Acridino-Diaza-20-Crown-6 Ethers: New Macrocyclic Hosts for Optochemical Metal Ion Sensing |
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| Authors: | dm Golcs Korinna Kovcs Panna Vezse Tünde Tth Pter Huszthy |
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| Institution: | 1.Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., H-1111 Budapest, Hungary; (K.K.); (P.V.); (T.T.); (P.H.);2.Institute for Energy Security and Environmental Safety, Centre for Energy Research, Konkoly-Thege Miklós út 29-33., H-1121 Budapest, Hungary |
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| Abstract: | Acridino-diaza-20-crown-6 ether derivatives as new turn-on type fluorescent chemosensors with an excellent functionality and photophysical properties have been designed and synthesized for metal ion-selective optochemical sensing applications. Spectroscopic studies revealed that in an acetonitrile-based semi-aqueous medium, the sensor molecules exhibited a remarkable fluorescence enhancement with high sensitivity only toward Zn2+, Al3+ and Bi3+, among 23 different metal ions. Studies on complexation showed a great coordinating ability of logK > 4.7 with a 1:1 complex stoichiometry in each case. The detection limits were found to be from 59 nM to micromoles. The new ionophores enabled an optical response without being affected either by the pH in the range of 5.5–7.5, or the presence of various anions or competing metal ions. Varying the N-substituents of the new host-backbone provides diverse opportunities in both immobilization and practical applications without influencing the molecular recognition abilities. |
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| Keywords: | acridine macrocycles metal ion complexation fluorescence optochemical sensor |
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