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Synthesis and optical characterization of novel enantiopure BODIPY linked azacrown ethers as potential fluorescent chemosensors |
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| Authors: | Ildikó Móczár Zita Maidics Klára Tóth |
| Institution: | a Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, PO Box 91, H-1521 Budapest, Hungary b Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, H-1521 Budapest, Hungary c Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, PO Box 91, H-1521 Budapest, Hungary d Research Group of Technical Analytical Chemistry of the Hungarian Academy of Sciences, PO Box 91, H-1521 Budapest, Hungary e Chinoin Pharmaceutical and Chemical Works Ltd., PO Box 110, H-1325 Budapest, Hungary |
| Abstract: | Two novel enantiopure BODIPY linked azacrown ether chemosensors were prepared by reacting 3-chloro-5-methoxyBODIPY with new enantiopure monoaza-18-crown-6 ether ligands bearing two methyl and isobutyl groups on their chiral centres, respectively. The latter compounds were synthesized starting from optically active tetraethylene glycols in six steps. The operation of chemosensors is based on the intramolecular charge transfer (ICT) process. They exhibit pronounced off-on type fluorescent responses to some metal ions and chiral primary aralkyl ammonium ions, in particular to Ca2+ and Pb2+. Even in the case of 1:1 ratio of Ca2+ and Pb2+ ions to the ionophores, the fluorescence intensities and quantum yield values increased more than 10-fold, as well as both the absorption and emission bands were blue-shifted by about 20-30 nm (hipsochromic effect) in acetonitrile. The formation of relatively stable complexes allowed the determination of log Ks values by the mole-ratio method. |
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