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Influence of structure rigidity on anion binding of bisureanaphthalene derivatives

Due to the involvement of anions in almost every biochemical process it is important to synthesize novel anion sensors with desired anion selectivity [1]. Many groups work on the design and synthesis of novel receptors characterized by better selectivity for anion complexation. Questions that still remain unanswered are mainly related to the geometry of the receptors, such as influence of molecular rigidity, or number of necessary binding sites for the desired selectivity. Recently we reported some examples of anion complexation by adamantyl dipyrromethane derivatives wherein recognition was influenced by molecular rigidity [2]. In search for receptors that would offer selectivity to biologically important oxo-anions such as phosphate, we focused our attention to urea derivatives [3]. Herein we report on anion binding ability of a series of bisureanaphthalene derivatives. The series is prepared in order to investigate the influence of structure rigidity to the binding selectivity. Therefore the anion binding of adamantyl bisurea derivatives was compared to the analogous host molecules wherein the urea moieties are separated by flexible alkyl linkers of the same length, and adamantane monourea derivative. The complexation was investigated by UV-vis, fluorescence and NMR spectroscopy [4].

anion binding; urea; naphthalene derivatives

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