期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 12, 页码 4797-4804出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo050324b
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Bis(calix[4]diquinones) 1 and 2 and double calix[4]diquinone 3 have been synthesized from their corresponding double calix [4] arenes 4, 5, and 6, respectively. Compounds 4-6 have been prepared from one-pot and stepwise syntheses under high pressure. Complexation studies of ligands 1-3 with alkali metal ions such as Li+, Na+, K+, and Cs+ were carried out by H-1 NMR titrations. Receptors 1 can selectively form 1:1 complexes with Na+. Ligand 2 prefers to form 1:1 complexes with K+ and Cs+. Receptor 3 retained the cone conformation of the calix [4] arene unit upon binding K+ but changed the conformation when complexing Li+ and Na+. Electrochemical studies using cyclic voltammetry and square wave voltammetry showed significant changing of voltammograms of 2 and 3 in the presence of alkali metal ions. Receptor 3 showed the electrochemically switched binding property toward Na+ and K+.
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