Asymmetric calix[4]-thiacalix[4]arene tubes: Synthesis and ionophore properties

• Published in: Russian journal of organic chemistry Vol. 43; no. 2; pp. 192 - 200
• Main Authors: Khomich, E. V., Kashapov, M. N., Vatsuro, I. M., Shokova, E. A., Kovalev, B. B.
• Format: Journal Article
• Language: English
• Published: New York Springer Nature B.V 01-02-2007
• Subjects: Acetonitrile; Asymmetry; Complex formation; Iodides; NMR; Nuclear magnetic resonance; Organic chemistry; Potassium; Potassium carbonate; Rubidium; Tubes
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428007020078

Asymmetric p-tert-butylcalix[4]-p-R-thiacalix[4]arene tubes (R = tert-Bu, H, 1-adamantyl) were prepared for the first time by reaction of tosyloxyethoxy derivative of p-tert-butylcalix-[4]arene and the corresponding p-R-thiacalix[4]arenas in acetonitrile in the presence of K2CO3. Complex formation of compounds obtained with sodium, potassium, and rubidium iodides in CDCl3-CD3OD, 4:1, was studied by means of 1H NMR. The ionophore properties of the molecule were governed by the character of substituents on the upper rim of the thiacalixarene fragment, and only the molecular tube containing a fragment of the p-(1-adamantyl)-thiacalix[4]arene quantitatively bound potassium ions (quickly) and rubidium ions (slowly).