A novel host molecule p-[1-(4-hydroxyphenyl)-1-methylethyl]calix[8]arene. Synthesis and complexation properties in non-aqueous polar solution

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Chen-Ho Tung and Hai-Feng Ji


Abstract

A novel deep-cavity calixarene, p-[1-(4-hydroxyphenyl)-1-methylethyl]calix[8]arene 1 was synthesized and its complexation with aromatic compounds was examined. Reaction of p-[1-(4-methoxyphenyl)-1-methylethyl]phenol 2 with paraformaldehyde under various conditions only resulted in p-[1-(4-methoxyphenyl)-1-methylethyl]calix[8]arene 3, and no corresponding calix[4]arene and calix[6]arene were detected. Removal of the methyl in the ether groups of 3 afforded 1 in 80% yield. Solubilization, fluorescence and photochemical probe studies demonstrated that 1 forms inclusion complexes with a variety of aromatic compounds in polar non-aqueous solutions.


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