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
收稿日期: 2014-12-17
修回日期: 2015-02-06
网络出版日期: 2015-03-03
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
Received date: 2014-12-17
Revised date: 2015-02-06
Online 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).
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.
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 . DOI: 10.6023/cjoc201412031
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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