Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1863-1868.DOI: 10.6023/cjoc201602019 Previous Articles     Next Articles



林梁斌a, 郭红玉a, 杨发福a,b, 袁锦a   

  1. a 福建师范大学化学与化工学院 福州 350007;
    b 福建省高分子材料重点实验室 福州 350007
  • 收稿日期:2016-02-21 修回日期:2016-03-23 发布日期:2016-04-20
  • 通讯作者: 杨发福
  • 基金资助:

    国家自然科学基金(No. 21406036)、福建省自然科学基金(No. 2014J01034)、福建省科技重点(No. 2014N0025)和福建省高校科技创新团队支持计划(闽教科[2012]03号)资助项目.

Novel Biscalix[4]arene with Large Conjugated Aromatic Bridges: Synthesis and Complexation Properties for Dyes

Lin Liangbina, Guo Hongyua, Yang Fafua,b, Yuan Jina   

  1. a College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007;
    b Fujian Key Laboratory of Polymer Materials, Fuzhou 350007
  • Received:2016-02-21 Revised:2016-03-23 Published:2016-04-20
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21406036), the Natural Science Foundation of Fujian Province (No. 2014J01034), the Science and Technology Key Project of Fujian Province (No. 2014N0025) and the Program for Innovative Research Team in Science and Technology in Fujian Province University (No. [2012]03).

By reacting calix[4]arene-1,3-bis-amino derivative 3 with pyromellitic dianhydride, 1,4,5,8-naphthalenetetracar- boxylic dianhydride and perylene-3,4,9,10-tetracarboxylic dianhydride, respectively, three novel biscalix[4]arene derivatives 4, 5 and 6 with large conjugated aromatic bridges were prepared in “2+2” mode in yields of 60%~70%. The liquid-liquid extraction experiments of compounds 4, 5 and 6 suggested that they possess excellent extraction abilities for orange I (OI) and victoria blue B (VB). The extraction percentage of compound 6 for OI is as high as 88.3%. The complexation titration UV-vis spectra, Job plot titration and the ESI-MS complexation spectrum implied the formation of 1:1 complexes in DMSO solution. The highest association constant is 2.80×105 L·mol-1 for compound 6 with OI. The complexation abilities of compounds 4, 5 and 6 exhibit the order of compound 4< compound 5< compound 6, indicating that the aromatic conjugate bridges in biscalix[4]arene play important role for the dye complexation.

Key words: calix[4]arene, perylene, synthesis, dye, complexation