Chinese Journal of Organic Chemistry >
Synthesis and Dyes Complexation of Calix[4]arene Derivatives with Azo-macrocyclic Cavities
Received date: 2013-08-21
Revised date: 2013-10-07
Online published: 2013-10-11
Supported by
Project supported by the Program for Innovative Research Team in Science and Technology in Fujian Province University (No. [2012]03), the Program for Excellent Young Researchers in University of Fujian Province (No. JA10056), and the Project of Fujian Provincial Department of Education (No. JA11044).
Calix[4]arene hydrazide derivative 4 was obtained by reacting calix[4]-1,3-bis-ester derivative 3 with hydrazine. Then reacting compound 4 with hexamethylene diisocyanate or long aliphatic bis-aldehyde derivative 2 in “1+1” condensation mode, two novel calix[4]arene derivatives 5 and 6 with azo-macrocyclic cavity were obtained in yields of 85% and 80%, respectively. The liquid-liquid two phase extraction experiments showed that the extraction percentages of compounds 5 and 6 for orange I and methylene blue were more than 80%. The experiments of UV titration spectra suggested that they exhibited good complexation abilities for dyes with 1:1 ratios for complexation and 104 magnitudes for the association constants.
Key words： calix[4]arene; azo-macrocyclic; synthesis; dye; complexation
Hong Biqiong , Yang Fafu , Guo Hongyu , Liu Zhiqiang . Synthesis and Dyes Complexation of Calix[4]arene Derivatives with Azo-macrocyclic Cavities[J]. Chinese Journal of Organic Chemistry, 2014 , 34(2) : 424 -428 . DOI: 10.6023/cjoc201308028
[1] Sliwa, W.; Kozlowski, C. Calixarenes and Resorcinarenes, Wiley-VCH, Weinheim, 2009.
[2] Joseph, R.; Rao C. P. Chem. Rev. 2011, 111, 4658.
[3] Zhang, Y.; Yang, F.; Bai, X.; Liu, Z.; Guo, H. Chin. J. Org. Chem. 2012, 32, 2350 (in Chinese).
(张瑛美, 杨发福, 白小艳, 刘志强, 郭红玉, 有机化学, 2012, 32, 2350.)
[4] Ye, J.; Yang, F.; Zhang, X.; Jiao, Z.; Guo, H. Chin. J. Org. Chem. 2012, 32, 189 (in Chinese).
(叶进启, 杨发福, 张筱逸, 焦自玉, 郭红玉, 有机化学, 2012, 32, 189.)
[5] Xu, B.; Yang, F.; Liu, Z.; Chai, X.; Guo, H. Chin. J. Org. Chem. 2011, 31, 737 (in Chinese).
(许冰婷, 杨发福, 刘志强, 柴先锋, 郭红玉, 有机化学, 2011, 31, 737.)
[6] Yang, F.; Wang, Y.; Guo, H.; Xie, J.; Liu, Z. Can. J. Chem. 2010, 88, 622.
[7] Yang, F.; Huang, Z.; Guo. Y.; Hong, B.; Zhang, X. J. Inclusion Phenom. Macrocyclic Chem. 2011, 70, 11.
[8] Yang, F.; Jiao, Z.; Huang, Z.; Xie, J.; Guo, H. J. Inclusion Phenom. Macrocyclic Chem. 2012, 74, 257.
[9] Sang, Q.; Yan, J. Chin. J. Chem. 2012, 30, 1410.
[10] Wong, Y.; Yu, J. Water Res. 1999, 33, 3512.
[11] Crini, G. Prog. Polym. Sci. 2005, 30, 38.
[12] Akceylan, E.; Bahadir, M.; Yilmaz, M. J. Hazard. Mater. 1999, 162, 960.
[13] Yilmaz, E. O.; Sirit, A.; Yilmaz, M. J. Macromol. Sci., Part A: Pure Appl. Chem. 2007, 44, 167.
[14] Yilmaz, A.; Yilmaz, E.; Yilmaz, M. Dyes Pigm. 2007, 74, 54.
[15] Kamboh, M.; Solangi, I.; Sherazi, S. Desalination 2011, 268, 83.
[16] Kamboh, M.; Solangi, I.; Memon, S. J. Hazard. Mater. 2011, 186, 651.
[17] Bai, X.; Yang, F.; Xie, J.; Guo, H. J. Macromol. Sci., Part A: Pure Appl. Chem. 2013, 50, 334.
[18] Yang, F.; Liu, W.; Xie, J.; Bai, X.; Guo, H. J. Inclusion Phenom. Macrocyclic Chem. 2013, 76, 311.
[19] Connors, K. Binding Constants, Wiley, New York, 1987.
[20] Yang, F.; Zheng, L.; Ji, Y.; Guo, H.; Lin, J. Chin. J. Org. Chem. 2006, 26, 268 (in Chinese).
(杨发福, 郑林禄, 季衍卿, 郭红玉, 林建荣, 有机化学, 2006, 26, 268.)
/
| 〈 |
|
〉 |
