Synthesis and Properties of Novel Azocalix[4]arene Derivatives with Azo and Imino Groups as the Lower Margin Chelating Arm

doi:10.6023/cjoc201412031

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1514-1519.DOI: 10.6023/cjoc201412031 Previous Articles Next Articles

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偶氮和亚氨基团作为下垂螯合臂的新型杯[4]芳烃衍生物的合成及性质

范平, 徐生明, 李巍巍, 陈辰, 祃艳强

辽宁大学化学院沈阳 110036

收稿日期:2014-12-17 修回日期:2015-02-06 发布日期:2015-03-03
通讯作者: 范平 E-mail:pingfan_bft@126.com
基金资助:
辽宁省教育局科学研究基金(No. L2011007)和沈阳市科技局科技计划(No. F13-318-1-51)资助项目.

Synthesis and Properties of Novel Azocalix[4]arene Derivatives with Azo and Imino Groups as the Lower Margin Chelating Arm

Fan Ping, Xu Shengming, Li Weiwei, Chen Chen, Ma Yanqiang

Institute of Chemistry, Liaoning University, Shenyang 11003

Received:2014-12-17 Revised:2015-02-06 Published:2015-03-03
Supported by:
Project supported by the Liaoning Provincial Department of Education Fund for Scientific Research (No. L2011007) and the Shenyang Science and Technology Bureau of Science and Technology Program (No. F13-318-1-51).

1. Synthesis and Properties of Novel Azocalix[4]arene Derivatives with Azo and Imino Groups as the Lower Margin Chelating Arm.PDF(650KB)

Abstract

A serious of calix[4]arene derivatives containing azo and imino group in the lower rim were synthesized by substitution and condensation reactions from p-tert-butylcalix[4]arene. The structures of products were characterized by IR, ¹H NMR, ¹³C NMR and elemental analysis. Their complexation behavior toward various metal ions was investigated by UV/vis spectroscopy. The results showed that 25,27-dihydroxy-26,28-bis{2-[2-(N-(4-phenylazo-1-naphthyl)iminomethyl)phenoxy]- ethoxy}-p-tert-butylcalix[4]arene (4c) could identify Al³⁺ and Sn²⁺, and 25,27-dihydroxy-26,28-bis{2-[2-(N-(4-(4- methylphenylazo)-1-naphthyl)iminomethyl)phenoxy]ethoxy}-p-tert-butylcalix[4]arene (4e) could identify Al³⁺ specifically. The stoichiometry of 4e to Al³⁺ in the complex was 1:1.

Key words: calyx[4]arene, azo group, imino group, UV/Vis spectroscopy

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Fan Ping, Xu Shengming, Li Weiwei, Chen Chen, Ma Yanqiang. Synthesis and Properties of Novel Azocalix[4]arene Derivatives with Azo and Imino Groups as the Lower Margin Chelating Arm[J]. Chin. J. Org. Chem., 2015, 35(7): 1514-1519.

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偶氮和亚氨基团作为下垂螯合臂的新型杯[4]芳烃衍生物的合成及性质

Synthesis and Properties of Novel Azocalix[4]arene Derivatives with Azo and Imino Groups as the Lower Margin Chelating Arm

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