Anthracene-based macrocyclic fluorescent chemosensor for selective sensing of dicarboxylate

Tetrahedron Letters

Volumn 50, Issue 1, 2009, Pages 85-88

  Ghosh, Kumaresh ^a   Sarkar, Avik Ranjan ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

1,4 Phenylenediacetate; Anthracene based macrocycle; Charged binding site; Dicarboxylate ion recognition; Excimer formation

Indexed keywords

1,4 PHENYLENEDIACETATE; ACETOACETIC ACID; ANTHRACENE; DICARBOXYLIC ACID; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; SENSOR; SYNTHESIS;

EID: 56949091564     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.135     Document Type: Article

References (26)

1. Martinez-Manez R., and Sancenon F. Chem. Rev. 13 (2003) 4419-4476
2. Suksai C., and Tuntulani T. Chem. Soc. Rev. 32 (2003) 192-202
3. Yoon J., Kim S.K., Singh N.J., and Kim K.S. Chem. Soc. Rev. 35 (2006) 355-360
4. Kim S.K., Singh N.J., Kim S.J., Swamy K.M.K., Kim S.H., Lee K.-H., Kim K.S., and Yoon J. Tetrahedron 61 (2005) 4545-4550
5. Kim Y.K., Lee H.N., Singh N.J., Choi H.J., Xue J.Y., Kim K.S., Yoon J., and Hyun M.H. J. Org. Chem. 73 (2008) 301-304 and references cited therein
6. In: Spichiger-Keller U.S. (Ed). Chemical Sensors and Biosensors for Medical and Biological Applications (1998), Wiley-VCH, Weinheim, Germany
7. Mason, C. F. Biology of Freshwater Pollution, 2nd ed.; Longman: New York, 1991.
8. Voet, D.; Voet, J. G. Biochemistry, 2nd ed.; Wiley: New York, NY, 1995.
9. Kral V., Andrievsky A., and Sessler J.L. J. Am. Chem. Soc. 117 (1995) 2953-2954
10. Gunnlaugsson T., Davis A.P., O'Brien E., and Glynn M. Org. Lett. 4 (2002) 2449-2452 and references cited therein
11. Qin D.-B., Xu F.-B., Wan X.-J., Zhao Y.-J., and Zhang Z.-Z. Tetrahedron Lett. 47 (2006) 5641-5643
12. Kim S.K., Kang B.-G., Koh H.S., Yoon Y.J., Jung S.J., Jeong B., Lee K.-D., and Yoon J. Org. Lett. 6 (2004) 4655-4658
13. Tseng Y.-P., Tu G.-M., Lin C.-H., Chang C.-T., Lin C.-Y., and Yen Y.-P. Org. Biomol. Chem. 5 (2007) 3592-3598 and references cited therein
14. Liu S.-Y., Fang L., He Y.-B., Chan W.-H., Yeung K.-T., Cheng Y.-K., and Yang R.-H. Org. Lett. 7 (2005) 5825-5828
15. Boiocchi M., Bonizzoni M., Fabbrizzi L., Piovani G., and Taglietti A. Angew. Chem., Int. Ed. 43 (2004) 3847-3852
16. Raker J., and Glass T.E. J. Org. Chem. 67 (2002) 6113-6116
17. Sancenon F., Martinez-Manez R., Miranda M.A., Segui M.-J., and Soto J. Angew. Chem., Int. Ed. 42 (2003) 647-650
18. Fabbrizzi L., Foti F., and Tagletti A. Org. Lett. 7 (2005) 2603-2606
19. Ghosh K., Masanta G., and Chattopadhyay A.P. Tetrahedron Lett. 48 (2007) 6129-6132
20. Ghosh K., and Masanta G. Tetrahedron Lett. 49 (2008) 2592-2597
21. Jeong K.-S., and Cho Y.L. Tetrahedron Lett. 38 (1997) 3279-3282
22. Wallance K.J., Belcher W.J., Turner D.R., Syed K.F., and Steed J.W. J. Am. Chem. Soc. 125 (2003) 9699-9715
23. Ghosh K., Sarkar A.R., and Masanta G. Tetrahedron Lett. 48 (2007) 8725-8729
24. Calculations were performed using CS Chem 3D version 6.0.
25. Xu Z., Kim S., Lee K.-H., and Yoon J. Tetrahedron Lett. 48 (2007) 3797-3800
26. a) for the receptor-guest complex shown in Table 1. In a similar way the emission values obtained during fluorescence titration of 1 with the same guests were used to evaluate the binding constant values. Chou P.T., Wu G.R., Wei C.Y., Cheng C.C., Chang C.P., and Hung F.T. J. Phys. Chem. B 104 (2000) 7818