Citation: 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 shu

Syntheses and Dyes Complexation Properties of Multiple-azo Calix[4]arene Derivatives Containing Thiourea Groups

Yan Zhenxia ^a ,
Guo Hongyua ^a ,
Yang Fafu ^a,b,*,, ,
Yuan Jin ^a

a.
College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007
b.
Fujian Key Laboratory of Polymer Materials, Fuzhou 350007

Corresponding author: Yang Fafu, yangfafu@fjnu.edu.cn
Received Date: 17 November 2015
Revised Date: 20 December 2015

Fund Project: the Natural Science Foundation of Fujian Province No.2014J01034and the Program for Innovative Research Team in Science and Technology in Fujian Province University No. [2012]03the Fujian Province Science and Technology Key Project No.2014N0025Project supported by the National Natural Science Foundation of China No.21406036

Figures(3)

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.
- calix[4]arene,
- thiourea,
- synthesis,
- dye,
- complexation
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