Synthesis and X-ray crystallographic studies of novel proton-ionizable nitro- and halogen-substituted acridono-18-crown-6 chromo- and fluorogenic ionophores |
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Authors: | Péter Huszthy Borbála VermesNikoletta Báthori Mátyás Czugler |
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Institution: | a Institute for Organic Chemistry, Budapest University of Technology and Economics, H-1521 Budapest, Hungary b Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1525 Budapest, Hungary |
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Abstract: | Starting from acridono-18-crown-6 ligand 1 (Fig. 1) seven new proton-ionizable chromogenic and fluorogenic ionophores 2-8 (Fig. 1) containing NO2 group(s) and/or Br or Cl atom(s) in the aromatic rings were prepared by electrophilic substitution. The precursor macrocycle 1 was obtained by a modification of the reported procedure which made chromatography unnecessary in purification and gave higher yield. X-ray crystallographic studies of the complexes of acridono-18-crown-6 type ligands 1, 2, 3, 6 and 8 show that the proton-ionizable units are in the acridone tautomeric form and that the ligands invariably bind a water molecule in their cavities by multipodal hydrogen bonding. In two cases (6 and 8) an additional DMF solvent molecule is also bound at the crown perimeter in the solid state. |
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Keywords: | acridones proton-ionizable crown ethers chromogenic ionophores fluorogenic ionophores multipodal hydrogen bonding X-ray crystallography |
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