engleski

SYNTHESIS AND BINDING PROPERTIES OF NOVEL ADAMANTANE FUNCTIONALIZED DIAZA-BIBRACCHIAL LARIAT ETHERS

Since Pedersen discovered crown ethers as a new class of compounds with unusual powerful non-covalent cation binding properties, they have played an important role in a number of areas in chemistry, the most notable being their application as synthetic receptors for organic and inorganic cations, anions and neutral molecules.[1] Many different modifications of the crown ethers, such as changing the ring size, the kind of substituents, and the type of donor atoms, have been made to enhance their complexation properties. In recent years there is a number of papers describing the crown ethers which contain polycyclic moiety.[2] Incorporation of a rigid polycyclic molecule such as cubane, pentacycloundecane or adamantane into crown ethers should affect their conformational mobility and complexation abilities. The lipophilic polycyclic moiety should increase the solubility of the crown ethers in nonpolar media and thereby increase their ability for ion transport via their complexation with metal ions. We describe the synthesis of four novel, highly lipophilic diaza-18-crown-6 ethers with adamantane moieties attached to side arms as well as investigation of their binding abilities towards alkali metal cations and their transport abilities through liquid membrane.

adamantane; diaza-18-crown-6 ethers; binding and transport abilities

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