
%0 Journal Article
%A Atkinson, Ian M. 
%A Boghai, Davar M. 
%A Lindoy, Leonard F. 
%A Ghanbari, Bahram 
%A Meehan, George V. 
%A Saini, Vinod 
%T New Macrocyclic Ligands. VIII Di- and Tri-linked Macrocyclic Systems Incorporating N<emph tye="8">2</emph>O<emph tye="8">2</emph>-Donor Atoms
%J Australian Journal of Chemistry
%D 1999/07/23
%V 52
%N 5
%P 351-358
%K 
%R https://doi.org/10.1071/CH99054
%U https://www.publish.csiro.au/paper/CH99054 
%X The synthesis and characterization of new lipophilic di- and tri-linked O2N2-donor macrocycles is reported. The synthesis of the dilinked species involved the initial alkylation of one secondary nitrogen of the parent 15-membered, O2N2-donor macrocycle (1) with 2-bromoethanol or with ethylene oxide to yield (2), followed by protection of the appended alcohol group by reaction with t-butyldiphenylsilyl chloride to give (3). Two such moieties were then bridged via a diacylation reaction with ClCO(CH2)8COCl to yield the corresponding diamide product (4). Deprotection of the alcohol functions followed by reduction of the both amide linkages resulted in formation of theN,N&#8242;-alkyl-linked species (5) incorporating two pendant hydroxyethyl groups. This product was then converted &#91;via the corresponding dichloro derivative (6)&#93; into the diether (7) by condensation with 4-t-butylphenol. By use of analogous chemistry, the trilinked trismacrocycle species (12), based on a phloroglucinol core, has also been synthesized. An aim of the present study was thus the preparation of new &#8216;linked&#8217; macrocyclic systems that might be expected to show higher lipophilicity than their corresponding single-ring systems. These were designed for future use as ionophores in metal ion membrane transport (and solvent extraction) experiments. 
