Anthracene coupled trans-pyridylcinnamide: a new fluororeceptor for selective sensing of dicarboxylates

Tetrahedron Letters

Volumn 49, Issue 16, 2008, Pages 2592-2597

  Ghosh, Kumaresh ^a   Masanta, Goutam ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Anthracene; Dicarboxylate recognition; Fluorescent receptor; trans Pyridylcinnamide

Indexed keywords

ANTHRACENE; DICARBOXYLIC ACID DERIVATIVE; PIMELIC ACID; PYRIDINE DERIVATIVE; PYRIDYLCINNAMIDE; UNCLASSIFIED DRUG; UREA;

ARTICLE; BINDING AFFINITY; FLUORESCENCE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

EID: 40849137503     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.095     Document Type: Article

References (32)

1. Schmidtchen F.P. Coord. Chem. Rev. 250 (2006) 2918-2928
2. Amendola V., Esteban-Gomez D., Fabbrizzi L., and Licchelli M. Acc. Chem. Res. 39 (2006) 343-353
3. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419-4476
4. Schmidtchen F.P., and Berger M. Chem. Rev 97 (1997) 1609-1646
5. Voet D., and Voet J.G. Biochemistry. 2nd ed. (1995), Wiley, New York, NY
6. Gunnlaugsson T., Davis A.P., O'Brien J.E., and Glynn M. Org. Lett. 4 (2002) 2449-2452 and references cited therein
7. Kral V., Andrievsky A., and Sessler J.L. J. Am. Chem. Soc. 117 (1995) 2953-2954
8. 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
9. Kacprzak K., and Gawronski J. Chem. Commun. (2003) 1532-1533
10. Goodman M.S., Hamilton A.D., and Weiss J. J. Am. Chem. Soc. 117 (1995) 8447-8455
11. Linton B.R., Goodman M.S., Fan E., van Arman S.A., and Hamilton A.D. J. Org. Chem. 66 (2001) 7313-7319 and references cited therein
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) 4655-4685 and references cited therein
13. Raker J., and Glass T.E. J. Org. Chem. 67 (2002) 6113-6116
14. Jadhav V.D., and Scmidtchen F.P. Org. Lett. 8 (2006) 2329-2332 and references cited therein
15. Desiraju G.R. Acc. Chem. Res. 35 (2002) 565-573
16. Hobza P., and Havlas Z. Chem. Rev. 100 (2000) 4253-4264
17. Steiner T., and Saenger W. J. Chem. Soc., Chem. Commun. (1995) 2087-2088
18. Thallapally P.K., Katz A.K., Carrell H.L., and Desiraju G.R. Cryst. Eng. Commun. 5 (2003) 87-92
19. Schmuck C., and Lex J. Eur. J. Org. Chem. (2001) 1519-1523 and references cited therein
20. Huggins M.T., and Lightner D.A. J. Org. Chem. 66 (2001) 8402-8410
21. Marques M.P.M., da Costa A.M.A., and Ribeiro-Claro P.J.A. J. Phys. Chem. A 105 (2001) 5292-5297
22. Sutor D.J. Nature 195 (1962) 68-69
23. For a recent review on C-H⋯O bonds see: Desiraju, G. R.; Steiner, T. The weak Hydrogen Bonds in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
24. +, 764.9, 651.2.
25. Energy minimization was carried out by MMX (PC Model Serena Software 1993). Molecular modelling was performed using standard constants, and the dielectric constant was maintained at 1.5.
26. Quinn J.R., and Zimmerman S.C. Org. Lett. 6 (2004) 1649-1652 and references cited therein
27. Li Z., Ding J., Robertson G., Day M., and Tao Y. Tetrahedron Lett. 46 (2005) 6499-6502
28. Ghosh K., Masanta G., and Chattopadhyay A.P. Tetrahedron Lett. 48 (2007) 6129-6132
29. Jeong K.-S., and Cho Y.L. Tetrahedron Lett 38 (1997) 3279-3282
30. de Silva A.P., Gunaratne H.Q.N., and McCoy C.P. Nature 364 (1993) 42-44
31. de Silva A.P., and Sandanayake K.R.A.S. Angew. Chem., Int. Ed. Engl. 29 (1990) 1173-1175
32. a) for the receptor-guest complex shown in Table 2. In a similar way the emission values obtained during fluorescence titrations 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.; Hung, F. T. J. Phys. Chem B. 2002, 104, 7818.