Abstract
The synthesis of two new 9-phenylacridino-18-crown-6 ether type sensor molecules [1 and (R,R)-2] was accomplished. The cation recognition ability of the achiral sensor molecule 1 towards various ions was studied in acetonitrile by UV/Vis and fluorescence spectroscopies. Our studies revealed the binding of Ag+, Cd2+, Ni2+, Pb2+, Zn2+ and NH4+ ions by the latter molecule. Selectivity of the chiral dimethyl-substituted analogue (R,R)-2 was studied toward the enantiomers of the hydrogen perchlorate salts of 1-phenylethylamine, 1-(1-naphthyl)ethylamine, phenylglycine methyl ester and phenylalanine methyl ester using fluorescence spectroscopy.
Highlights
Since Pedersen reported the preparation and studies of the first crown ethers [1, 2] these host molecules have gained much attention [3, 4]
The selectivity of crown ethers is based on a generally occurring vital phenomenon called molecular recognition, which is governed by non-covalent intermolecular forces, such as hydrogen bonding, π–π interaction [5, 6] and cation–π interaction [7, 8], taking place between host and guest molecules
The enantioselective complexing ability of chiral macrocycles is based on enantiomeric recognition, which is a special case of molecular recognition involving the discrimination between the enantiomers of a chiral guest molecule by a chiral host molecule
Summary
Since Pedersen reported the preparation and studies of the first crown ethers [1, 2] these host molecules have gained much attention [3, 4]. The enantioselective complexing ability of chiral macrocycles is based on enantiomeric recognition, which is a special case of molecular recognition involving the discrimination between the enantiomers of a chiral guest molecule by a chiral host molecule. The discriminating ability of crown ether-based sensor molecules, toward various cations and the enantiomers of chiral compounds, has been studied by UV/ Vis and fluorescence spectroscopies [9,10,11,12,13,14,15,16,17]. Several optically active macrocycles have been used as enantioselective selector molecules in transport studies [18], in capillary electrophoresis [19] and in liquid chromatography [20,21,22,23,24,25]
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