Synthesis of novel bis(β-cyclodextrin)s linked with glycol and their inclusion complexation with organic dyes

Helvetica Chimica Acta

Volumn 93, Issue 6, 2010, Pages 1136-1148

  Zhao, Yong ^a   Yang, Yong Cun ^a   Shi, Hao ^a   Zhu, Hong You ^b   Huang, Rong ^b   Chi, Chao Ming ^a   Zhao, Yan ^a  

^a YUNNAN NORMAL UNIVERSITY   (China)

^b YUNNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2D-NMR SPECTROSCOPY; BINDING ABILITIES; BRILLIANT GREEN; COMPLEX STABILITY; COOPERATIVE BINDING MODE; DIETHYLENE GLYCOL; DYE MOLECULE; HYDROGEN SULFATE; INCLUSION COMPLEXATION; MOLECULAR BINDING; NEUTRAL RED; ORGANIC DYE; PHOSPHATE BUFFERS; RECOGNITION MECHANISM; RHODAMINE B; SIZE AND SHAPE; TRIETHYLENE GLYCOL;

AMMONIUM COMPOUNDS; BINDING ENERGY; BIOCHEMISTRY; CHLORINE COMPOUNDS; ETHYLENE; ETHYLENE GLYCOL; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SODIUM; SODIUM SULFATE; SYNTHESIS (CHEMICAL);

DATA STORAGE EQUIPMENT;

AMMONIUM 8 ANILINONAPHTHALENE 1 SULFONATE; BIS(6 HYDROXY 6 DEOXY BETA CYCLODEXTRIN); BIS(BETA CYCLODEXTRIN); CYCLODEXTRIN DERIVATIVE; DYE; GLYCOL; MONO[6 O (4 TOLUENESULFONYL)] BETA CYCLODEXTRIN; N [4 [[4 (DIETHYLAMINO)CYCLOHEXA 2,5 DIEN 1 YL](PHENYL)METHYL]CYCLOHEX 2 EN 1 YLIDENE] N ETHYLETHANAMINIUM HYDROGEN SULFATE; N [6 (METHYLAMINO) 3H XANTHEN 3 YLIDENE]METHANAMINIUM CHLORIDE; N8,N8,3 TRIMETHYLPHENAZINE 2,8 DIAMINE; ORGANIC COMPOUND; RHODAMINE B; SODIUM 6 (4 TOLUIDINYL)NAPHTHALENE 2 SULFONATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; FLUORESCENCE SPECTROSCOPY; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 77954164762     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.200900345     Document Type: Article

References (38)

1. J. Szejtli, 'Cyclodextrins and their Inclusion Complexes', Akademia Kiado, Budapest, 1982.
2. G.Wenz, Angew. Chem., Int. Ed. 1994, 33, 803;
3. S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959.
4. J. Szejtli, T. Osa, in 'Comprehensive Supramolecular Chemistry', Eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle, Elsevier, Oxford, UK, 1996, Vol. 3.
5. R. Breslow, B. Zhang, J. Am. Chem. Soc. 1992, 114, 5882;
6. B. Zhang, R. Breslow, J. Am. Chem. Soc. 1997, 119, 1676;
7. F. Venema, A. E. Rowan, R. J. M. Nolte, J. Am. Chem. Soc. 1996, 118, 257;
8. R. R. French, J. Wirz, W.-D. Woggon, Helv. Chim. Acta 1998, 81, 1521;
9. L. C.West, O.Wyness, B. L. May, P. Clements, S. F. Lincoln, C. J. Easton, Org. Biomol. Chem. 2003, 1, 887.
10. a) R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997;
11. b) R. Breslow, B. Zhang, J. Am. Chem. Soc. 1996, 118, 8495;
12. c) B. Zhang, R. Breslow, J. Am. Chem. Soc. 1993, 115, 9353;
13. d) Y. Liu, C.-C. You, B. Li, Chem. - Eur. J. 2001, 7, 1281;
14. e) Y. Liu, Y. Chen, B. Li, T. Wada, Y. Inoue, Chem. - Eur. J. 2001, 7, 2528;
15. f) Y. Liu, C.-C. You, Y. Chen, T. Wada, Y. Inoue, J. Org. Chem. 1999, 64, 7781.
16. C. J. Easton, S. F. Lincoln, 'Modified Cyclodextrins, Scaffolds and Templates for Supramolecular Chemistry', Imperial College: London, UK, 1999.
17. Y. Liu, Y. Chen, Acc. Chem. Res. 2006, 39, 681;
18. Y. Liu, Y. Song, Y. Chen, Z.-X. Yang, F. Ding, J. Phys. Chem. B 2005, 109, 10717;
19. Y. Liu, L. Li, H.-Y. Zhang, Y. Song, J. Org. Chem. 2003, 68, 527;
20. Y. Liu, X.-Y. Li, D.-S. Guo, H. Chi, Supramol. Chem. 2008, 20, 609;
21. H. F. M. Nelissen, M. C. Feiters, R. J. M. Nolte, J. Org. Chem. 2002, 67, 5901;
22. S. D. P. Baugh, Z. Yang, D. K. Leung, D. M.Wilson, R. Breslow, J. Am. Chem. Soc. 2001, 123, 12488;
23. J. J. Michels, J. Huskens, D. N. Reinhoudt, J. Am. Chem. Soc. 2002, 124, 2056.
24. J. S. Lock, B. L. May, P. Clements, S. F. Lincoln, C. J. Easton, Org. Biomol. Chem. 2004, 2, 337;
25. S.-H. Chiu, D. C. Myles, R. L. Garrell, J. F. Stoddart, J. Org. Chem. 2000, 65, 2792;
26. S. D. P. Baugh, Z. Yang, D. K. Leung, D. M. Wilson, R. Breslow, J. Am. Chem. Soc. 2001, 123, 12488.
27. Y. Zhao, X.-Q. Liu, J. Gu, L.-Q. Wang, H.-Y. Zhu, R. Huang, Y.-F. Wang, Z.-M. Yang, J. Phys. Org. Chem. 2008, 21, 440;
28. Y. Zhao, Z. M. Yang, S. M. Chi, J. Gu, Y. C. Yang, R. Huang, B. J. Wang, H. Y. Zhu, Bull. Korean. Chem. Soc. 2008, 29, 953;
29. Y. Zhao, X. Q. Liu, H. Y. Zhu, Z. M. Yang, R. Huang, Chin. Chem. Lett. 2006, 17, 1543.
30. Y. Zhao, Y. C. Yang, S. M. Chi, H. Shi, Y. Zhao, H. Y. Zhu, Q. L. Li, Y. F. Wang, Helv. Chim. Acta 2010, 93, 999;
31. Y. Zhao, J. Gu, S. M. Chi, Y. C. Yang, H. Y. Zhu, R. Huang, Y. F. Wang, J. Solution Chem. 2009, 38, 417;
32. Y. Zhao, J. Gu, Y. C. Yang, H. Y. Zhu, R. Huang, B. Jing, J. Mol. Struct. 2009, 930, 72.
33. F. Cramer, W. Saenger, H.-C. Spatz, J. Chem. Soc. 1967, 89, 14.
34. Y. Liu, Y. Chen, S.-X. Liu, X.-D. Guan, T.Wada, Y. Inoue, Org. Lett. 2001, 3, 1657;
35. Y. Liu,Y. Chen, L. Li, H.-Y. Zhang, S.-X. Liu, X.-D. Guan, J. Org. Chem. 2001, 66, 8518.
36. T. Jiang, D. K. Sukumaran, S. D. Soni, D. S. Lawrence, J. Org. Chem. 1994, 59, 5149;
37. C. A. Haskard, C. J. Easton, B. L. May, S. F. Lincoln, Inorg. Chem. 1996, 35, 1059.
38. R. C. Petter, J. S. Salek, C. T. Sikorski, G. Kumaravel, F.-T. Lin, J. Am. Chem. Soc. 1990, 112, 3860.