Studies of electrochemically switchable anthraquinone crown ethers and podands and the syntheses of fluorescent probes

Date of Award




Degree Name

Doctor of Philosophy (Ph.D.)



First Committee Member

George W. Gokel - Committee Chair


In Part I, anthraquinone-derived macrocyclic polyether systems have been synthesized and their cation binding properties were studied. Several compounds have been utilized in active membrane transport by redox switching mechanism.Anthraquinone-derived crown ethers (21-23) and bibracchial podand (BiP) (33-36) systems exhibited cation (Li$\sp+$, Na$\sp+$, and K$\sp+$) binding enhancements upon reduction. While structurally rigid anthraquinone crown ethers, 21 and 22, exhibit an unusually high binding enhancement for Li$\sp+$, Na$\sp+$, and K$\sp+$, the flexible anthraquinone BiPs, 33 and 34 also showed strong ion-pair interaction. In syn- and anti-BiPs, each sidearm acts independently to coordinate one or two cations.The complexing ability of poly(ethyleneoxy) podand has been observed in the nucleophilic aromatic substitution reaction of anthraquinone-derived podands. Unsymmetrically substituted anthraquinone podands bearing a lipophilic moiety (73 and 75) have been synthesized by using leaving group ability of anthraquinone podands.In Part II, fluorescent probes to measure the cytosolic ion concentration have been prepared. The desired potassium probe was attained by the condensation of ionophore (diazacrown ether), fluorophore (benzofuran), and membrane permeable group (acetoxymethyl ester) which can be hydrolyzed to stay inside cell.


Chemistry, Organic

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