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

doi:10.6023/cjoc201412031

有机化学 ›› 2015, Vol. 35 ›› Issue (7): 1514-1519.DOI: 10.6023/cjoc201412031 上一篇下一篇

研究论文

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).

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1. 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.PDF(650KB)

摘要/Abstract

以对叔丁基杯[4]芳烃为原料, 经过取代、缩合等多步反应, 合成了5个下缘同时含有偶氮和亚氨基团的新型杯[4]芳烃衍生物, 其结构经IR、¹H NMR、¹³C NMR和元素分析进行了表征. 并通过UV/Vis光谱研究了其对金属离子的识别作用. 结果发现化合物25,27-二羟基-26,28-二{2-[2-(N-(4-苯偶氮基-1-萘基)亚氨基次甲基)苯氧基]乙氧基}对叔丁基杯[4]芳烃(4c)对Al³⁺和Sn²⁺有较好的识别作用, 而化合物25,27-二羟基-26,28-二{2-[2-(N-(4-(4-甲基苯偶氮基)-1-萘基)亚氨基次甲基)苯氧基]乙氧基}对叔丁基杯[4]芳烃(4e)可以专一性地识别Al³⁺, 其与Al³⁺络合的物质的量比为1:1.

关键词: 杯[4]芳烃, 偶氮基团, 亚氨基团, UV/Vis光谱

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

引用此文

范平, 徐生明, 李巍巍, 陈辰, 祃艳强. 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[J]. 有机化学, 2015, 35(7): 1514-1519.

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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