Mesitylene based azo-coupled chromogenic tripodal receptors-a visual detection of Ag(I) in aqueous medium

Tetrahedron

Volumn 62, Issue 33, 2006, Pages 7878-7886

  Bhardwaj, Vimal K ^a   Singh, Narinder ^a   Hundal, Maninder Singh ^a   Hundal, Geeta ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 TRIMETHYLBENZENE; AZO COMPOUND; CADMIUM; CALCIUM ION; CHROMOGENIC SUBSTRATE; COPPER ION; DIOXANE; LEAD; LITHIUM ION; MERCURY; METAL; NICKEL; RECEPTOR SUBUNIT; SILVER; SODIUM ION; STRONTIUM; ZINC ION;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; COLOR; COMPLEX FORMATION; METAL BINDING; PHOTOMETRY; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

EID: 33745625330     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.047     Document Type: Article

References (121)

1. Löhr H.G., and Vögtle F. Acc. Chem. Res. 18 (1985) 65 and references therein
2. Hayashita T., and Takagi M. In: Atwood J.L., Davies J.E.D., MacNicol D.D., Vögtle F., and Suslick K.S. (Eds). Comprehensive Supramolecular Chemistry (1996), Pergamon, Oxford 635-669
3. Kaneda T., Umeda S., Tanigawa H., Misumi S., Kai Y., Morii H., Miki K., and Kasai N. J. Am. Chem. Soc. 107 (1985) 4802-4803
4. Ikeda A., and Shinkai S. Chem. Rev. 97 (1997) 1713-1734
5. Diamond D., and McKervey M.A. Chem. Soc. Rev. 25 (1996) 15-24
6. Gutsche C.D. Calix[4]arenes revisited (1998), The Royal Society of Chemistry, Cambridge, UK 164-165
7. Takagi M., Nakamura H., and Ueno K. Anal. Lett. 10 (1977) 1115
8. Gunnlaugsson T., and Leonard J.P. J. Chem. Soc., Perkin Trans. 2 (2002) 1980-1985
9. Gunnlaugsson T., Nieuwenhuyzen M., Richard L., and Thoss V. J. Chem. Soc., Perkin Trans. 2 (2002) 141-150
10. Gunnlaugsson T., Nieuwenhuyzen M., Richard L., and Thoss V. Tetrahedron Lett. 42 (2001) 4725-4728
11. Dix J.P., and Vögtle F. Angew. Chem., Int. Ed. Engl. 17 (1978) 857-859
12. Gostokowski M.L., McDaniel J.B., Wei J., Curey T.E., and Shear J.B. J. Am. Chem. Soc. 120 (1998) 18-22
13. Fodor S.P.A., Rava R.P., Huang X.C., Pease A.C., Holmes C.P., and Adams C.L. Nature 364 (1993) 555-556
14. Malmqvist M. Nature 361 (1993) 186-190
15. de Silva A.P., McCaughan B., McKinney B.O.F., and Querol M. Dalton Trans. (2003) 1902-1913
16. Amendola V., Fabbrizzi L., Mangano C., and Pallavicini P. Acc. Chem. Res. 34 (2001) 488-493
17. Czarnik A.W. Acc. Chem. Res. 27 (1994) 302-308
18. 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) 1515-1566
19. Spichiger-Keller U.S. Chemical Sensors and Biosensors for Medical and Biological Applications (1998), Wiley-VCH, Weinheim, Germany
20. Czarnik A.W. Fluorescent Chemosensors for Ion and Molecular recognition (1993), American Chemical Society, Washington, DC
21. Desvergne J.P., and Czarnik A.W. Chemosensors for ion and Molecule Recognition. NATO Asi Series (1997), Kluwer Academic Publishers, London Series C
22. Martínez-Mánez R., and Sancenón F. Chem. Rev. 103 (2003) 4419-4476
23. In: Wolbeis O.S. (Ed). Fiber Optic Chemical Sensors and Biosensors (1991), CRC, Boca Raton, FL
24. Seiler K., and Simon W. Sens. Actuators, B 6 (1992) 295-298
25. Kao T.-L., Wang C.-C., Pan Y.-T., Shiao Y.-J., Yen J.-Y., Shu C.-M., Lee G.-H., Peng S.-M., and Chung W.-S. J. Org. Chem. 70 (2005) 2912-2920
26. Shinkai S., Araki K., Shibata J., and Manabe O. J. Chem. Soc., Perkin Trans. 1 (1989) 195-196
27. Shinkai S., Araki K., Shibata J., Tsugawa D., and Manabe O. J. Chem. Soc., Perkin Trans. 1 (1990) 333-337
28. Nomura E., Taniguchi H., and Ttamura S. Chem. Lett. (1989) 1125-1126
29. Hamaguchi S., Kotani K., and Yoshida K. Tetrahedron Lett. 2 (1991) 7419-7420
30. McCarrick M., Wu B., Harris S.J., Diamond D., Barret G., and McKervey M.A. J. Chem. Soc., Chem. Commun. (1992) 1287-1288
31. Nomura E., Taniguchi H., and Otsuji Y. Chem. Express 7 (1992) 685-688
32. Morita Y., Agawa T., Nomura E., and Taniguchi H. J. Org. Chem. 57 (1992) 3658-3662
33. McCarrick M., Wu B., Harris S.J., Diamond D., Barret G., and McKervey M.A. J. Chem. Soc., Perkin Trans. 2 (1993) 1963-1968
34. Kubo Y., Hamaguchi S., Niimi A., Yoshida K., and Tokita S. J. Chem. Soc., Chem. Commun. (1993) 305-306
35. Kubo Y., Maeda S., Nakamura M., and Tokita S. J. Chem. Soc., Chem. Commun. (1994) 1725-1726
36. Kubo Y., Maruyama S., Ohhara N., Nakamura M., and Tokita S. J. Chem. Soc., Chem. Commun. (1995) 1727-1728
37. Chawla H.M., and Srinivas K. J. Org. Chem. 61 (1996) 8464-8470
38. See Ref. 1d.
39. Bitter I., Grün A., Toth G., Szollosy A., Horvath Gy., Agai B., and Toke L. Tetrahedron 52 (1996) 639-646
40. Ji H., Brown G.M., and Dabestani R. J. Chem. Soc., Chem. Commun. (1999) 609-610
41. Talanora G., Elkarim N.S.A., Talanova V.S., and Bartsch R.A. Anal. Chem. 71 (1999) 3106-3109
42. Gordon J.L.M., Böhmer V., and Vögt W. Tetrahedron Lett. 36 (1995) 2445-2448
43. Kim M.Y., and Chang S.K. J. Org. Chem. 63 (1998) 2362-2364
44. Leray I., Lefevre J.P., Delouis J.F., Delaire J., and Valeur B. Chem.-Eur. J. 7 (2001) 4590-4598
45. Ma Q.L., Ma H.M., Wang Z.H., Su M.H., Xiao H.Z., and Liang S.C. Chem. Lett. (2001) 100-102
46. Liu Y., Wang H., Wang L.H., Li Z., Zhang H.Y., and Zhang Q. Tetrahedron 59 (2003) 7967-7972
47. Choi M.J., Kim M.Y., and Chang S.-K. J. Chem. Soc., Chem. Commun. (2001) 1664-1665
48. Cha N.R., Kim M.Y., Kim Y.H., Choe J.I., and Chang S.K. J. Chem. Soc., Perkin Trans. 2 (2002) 1193-1196
49. Kim J.S., Shon O.K., Yang S.H., Kim J.Y., and Kim M.J. J. Org. Chem. 67 (2002) 6514-6518
50. Kim J.Y., Kim G., Kim C.R., Lee S.H., Lee J.H., and Kim J.S. J. Org. Chem. 68 (2003) 1933-1937
51. Lee S.H., Kim J.Y., Ko J., Lee J.Y., and Kim J.S. J. Org. Chem. 69 (2004) 2902-2905
52. Cram D.J., Carmack R.A., and Helgeson R.C. J. Am. Chem. Soc. 110 (1988) 571-577
53. Helgeson R.C., Czech B.P., Chapoteau E., Gebaver C.R., Kumar A., and Cram D.J. J. Am. Chem. Soc. 111 (1989) 6339-6350
54. Czech B.P., Chapoteau E., Chimenti M.Z., Zazulak W., Gebaver C.R., and Kumar A. Anal. Chim. Acta 263 (1992) 159-167
55. Czech B.P., Chapoteau E., Zazulak W., Gebaver C.R., and Kumar A. Anal. Chim. Acta 241 (1990) 127-136
56. Klink, R.; Bodart, D.; Lehn, J-M.; Helfert, B.; Bitsch, R. Eur. Patent 85320, 1983.
57. Chapoteau E., Czech B.P., Gebaver C.R., Kumar A., Leong K., Mtych D.T., Zazulak W., Desai D.H., Luboch E., Krzykwaski J., and Bartsch R.A. J. Org. Chem. 56 (1991) 2575-2579
58. Zazulak W., Chapoteau E., Czech B.P., and Kumar A. J. Org. Chem. 57 (1992) 6720-6727
59. Oueslati F., Dumazet-Bonnamour I., and Lamartine R. New J. Chem. 27 (2003) 644-647
60. Coranado E., Galán-Mascarós J.R., Marti-Gastaldo C., Palomares E., Durrant J.R., Vilar R., Gratzel M., and Nazeeruddin M.K. J. Am. Chem. Soc. 127 (2005) 12351-12356
61. Gunnlaugsson T., Leonard J.P., and Murray N.S. Org. Lett. 6 (2004) 1557-1560
62. Gunnlaugsson T., Lee C.T., and Parkesh R. Org. Lett. 5 (2003) 4065-4068
63. Gunnlaugsson T., Lee C.T., and Parkesh R. Org. Biomol. Chem. 1 (2003) 3265-3267
64. Suksai C., and Tuntulani T. Chem. Soc. Rev. 32 (2002) 192-202
65. Lee D.H., Lee K.H., and Hong J.-I. Org. Lett. 3 (2001) 5-8
66. Mohr G.J. Sens. Actuators, B 107 (2005) 2-13
67. Garcia-Acosta B., Albiach-Marti X., Garcia E., Gill L., Martinez-Manez R., Rurack K., Sancenon F., and Soto J. Chem. Commun. (2004) 774-775
68. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486-516
69. Gale P.A. Coord. Chem. Rev. 213 (2001) 79-128
70. Gale P.A. Coord. Chem. Rev. 199 (2000) 181-233
71. Rakow N.A., Sen A., Janzen M.C., Ponder J.B., and Soslick K.S. Angew. Chem., Int. Ed. 44 (2005) 4528-4532
72. Mohr G.J. Sens. Actuators, B 90 (2003) 31-36
73. Mohr G.J. Chem.-Eur. J. 10 (2004) 1082-1090
74. Mohr G.J., and Grummt U.-W. J. Photochem. Photobiol., A: Chem. 163 (2004) 341-345
75. Mohr G.J. Dyes Pigments 62 (2004) 77-81
76. Mohr G.J., Wenzel M., Lehmann F., and Czerney P. Anal. Bioanal. Chem. 374 (2002) 399-402
77. Mohr G.J. Anal. Chim. Acta 508 (2004) 233-237
78. James T.D., Sandanayake K.R.A.S., and Shinkai S. Nature 374 (1995) 6520
79. Hunter C.A., and Shannon R.J. Chem. Commun. (1996) 1361-1362
80. Gunnlaugsson T., Kelly J.M., Nieuwenhuyzen M., and O'Brien A.M.K. Tetrahedron Lett. 44 (2003) 8571-8575
81. Braininaa K.Z., Stozhko N.Y., and Shlygina Z.V. J. Anal. Chem. 57 (2002) 945-949
82. Descalzo A.B., Martinez-Maňez R., Redeglia R., Rurack K., and Soto J. J. Am. Chem. Soc. 125 (2003) 3418-3419
83. Yoon J., Ohler N.E., Vance D.H., Aumiller W.D., and Czarnic A.W. Tetrahedron Lett. 38 (1997) 3845-3848
84. Meyer, R. L.; Rusell, D. D.; Scaggs, J.; Knowlton, W. Abstracts of papers, 222nd ACS National Meeting, New Orleans, LA, 2003.
85. Wang X., Lee C., Soo-Hyoung S., Kris J., Kumar J., and Samuelson L. Nano Lett. 2 (2002) 1273-1275
86. Shi G., and Jiang G. Anal. Sci. 18 (2002) 1215-1219
87. Guo X., Qian X., and Jia L. J. Am. Chem. Soc. 126 (2004) 2272-2273
88. Moon S.Y., Cha N.R., Kim Y.H., and Chang S.K. J. Org. Chem. 69 (2004) 181-183
89. Rurack K., Kollmannsberger M., Resch-Genger U., and Daub J. J. Am. Chem. Soc. 122 (2000) 968-969
90. Banthia S., and Samanta A. New J. Chem. 29 (2005) 1007-1010
91. Xu Z., Qian X., and Cui J. Org. Lett. 7 (2005) 3029-3032
92. Wang L., Zhu X.-J., Wong W.-Y., Guo J.-P., Wong W.-K., and Li Z.-Y. J. Chem. Soc., Dalton Trans. (2005) 3235-3240
93. Player T.N., Shinoda S., and Tsukube H. Org. Biomol. Chem. 3 (2005) 1615-1616
94. Gunnlaugsson T., Kruger P.E., Lee T.C., Parkesh R., Pfeffer F.M., and Hussey M.G. Tetrahedron Lett. 44 (2003) 6575-6578
95. Gunnlaugsson T., Davis A.P., and Glynn M. Org. Lett. 4 (2002) 2449-2452
96. Gunnlaugsson T., Bichell B., and Nolan C. Tetrahedron Lett. 43 (2002) 4989-4992
97. Gunnlaugsson T., Davis A.P., and Glynn M. Chem. Commun. (2001) 2556-2557
98. McClure D.S. J. Chem. Phys. 20 (1952) 682-686
99. Lerchi M., Reitter E., Simon W., and Pretsch E. Anal. Chem. 66 (1994) 1713-1717
100. Ishikawa J., Sakamoto H., Mizuno T., Doi K., and Otomo M. Analyst 123 (1998) 201-207
101. Marczenko Z. In: Ramsay G.C. (Ed). Spectrophotometric Determination of Elements (1976), Wiley, New York, NY
102. Paradkar R.P., and Williams R.R. Anal. Chem. 66 (1994) 2752-2756
103. Singh N., Hundal M.S., Hundal G., and Martinez-Ripoll M. Tetrahedron 61 (2005) 7796-7806
104. Singh N., and Hundal G. J. Inclusion Phenom. Macrocycl. Chem. 52 (2005) 253-259
105. Unpublished results given in Ph. D Thesis of Singh, N. Submitted to the Faculty of Sciences, Guru Nanak Dev University, Amritsar, India, 2005.
106. Wiskur S.L., Ait-Haddon H., Lavingne J.J., and Anslyn E.V. Acc. Chem. Res. 34 (2001) 963-972
107. Matzger A., Lynch V.M., and Anslyn E.V. Angew. Chem., Int. Ed. 36 (1997) 862-865
108. Nguyen B.T., Wiskur S.L., and Anslyn E.V. Org. Lett. 6 (2004) 2499-2501
109. Wisbur S.L., Lavigne J.J., Ait-Haddon H., Lynch V., Chiu Y.H., Canam J.W., and Anslyn E.V. Org. Lett. 3 (2001) 1311-1314
110. Wisbur S.L., and Anslyn E.V. J. Am. Chem. Soc. 123 (2001) 10109-10110
111. McClesbey S.C., Griffin M.J., Schneider S.E., McDevitt J.T., and Anslyn E.V. J. Am. Chem. Soc. 125 (2003) 1114-1115
112. Zhong Z., and Anslyn E.V. J. Am. Chem. Soc. 124 (2002) 9014-9015
113. Sun W.Y., Fan J., Okamura T.-A., Xie J., Yu K.B., and Ueyama N. Chem.-Eur. J. 7 (2001) 2557-2562
114. Katayama Y., Fukuda R., and Takagi M. Anal. Chim. Acta 185 (1986) 295-306
115. Katayama Y., Nita K., Ueda M., Nakamura H., and Takagi M. Anal. Chim. Acta 173 (1985) 193-209
116. Wilcox K., and Pacey G.E. Anal. Chim. Acta 245 (1991) 235-242
117. Kimura K., Tanaka M., Iketani S., and Shono T. J. Org. Chem. 52 (1987) 836-844
118. Kimura K., Iketani S., Sakamoto H., and Shono T. Analyst 115 (1990) 1251-1255
119. Vögtle F. Pure Appl. Chem. 52 (1980) 2405-2416
120. Benesi H.A., and Hilderbrand J.H. J. Am. Chem. Soc. 71 (1949) 2703-2704
121. Takagi M. In: Inoue Y., and Gökel G.W. (Eds). Cation Binding by Macrocycles (1990), Dekker, New York, NY 465