F--Induced 'turn-on' fluorescent chemosensor based on 1,3-alt thiacalix[4]arene

Tetrahedron

Volumn 65, Issue 22, 2009, Pages 4340-4344

  Kumar, Manoj ^a   Kumar, Rajesh ^a   Bhalla, Vandana ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Fluoride; Fluorogenic chemosensor; Thiacalix 4 arene

Indexed keywords

CALIXARENE; FLUORESCENT DYE; FLUORIDE ION; THIACALIX[4]ARENE; UNCLASSIFIED DRUG;

ARTICLE; BIOSENSOR; FLUORESCENCE ANALYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 65249115855     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.074     Document Type: Article

References (101)

1. Sessler J.L., and Davis J.M. Acc. Chem. Res. 34 (2001) 989-997
2. Gale P.A. Coord. Chem. Rev. 199 (2000) 181-233
3. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486-516
4. Gale P.A. Coord. Chem. Rev. 213 (2001) 79-128
5. Suksai C., and Tuntulani T. Chem. Soc. Rev. 32 (2003) 192-202
6. Martinez-Manez1 R., and Sancenón F. J. Fluoresc. 15 (2005) 267-285
7. Gunnlaugsson T., Glynn M., Tocci G.M., Kruger P.E., and Pfeffer F.M. Coord. Chem. Rev. 250 (2006) 3094-3117
8. Kirk K.L. Biochemistry of Halogens and Inorganic Halides (1991), Plenum, New York, NY p 58
9. Kleerekoper M. Endocrinol. Metab. Clin. North Am. 27 (1998) 441-452
10. Waldbott G. Clin. Toxicol. 18 (1981) 531-541
11. Matuso S., Kiyomiya K.-i., and Kurebe M. Arch. Toxicol. 72 (1998) 798-806
12. Zhang S.-W., and Swager T.M. J. Am. Chem. Soc. 125 (2003) 3420-3421
13. Riggs B.L. J. Bone Miner. Res. (1984) 366-393
14. Laisalmi M., Kokki H., Soikkeli A., Markkanen H., Yli-Hankala A., Rosenberg P., and Lindgren L. Acta Anaesthesiol. Scand. 50 (2006) 982-987
15. Wiseman A. Handbook of Experimental Pharmacology XX/2 (1970), Springer, Berlin Part 2, pp 48-97
16. Weatherall J.A. Pharmacology of Fluorides. Handbook Experimental Pharmacology XX/1 (1969), Springer, Berlin Part 1, pp 141-172
17. Dreisbuch R.H. Handbook of Poisoning (1980), Lange Medical, Los Altos, CA
18. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515-1566
19. Fabbrizzi L., and Poggi A. Chem. Soc. Rev. 24 (1995) 197-202
20. Valeur B., and Leray I. Inorg. Chim. Acta 360 (2007) 765-774
21. Kim S.H., Kim H.J., Yoon J., and Kim J.S. In: Vicens J., and Harrowfield J. (Eds). Calixarenes in the Nanoworld (2007), Springer, Dordrecht, The Netherlands Chapter 15
22. Valeur B., Bourson J., Pouget J., and Czarnik A.W. Fluorescent Chemosensors for Ion and Molecule Recognition. ACS Symposium Series 538 (1993), American Chemical Society, Washington, DC
23. Sharp S.L., Warmack R.J., Goudonnet J.P., Lee I., and Ferrell T.L. Acc. Chem. Res. 26 (1993) 377-382
24. Dusemund C., Sandanayake K.R.A.S., and Shinkai S. J. Chem. Soc., Chem. Commun. (1995) 333-334
25. Yamamoto H., Ori A., Ueda K., Dusemund C., and Shinkai S. Chem. Commun. (1996) 407-408
26. Scherer M., Sessler J.L., Gebauer A., and Lynch V. Chem. Commun. (1998) 85-86
27. Anzenbacher Jr. P., Juriskova K., Lynch V.M., Gale P.A., and Sessler J.L. J. Am. Chem. Soc. 121 (1999) 11020-11021
28. Nicolas M., Fabre B., and Simonet J. Chem. Commun. (1999) 1881-1882
29. Camiolo S., and Gale P.A. Chem. Commun. (2000) 1129-1130
30. Lee D.H., Im J.H., Lee J.H., and Hong H.I. Tetrahedron Lett. 43 (2002) 9637-9640
31. Yun S., Ihm H., Kim H.G., Lee C.W., Indrajit B., Oh K.S., Gong Y.J., Lee J.W., Yoon J., Lee H.C., and Kim K.S. J. Org. Chem. 68 (2003) 2467-2470
32. Valeur B., and Leray I. Coord. Chem. Rev. 205 (2000) 3-40
33. Nohta H., Satozono H., Koiso K., Yoshida H., Ishida J., and Yamaguchi M. Anal. Chem. 72 (2000) 4199-4202
34. Okamoto A., Ichiba T., and Saito I. J. Am. Chem. Soc. 126 (2004) 8364-8365
35. Bianchi A., and Bowman-James K. In: Garcia-Espana E. (Ed). Supramolecular Chemistry of Anions (1997), Wiley-VCH, New York, NY
36. Hay B.P., Firman T.K., and Moyer B.A. J. Am. Chem. Soc. 127 (2005) 1810-1819
37. Bordwell F.G. Acc. Chem. Res. 21 (1988) 456-463
38. Fabbrizzi L., Faravelli H., Franzese G., Licchelli M., Perotti A., and Taglietti A. Chem. Commun. (1998) 971-972
39. Cooper C.R., Spencer N., and James T.D. Chem. Commun. (1998) 1365-1366
40. Arimori S., Davidson M.G., Fyles T.M., Hibbert T.G., James T.D., and Kociok-Köhn G.I. Chem. Commun. (2004) 1640-1641
41. Galbraith E., Fyles T., Marken M.F., Davidson M.G., and James T.D. Inorg. Chem. 47 (2008) 6236-6244
42. Kim S.K., and Yoon J. Chem. Commun. (2002) 770-771
43. Lakowicz J.R. Principles of Fluorescence Spectroscopy. 2nd ed. (1999), Kluwer Academic/Plenum, New York, NY pp 238-264
44. Tong H., Wang L., Jing X., and Wang F. Macromolecules 36 (2003) 2584-2586
45. Lu H., Xu W., Zhang D., Chen C., and Zhu D. Org. Lett. 7 (2005) 4629-4632
46. Lee J.Y., Cho E.J., Mukamel S., and Nam K.C. J. Org. Chem. 69 (2004) 943-950
47. Xu G., and Tarr M.A. Chem. Commun. (2004) 1050-1051
48. Oton F., Tárraga A., Velasco M.D., Espinosa A., and Molina P. Chem. Commun. (2004) 1658-1659
49. Liu C., Qian X., Sun G., Zhao L., and Li Z. New J. Chem. 32 (2008) 472-476
50. Hudnall T.W., and Gabbai F.P. Chem. Commun. (2008) 4596-4597
51. Panzella L., Pezzella A., Arzillo M., Manini P., Napolitano A., and d'Ischia M. Tetrahedron 65 (2009) 2032-2036
52. Swamy K.M.K., Lee Y.J., Lee H.N., Chun J., Kim Y., Kim S.-J., and Yoon J. J. Org. Chem. 71 (2006) 8626-8628
53. Koskela S.J.M., Fyles T.M., and James T.D. Chem. Commun. (2005) 945-947
54. Kim T.H., Choi M.S., Sohn B.-H., Park S.-Y., Lyoo W.S., and Lee T.S. Chem. Commun. (2008) 2364-2366
55. Jun E.J., Swamy K.M.K., Bang H., Kim S.-J., and Yoon J. Tetrahedron Lett. 47 (2006) 3103-3106
56. Xu Z., Kim S., Kim H.N., Han S.J., Lee C., Kim J.S., Qian X., and Yoon J. Tetrahedron Lett. 48 (2007) 9151-9154
57. Gutsche C.D. Calixarenes. In: Stoddart J.F. (Ed). Monographs in Supramolecular Chemistry Vol. 1 (1989), Royal Society of Chemistry, Cambridge, UK
58. In: Vicens J., and Bohmer V. (Eds). Calixarenes: A Versatile Class of Macrocyclic Compounds (1991), Kluwer, Dordrecht, The Netherlands
59. Gutsche C.D. Calixarenes Revisited. Monographs in Supramolecular Chemistry Vol. 6 (1998), The Royal Society of Chemistry, Cambridge, UK
60. In: Vicens J., Asfari Z., and Harrowfield J.M. (Eds). Calixarenes 50th Anniversary: Commemorative Issue (1994), Kluwer Academic, Dordrecht, The Netherlands
61. Calixarene Molecules for Separations. In: Lumetta G.J., and Rogers R.D. (Eds). ACS Symposium Series (1999), American Chemical Society, Washington, DC
62. Kim J.S., and Quang D.T. Chem. Rev. 107 (2007) 3780-3799
63. Lee M.H., Quang D.T., Jung H.S., Yoon J., Lee C.-H., and Kim J.S. J. Org. Chem. 72 (2007) 4242-4245
64. Miyaji H., Sato W., and Sessler J.L. Angew. Chem., Int. Ed. 39 (2000) 1777-1780
65. Piateka P., and Jurczak J. Chem. Commun. (2002) 2450-2451
66. Ludwig R. Fresenius' J. Anal. Chem. 367 (2000) 103-128
67. Chellappan K., Singh N.J., Hwang I.C., Lee J.W., and Kim K.-S. Angew. Chem., Int. Ed 44 (2005) 2899-2903
68. Kim H.J., Kim S.K., Lee J.Y., and Kim J.S. J. Org. Chem. 71 (2006) 6611-6614
69. Miao R., Zheng Q.-Y., Chen C.-F., and Huang Z.-T. Tetrahedron Lett. 46 (2005) 2155-2158
70. Lee S.H., Kim S.H., Kim S.K., Jung J.H., and Kim J.S. J. Org. Chem. 70 (2005) 9288-9295
71. Lee S.H., Kim H.J., Lee Y.O., Vicens J., and Kim J.S. Tetrahedron Lett. 47 (2006) 4373-4376
72. Kim S.K., Bok J.H., Bartsch R.A., Lee J.Y., and Kim J.S. Org. Lett. 7 (2005) 4839-4842
73. Schazmann B., Alhashimy N., and Diamond D. J. Am. Chem. Soc. 128 (2006) 8607-8614
74. Liu S.-Y., He Y.-B., Wu J.-L., Wei L.-H., Qin H.-J., Meng L.-Z., and Hu L. Org. Biomol. Chem. 2 (2004) 1582-1586
75. Kumagai H., Hasegawa M., Miyanari S., Sugawa Y., Sato Y., Hori T., Ueda S., Kameyama H., and Miyano S. Tetrahedron Lett. 38 (1997) 3971-3972
76. Iki N., and Miyano S. J. Inclusion Phenom. 41 (2001) 99-105
77. Morohashi N., Narumi F., Iki N., Hattori T., and Miyano S. Chem. Rev. 106 (2006) 5291-5316
78. Shokova E.A., and Kovalev V.V. Russ. J. Org. Chem. 39 (2003) 1-28
79. Hu X., Xia N., Ye F., Ren J., and Shi X. Spectrochim. Acta, Part A 60 (2004) 1427-1430
80. Lhotak P. Eur. J. Org. Chem. (2004) 1675-1692
81. Lhotak P., Svoboda J., and Stibor I. Tetrahedron 62 (2006) 1253-1257
82. Lang K., Curinova P., Dudic M., Proskova P., Stibor I., St'astny V., and Lhotak P. Tetrahedron Lett. 46 (2005) 4469-4472
83. Zlaatuskova P., Stibor I., Tkadlecova M., and Lhotak P. Tetrahedron 60 (2004) 11383-11390
84. Dhir A., Bhalla V., and Kumar M. Org. Lett. 10 (2008) 4891-4894
85. Kumar R., Bhalla V., and Kumar M. Tetrahedron 64 (2008) 8095-8101
86. Mahajan R.K., Kaur R., Bhalla V., Kumar M., Hattori T., and Miyano S. Sens. Actuators, B 130 (2008) 290-294
87. Bhalla V., Babu J.N., Kumar M., Hattori T., and Miyano S. Tetrahedron Lett. 48 (2007) 1581-1585
88. Bhalla V., Kumar M., Katagiri H., Hattori T., and Miyano S. Tetrahedron Lett. 46 (2005) 121-124
89. Kumar M., Sharma (nee Bhalla) V., and Babu J.N. Tetrahedron 59 (2003) 3267-3273
90. Babu J.N., Bhalla V., Kumar M., Puri R.K., and Mahajan R.K. New J. Chem. 33 (2009) 675-681
91. Babu J.N., Bhalla V., Kumar M., Mahajan R.K., and Puri R.K. Tetrahedron Lett. 49 (2008) 2772-2775
92. Babu J.N., Bhalla V., Kumar M., and Singh H. Lett. Org. Chem. 3 (2006) 787-793
93. Long G.L., and Winefordner J.D. Anal. Chem. 55 (1983) 712A-714A
94. Jung H.S., Kim H.J., Vicens J., and Kim J.S. Tetrahedron Lett. 50 (2009) 983-987
95. Xie H., Yi S., Yang X., and Wu S. New J. Chem. 23 (1999) 1105-1110
96. Bernardo M.A., Alves S., Pina F., De Melo J.S., Albelda M.T., Garcia-España E., Llinares J.M., Soriano C., and Luis S.V. Supramol. Chem. 13 (2001) 435-445
97. Albelda M.T., Bernardo M.A., Diaz P., García-España E., de Melo J.S., Pina F., Soriano C., and Luis S.V. Chem. Commun. (2001) 1520-1521
98. de Melo J.S., Albelda M.T., Diaz P., García-España E., Lodeiro C., Alves S., Lima J.C., Pina F., and Soriano C. J. Chem. Soc., Perkin Trans. 2 (2002) 991-998
99. Mei M., and Wu S. New J. Chem. 25 (2001) 471-475
100. Lin Z.H., Xie L.X., Zhao Y.G., Duan C.Y., and Qu J.P. Org. Biomol. Chem. 5 (2007) 3535-3538
101. Gampp H., Maeder M., Meyer C.J., and Zuberbulher A.D. Talanta 32 (1985) 95-101