Abstract
New highly lipophilic enantiopure crown ethers containing a heterocyclic unit have been synthesized. Phase transport, UV-Vis- and fluorescence spectrophotometric investigations as well as electrochemical studies on the complexation of the new macrocycles with several amine and amino acid derivatives were also carried out. Achiral amines were used for studying the structural preference of the new macrocycles. Among the studied structural features of the guest molecules, the intermolecular π-π interaction showed the most significant effect on complexation, which made the aralkylamine-type compounds the most preferable guest molecules. The studied liquid membrane-based applications and photophysical investigations showed appreciable enantiomeric recognition toward some aralkylamine model compounds with homochiral preferences. New crown ether derivatives (R,R)-2 and (S,S)-2 were successfully applied as enantioselective carrier and sensor molecules.
Highlights
The synthesis of chiral macrocycles possessing an enantiomeric recognition ability has been the focus of interest since the beginning of supramolecular chemical research
Intypically long alkyl chains are incorporated into the polyether ring of the macrocycles this paper, we describe the synthesis and characterization of new highly lipophilic
We reported the synthesis and characterization of new enantiopure highly lipophilic acridonoand acridino-crown ether derivatives, including the synthetic difficulties encountered during the preparation of the new compounds
Summary
The synthesis of chiral macrocycles possessing an enantiomeric recognition ability has been the focus of interest since the beginning of supramolecular chemical research. A few years later, chiral macrocycles capable of discriminating between the enantiomers of amine derivatives were reported [2,3]. Numerous publications have focused on the supramolecular interaction-based stereoselective differentiation of amine compounds by chiral macrocyclic hosts, which has resulted in a number of applications using them as sensor [4,5,6,7,8,9,10], selector [11,12] and transporter [13] molecules. It was found that the conformational rigidity of the host molecule increases the degree of enantiomeric recognition. The conformational rigidity of the macrocycles usually can be attained by Molecules 2020, 25, 2571; doi:10.3390/molecules25112571 www.mdpi.com/journal/molecules
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