New ICT probes: synthesis and photophysical studies of N-phenylaza-15-crown-5 aryl/heteroaryl oxadiazoles under acidic condition and in the presence of selected metal ions

Tetrahedron

Volumn 63, Issue 7, 2007, Pages 1680-1688

  Mashraqui, Sabir H ^a   Subramanian Sundaram, ^a   Bhasikuttan, A C ^b  

^a UNIVERSITY OF MUMBAI   (India)

^b BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Alkali and alkaline earth cations; Excited state lifetime; Intramolecular charge transfer transition; N Phenylaza 15 crown 5 aryl heteroaryl oxadiazole; Optical spectral studies; Solvatochromism

Indexed keywords

BARIUM; CALCIUM; CATION; IODINE; MAGNESIUM; METAL ION; NITROGEN; OXADIAZOLE DERIVATIVE; POTASSIUM; SODIUM; TRIFLUOROACETIC ACID;

ACIDITY; ARTICLE; CALCIUM BINDING; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; FLAME PHOTOMETRY; INTRAMOLECULAR CHARGE TRANSFER PROBE; MOLECULAR PROBE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON TRANSPORT; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 33846245525     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.11.094     Document Type: Article

References (72)

1. Czarnik A.W. In: Czarnik A.W. (Ed). Fluorescent Chemosensors for Ion and Molecule Recognition. ACS Symposium Series Vol. 538 (1992), American Chemical Society, Washington, DC 104-129
2. Rettig W., and Lapouyade R. In: Lakowicz J.R. (Ed). Probe Design and Chemical Sensing. Topics in Fluorescence Spectroscopy Vol. 4 (1994), Plenum, New York, NY and London 109-149
3. For recent reviews:
4. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515
5. Valeur B. In: Desvergne J.-P., and Czarnik A.W. (Eds). Chemosensors of Ion and Molecule Recognition. NATO ASI Series C Vol. 492 (1997), Kluwer Academic, Dordrecht 195
6. Rurack K., and Resch-Genger U. Chem. Soc. Rev. 31 (2002) 116
7. Valeur B., and Leray I. Coord. Chem. Rev. 205 (2000) 3
8. For selected PET/excimer sensors:
9. Jun E.J., Won H.N., Kim J.S., Lee K.-H., and Yoon J. Tetrahedron Lett. 47 (2006) 4577
10. Kang J., Choi M., Kwon J.Y., Lee E.Y., and Yoon J. J. Org. Chem. 67 (2002) 4384
11. Sankaran N.B., Banthia S., Das A., and Samanta A. New J. Chem. 26 (2002) 1529
12. Burdette S.C., Walkup G.K., Spinger B., Tsien R.Y., and Lippard S.J. J. Am. Chem. Soc. 123 (2001) 7831
13. Jiang P., and Guo Z. Coord. Chem. Rev. 248 (2004) 205
14. Kondo S., Kinjo T., and Yano Y. Tetrahedron Lett. 46 (2005) 3183
15. For coumarin based sensors:
16. Kateinopoulos H.E. Curr. Pharm. Des. 10 (2004) 3835
17. Li H., Xie H., Wang P., and Wu S. New J. Chem. 24 (2000) 105
18. Bourson J., Pouget J., and Valeur B. J. Phys. Chem. 97 (1993) 4552
19. Chen C.-T., and Huang W.-P. J. Am. Chem. Soc. 124 (2002) 6246
20. For styryl based sensors:
21. Letard J.F., Lapouyade R., and Rettig W. Pure Appl. Chem. 65 (1993) 1705
22. Rurack K., Rettig W., and Resch-Genger U. Chem. Commun. (2000) 407
23. For benzothiazole based sensors:
24. Rurack K., Bricks J.L., Reck G., Radeglia R., and Resch-Genger U. J. Phys. Chem. 104 (2000) 3087
25. Mashraqui S.H., Kumar S., and Vashi D. J. Inclusion Phenom. Macro. Chem. 48 (2004) 125
26. Mateeva N., Deligeorgiev T., and Miteva M. J. Inclusion Phenom. Mol. Recognit. Chem. 17 (1994) 81
27. Lednev I.K., Hester R.E., and Moore J.N. J. Am. Chem. Soc. 119 (1997) 3456
28. For 8-hydroxyquinoline based sensors:
29. Mei Y., Bentley P.A., and Wang W. Tetrahedron Lett. 47 (2006) 2447
30. Zhang L., and Meggers E. J. Am. Chem. Soc. 127 (2005) 74
31. Kawakami J., Ohta M., Yamauchi Y., and Ohzeki K. Anal. Sci. 19 (2003) 1353
32. Martins A.O., de Silva E.L., Laranjeira M.C.M., and de Favere V.T. Microchim. Acta 150 (2005) 27
33. Zhang H., Hand L.-F., Zachariasse K.A., and Jiang Y.-B. Org. Lett. 7 (2005) 4217
34. Mei Y., and Bentley P.A. Bioorg. Med. Chem. Lett. 16 (2006) 3131
35. Mitschke U., and Bäuerle P. J. Mater. Chem. 10 (2000) 1471
36. Mashraqui S.H., Kenny R.S., Shailesh G.G., Krishnan A., Bhattacharya M., and Das P.K. Opt. Mater. 27 (2004) 257
37. Yang N.C., Jeong J.K., and Suh D.H. Chem. Lett. 32 (2003) 40
38. Tsien R.Y. Annu. Rev. Biophys. Bioeng. 12 (1983) 91
39. Henquin C., Tamagawa T., Nenquin M., and Cogneau M. Nature 301 (1983) 73
40. Takahashi A., Camacho P., Lechleiter J.D., and Herman B. Physiol. Rev. 79 (1999) 1089
41. Csordas G., and Hajnoczky G. J. Biol. Chem. 278 (2003) 42273
42. Leite M.F., Thrower E.D., Echevarria W., Koulen P., Hirata K., Bennett A.M., Ehrlich B.E., and Nathanson M.H. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 2975
43. Lewis J.D., and Moore J.N. J. Chem. Soc., Dalton Trans. (2004) 1376 and references cited therein
44. Yoshida K., Mori T., Wanatabe S., Kawai H., and Nagamura T. J. Chem. Soc., Perkin Trans. 2 (1999) 393
45. Rurack K., Bricks J.L., Kachkovski A., and Resch U. J. Fluoresc. 7 (1997) 63S
46. Jonker A., Ariese F., and Verhoeven J.W. Recl. Trav. Chim. Pays-Bas 108 (1989) 109
47. Dix J.P., and Vögtle F. Chem. Ber. 113 (1980) 457
48. Reddy P.S.N., and Reddy P. Indian J. Chem., Sect. B 26 (1987) 890
49. Valeur B. In: Schulman S.G. (Ed). Molecular Luminescence Spectroscopy (1993), Wiley, New York, NY 25-84 Part 3
50. Valeur B., Bourson J., and Pouget J. In: Czarnik A.W. (Ed). Fluorescent Chemosensors for Ion and Molecular Recognition. ACS Symposium Series Vol. 538 (1993), American Chemical Society, Washington, DC 25-44
51. Brzezinski B., Schroeder G., Rabold A., and Zundel G. J. Phys. Chem. 99 (1995) 8519
52. Gunnlaugsson T., and Leonard J.P. J. Chem. Soc., Perkin Trans. 2 (2002) 1980
53. Gunnlaugsson T., Nieuwenhuyzen M., Richard L., and Thoss V. J. Chem. Soc., Perkin Trans. 2 (2002) 141
54. Andon R.J.L., Cox J.D., and Herington E.F.G. Trans. Faraday Soc. 50 (1954) 918
55. Meetwa N., Enchev V., Antonov L., Deligeorgiev T., and Mitewa M. J. Inclusion Phenom. Mol. Recognit. Chem. 20 (1995) 323
56. Jones II G., Jackson W.R., Choi C.-Y., and Bergmark W.R. J. Phys. Chem. 89 (1985) 294
57. Rettig W. Top. Curr. Chem. 169 (1994) 165
58. Rurack K., Dekhtyar M.L., Bricks J.L., Resch-Genger U., and Rettig W. J. Phys. Chem. A 103 (1999) 9626
59. Dey J.K., and Dogra S.K. Bull. Chem. Soc. Jpn. 64 (1991) 3142
60. Petkov I., Deligeorgiev T., and Timtcheva I. Dyes Pigments 35 (1997) 171
61. Löhr H.G., and Vögtle G. Acc. Chem. Res. 18 (1985) 65
62. Fery-Forgues S., Le Bris M.T., Guette J.P., and Valeur B. J. Phys. Chem. 92 (1988) 6233
63. Mohanty J., Bhasikuttan A.C., Nau W.M., and Pal H. J. Phys. Chem. B 110 (2006) 5132
64. Pedersen C.J., and Frendsdorff H.K. Angew. Chem., Int. Ed. Engl. 11 (1972) 16
65. Pacey G.E., and Wu Y.P. Talanta 31 (1984) 165
66. Bourson J., and Valeur B. J. Phys. Chem. 93 (1989) 3871
67. Mathevet R., Jonusauskas G., Rulliere C., Letard J.-F., and Lapouyade R. J. Phys. Chem. 9 (1995) 15709
68. Chattopadhyay N., Serpa C., Pereira M.M., de Melo J.S., Arnaut L.G., and Formosinho S.J. J. Phys. Chem. A 105 (2001) 10025
69. Kosower E.M. Acc. Chem. Res. 15 (1982) 259
70. Siebrand W. J. Phys. Chem. 47 (1967) 2441
71. Siebrand W. J. Chem. Phys. 46 (1967) 440
72. Lee D.W., Kwon K.-Y., Jung II J., Park Y., Kim Y.-R., and Hwang I.-W. Chem. Mater. 13 (2001) 565