Chinese Journal of Organic Chemistry >
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).
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
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]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1514 -1519 . DOI: 10.6023/cjoc201412031
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