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

doi:10.6023/cjoc201511031

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1088-1093.DOI: 10.6023/cjoc201511031 Previous Articles Next Articles

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含硫脲基的多重氮杂杯[4]芳烃衍生物的合成与有机染料配合性能

严祯曦^a, 郭红玉^a, 杨发福^a,b, 袁锦^a

a. 福建师范大学化学与化工学院福州 350007;
b. 福建省高分子材料重点实验室福州 350007

收稿日期:2015-11-17 修回日期:2015-12-20 发布日期:2016-01-21
通讯作者: 杨发福 E-mail:yangfafu@fjnu.edu.cn
基金资助:
国家自然科学基金(No.21406036)、福建省自然科学基金(No.2014J01034)、福建省科技重点项目(No.2014N0025)和福建省高校科技创新团队支持计划(No.闽教科[2012]03号)资助项目.

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

Received:2015-11-17 Revised:2015-12-20 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).

1. Syntheses and Dyes Complexation Properties of Multiple-azo Calix[4]arene Derivatives Containing Thiourea Groups.PDF(1343KB)

Abstract

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

Cite this article

Yan Zhenxia, Guo Hongyua, Yang Fafu, Yuan Jin. Syntheses and Dyes Complexation Properties of Multiple-azo Calix[4]arene Derivatives Containing Thiourea Groups[J]. Chin. J. Org. Chem., 2016, 36(5): 1088-1093.

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含硫脲基的多重氮杂杯[4]芳烃衍生物的合成与有机染料配合性能

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

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