Citation: Lin Liangbin, Guo Hongyu, Yang Fafu, Yuan Jin. Novel Biscalix[4]arene with Large Conjugated Aromatic Bridges: Synthesis and Complexation Properties for Dyes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1863-1868. doi: 10.6023/cjoc201602019 shu

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

Lin Liangbin ^a ,
Guo Hongyu ^a ,
Yang Fafu ^a,b,*,, ,
Yuan Jin ^a

a.
College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007
b.
Fujian Key Laboratory of Polymer Materials, Fuzhou 350007

Corresponding author: Yang Fafu, yangfafu@fjnu.edu.cn
Received Date: 21 February 2016
Revised Date: 23 March 2016

Fund Project: the Natural Science Foundation of Fujian Province No. 2014J01034Project supported by the National Natural Science Foundation of China No. 21406036the 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

Figures(6)

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.
- calix[4]arene,
- perylene,
- synthesis,
- dye,
- complexation
1. [1]
  Wong, Y.; Yu, J. Water Res. 1999, 33, 3512.
2. [2]
  Parker, H. L.; Hunt, A. J.; Budarin, V. L.; Shuttleworth, P. S.; Miller, K. L.; Clark, J. H. RSC Adv. 2012, 2, 8992.
3. [3]
  Guo Y. L.; Hou W. G.; Liang J. L.; Liu J. Q.; Rinaudo M. Chem. Res. Chin. Univ. 2014, 30, 837.
4. [4]
  Apostol, L. C.; Pereira, L.; Pereira, R.; Gavrilescu, M.; Alves, M. M. Biodegradation 2012, 23, 725.
5. [5]
  Moghaddam, S. S.; Alavi Moghaddama, M. R.; Arami, M. J. Hazard. Mater. 2010, 175, 651.
6. [6]
  Muthuraman, G. Desalination 2011, 277, 7308.
7. [7]
  Kamboh, M. A.; Akoz, E.; Memon, S. Yilmaz, M. Water Air Soil Pollut. 2013, 224, 1424.
8. [8]
  Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780.
9. [9]
  Yuan, Z.; Liang, F. Curr. Org. Chem. 2014, 18, 2016.
10. [10]
  Rebek, J. Chem. Commun. 2000, 637.
11. [11]
  Guo, D. S.; Liu, Y. Chem. Soc. Rev. 2012, 41, 5907.
12. [12]
  Akceylan, E.; Bahadir, M.; Yilmaz, M. J. Hazard. Mater. 2009, 162, 960.
13. [13]
  Yilmaz, E. O.; Sirit, A.; Yilmaz, M. J. Macromol. Sci. A: Pure Appl. Chem. 2007, 44, 167.
14. [14]
  Yilmaz, A.; Yilmaz, E.; Yilmaz, M. Dyes Pigm. 2007, 74, 54.
15. [15]
  Kamboh, M. A.; Solangi, I. B.; Sherazi, S. T. H. Desalination 2011, 268, 83.
16. [16]
  Kamboh, M. A.; Solangi, I. B.; Memon, S. J. Hazard. Mater. 2011, 186, 651.
17. [17]
  Akceylan, E.; Erdemir, S. J. Inclusion Phenom. Macrocyclic Chem. 2015, 82, 471.
18. [18]
  Bandela, A. K.; Hinge, V. K.; Yarramala, D. S.; Rao, C. P. ACS Appl. Mater. Interfaces 2015, 7, 11555.
19. [19]
20. [20]
21. [21]
  Fang, X. T.; Guo, H. Y.; Yang, F. F.; Bai, X. Y. Chem. Res. Chin. Univ. 2015, 31, 1051.
22. [22]
  Guo, H. Y.; Yang, F. F.; Jiao, Z. Y.; Lin, J. R. Chin. Chem. Lett. 2013, 24, 450.
23. [23]
  Geng, X. T.; Zhu, S. Y.; Guo, H. Y.; Yang, F. F. J. Inclusion Phenom. Macrocyclic Chem. 2015, 82, 93.
24. [24]
  Tsai, C. C.; Ho, I. T.; Chu, J. H.; Shen, L. C.; Huang, S. L.; Chung, W. S. J. Org. Chem. 2012, 77, 2254.
25. [25]
  Yang, F. F.; Hong, B. Q.; Chai, X. F.; Yin, F. J.; Chen, Y. Y. Supramol. Chem. 2009, 21, 691.
26. [26]
  Yang, F. F.; Zheng, X. H.; Guo, H. Y.; Liu, Z. H.; Guo, Y. J. Inclusion Phenom. Macrocyclic Chem. 2008, 62, 371.
27. [27]
28. [28]
  Guo, H. Y.; Yang, F. F.; Yuan, J.; Bai, X. Y. J. Iran. Chem. Soc. 2015, 12, 197.
29. [29]
  Jin, C. M.; Lu, G. Y., Liu,Y.; You, X. Z.; Wang, Z. H.; Wu, H. M. Chin. J. Chem. 2002, 20, 1080.
30. [30]
  Renny, J. S.; Tomasevich, L. L.; Tallmadge, E. H.; Collum, D. B. Angew. Chem., Int. Ed. 2013, 52, 2.
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