading to selectivity for sulfate. The ability of the HSO4? anion to transfer the proton to the amino group during the recognition event suppresses the photoinduced electron transfer (PET) on the dye, resulting in a selective turn‐on fluorescent response. The choice of pH of the solution for sensing is dictated by the pKa value of the dye. |
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| Keywords: | anions fluorescent probes molecular recognition naphthalimide supramolecular chemistry |
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