Chinese Journal of Organic Chemistry >
Syntheses and Dyes Complexation Properties of Multiple-azo Calix[4]arene Derivatives Containing Thiourea Groups
Received date: 2015-11-17
Revised date: 2015-12-20
Online published: 2016-01-21
Supported by
Project supported by the National Natural Science Foundation of China (No. 21406036), the Natural Science Foundation of Fujian Province (No. 2014J01034), the Fujian Province Science and Technology Key Project (No. 2014N0025) and the Program for Innovative Research Team in Science and Technology in Fujian Province University (No. [2012]03).
By using calix[4]arene as platform, the construction of calix[4]arene derivatives with unique structures and binding properties is the important research field in organic supramolecular chemistry. In this paper, the chain-opening calix[4]arene bi-thiourea derivative 4 was synthesized by reacting calix[4]arene bi-aromatic amino derivative 3 with phenyl isothiocyanate in yield of 95%. Treating compound 3 with p-phenylene diisothiocyanate (molar ratio=1:1) gave bridging calix[4]arene bi-thiourea derivative 5 in yield of 80%. Treating compound 3 with excess p-phenylene diisothiocyanate afforded calix[4]arene thiourea derivative 6 in yield of 82%and was further converted to multiple-azo calix[4]arene derivative 7 by reacting compound 6 with salicylyl hydrazine in yield of 75%. The experiments of UV titration spectra for four tested dyes (orange I, alizarin green, victorial blue and methylene blue) showed that compounds 4~7 possessed excellent complexation abilities with 1:1 ratios for complexation and 105 magnitudes for the association constants. The chain-opening structure, more amino groups and more aromatic groups were favorable for the improvement of complexation abilities.
Key words： calix[4]arene; thiourea; synthesis; dye; complexation
Yan Zhenxia , Guo Hongyua , Yang Fafu , Yuan Jin . Syntheses and Dyes Complexation Properties of Multiple-azo Calix[4]arene Derivatives Containing Thiourea Groups[J]. Chinese Journal of Organic Chemistry, 2016 , 36(5) : 1088 -1093 . DOI: 10.6023/cjoc201511031
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