Adamantane, the Building Block in the Construction of Macrocyclic Systems

Abstract

Dio naših istraživanja obuhvaća sintezu novih makrocikličkih polietera i politialaktona koji sadrže policikličke molekule ugrađene u makrociklički prsten ili vezane kao supstituent pokrajnjeg lanca. Pripravili smo niz oksa-, aza- i tiakrunastih etera s adamantanskom molekulom ugrađenom u makrociklički prsten i istraživali smo njihovu sposobnost kompleksiranja s metalnim kationima pomoću eksperimenata ekstrakcije pikratnih soli alkalijskih metala ili uporabom spektrometrije masa, metodom ionizacije elektroraspršenjem. Našli smo da vrsta heteroatoma kao i prisutnost adamantanske podjedinice utječe na selektivnost kompleksiranja metalnih iona, a također i na ukupnu lipofilnost makrocikličkog liganda.Part of our investigation was directed to the synthesis of novel macrocyclic polyethers, which contain polycyclic cage molecule, incorporated into the macrocyclic framework or attached as a side chain. We have prepared a series of adamantane-functionalized oxa-, aza- and thia-crown ethers, and studied their complexation abilities by alkali or transition metal picrate extraction experiments or by electrospray ionization mass spectrometry. In the homogeneous methanol/chloroform solutions as well as, in the extractions of metals from aqueous solution by macrocycles in chloroform, it was found that the type of heteroatom (O, N, S) and presence the adamantanesubstituents, influence the metal selectivity as well as the overall lipophilicity of the macrocyclic ligand

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