Novel Calixarene Benzo-15-crown-5 Derivatives: Synthesis and Complexation for Dyes

被引:3
|
作者
Yang, Fafu [1 ,2 ]
Wu, Yamin [1 ]
Ye, Jinqi [1 ]
Guo, Hongyu [1 ]
Yan, Xiaoyun [3 ]
机构
[1] Fujian Normal Univ, Coll Chem & Chem Engn, Fuzhou 350007, Peoples R China
[2] Fujian Key Lab Polymer Mat, Fuzhou 350007, Peoples R China
[3] Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
来源
JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY | 2014年 / 51卷 / 03期
基金
中国国家自然科学基金;
关键词
Calix[4]arene; benzo-15-crown-5; synthesis; complexation; dye; AQUEOUS-SOLUTIONS; AZO DYES; ADSORPTION; REMOVAL; RECEPTORS;
D O I
10.1080/10601325.2014.871952
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Three novel calix[4]arene, thiacalix[4]arene and calix[6]arene crown ether derivatives 6, 7 and 8 with integral crown ether rings were designed and synthesized in ideal yields by multiple procedures. The liquid-liquid extraction experiment showed that they possessed excellent extraction abilities towards three cationic and one anionic dyes [Orange I (OI), Methylene blue (MB), Neutral red (NR), Brilliant green (BG)]. The highest extraction percentage of compound 8 for Neutral red was 88.2%. Their complexation UV-Vis spectra with four dyes indicated 1:1 complexes between host and guest in DMSO solution. The complexation results and IR spectra suggested the crown ether ring, the bridging functional groups, and the cavity of calixarene unit participated in the complexation for dyes. The larger calixarene cavity was favorable for binding dyes. The association constant of compound 8 with BG was as high as 6.4x10(5) M-1.
引用
收藏
页码:223 / 228
页数:6
相关论文
共 50 条
  • [1] Synthesis of novel aminophosphonic derivatives of benzo-15-crown-5 ether
    Boduszek, B
    Luboch, E
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (12) : 2527 - 2531
  • [2] Complexation of tetrafluoroboric acid with benzo-15-crown-5
    V. I. Zhilov
    G. V. Kostikova
    L. G. Kuz´mina
    L. I. Demina
    S. V. Demin
    A. Yu. Tsivadze
    Russian Chemical Bulletin, 2018, 67 : 2191 - 2194
  • [3] Complexation of tetrafluoroboric acid with benzo-15-crown-5
    Zhilov, V. I.
    Kostikova, G. V.
    Kuz'mina, L. G.
    Demina, L. I.
    Demin, S. V.
    Tsivadze, A. Yu.
    RUSSIAN CHEMICAL BULLETIN, 2018, 67 (12) : 2191 - 2194
  • [4] COMPLEXATION OF LANTHANIDES WITH BENZO-15-CROWN-5 IN NONAQUEOUS SOLUTIONS
    STOUT, BE
    BUNZLI, JCG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 62 - INOR
  • [5] Synthesis of quinazoline derivatives containing veratrole and benzo-15-crown-5 moieties
    Saifullina N.Zh.
    Ibragimzhanov K.A.
    Tashmukhamedova A.K.
    Shakhidoyatov Kh.M.
    Chemistry of Heterocyclic Compounds, 1999, 35 (7) : 821 - 824
  • [6] NOVEL COMPLEXES OF CALCIUM WITH BENZO-15-CROWN-5
    POONIA, NS
    BHAGWAT, VW
    SARAD, SK
    INORGANIC & NUCLEAR CHEMISTRY LETTERS, 1977, 13 (5-6): : 227 - 230
  • [7] Synthesis of thiosemicarbazone derivatives of benzo-15-crown-5 and their anion recognition properties
    Zhou, Yan-Qing
    Wei, Tai-Bao
    Zhang, You-Ming
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (06) : 1478 - 1488
  • [8] Novel Benzo-15-crown-5/C60 Dyads with Different Chains: Synthesis and Complexation Properties
    Hong, Biqiong
    Yang, Fafu
    Ye, Jinqi
    Guo, Hongyu
    Yan, Xiaoyun
    LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (01) : 2 - 5
  • [9] NOVEL COMPLEXES OF MAGNESIUM WITH BENZO-15-CROWN-5
    POONIA, NS
    YADAV, BP
    BHAGWAT, VW
    NAIK, V
    MANOHAR, H
    INORGANIC & NUCLEAR CHEMISTRY LETTERS, 1977, 13 (02): : 119 - 122
  • [10] Polymethine dyes containing (benzo-15-crown-5)thiazole moiety
    Kovtun, YP
    Shandura, NP
    Tolmachev, AI
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1996, (07): : 992 - 996