Multiple analyte response and molecular logic operations by excited-state charge-transfer modulation in a bipyridine integrated fluorophore

Chemistry - An Asian Journal

Volumn 6, Issue 2, 2011, Pages 430-437

  Sreejith, Sivaramapanicker ^a   Divya, Kizhumuri P ^a   Manojkumar, T K ^b   Ajayaghosh, Ayyappanpillai ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b INDIAN INSTITUTE OF INFORMATION TECHNOLOGY AND MANAGEMENT KERALA   (India)

Author keywords

cations; charge transfer; fluorescence; molecular logic; solvatochromism

Indexed keywords

ANALYTES; BIPYRIDINES; BIPYRIDYL; BOOLEAN LOGIC OPERATIONS; CATIONS; ETHYLENEDIAMINETETRAACETIC ACID; EXCITED-STATE PROPERTIES; FILTER PAPERS; FLUORESCENT SIGNALS; LOGIC OPERATIONS; MICROFLUIDIC TECHNIQUES; MOLECULAR LOGIC; MULTIPLE ANALYTES; MULTIPLE LOGIC; SOLVATOCHROMISMS;

CHARGE TRANSFER; FLUOROPHORES; ION EXCHANGE; MASS TRANSFER; POSITIVE IONS;

EXCITED STATES;

EID: 79251489452     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000637     Document Type: Article

References (96)

1. A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515
2. M. Takeuchi, M. Ikeda, A. Sugasaki, S. Shinkai, Acc. Chem. Res. 2001, 34, 865
3. K. Rurack, U. Resch-Genger, Chem. Soc. Rev. 2002, 31, 116
4. Special Issue on "Luminescent Sensors", Coord. Chem. Rev. 2000, 205
5. Molecular Switches (Ed.:, B. Feringa,), Wiley-VCH, Weinheim, Germany, 2001
6. E. Nolan, S. J. Lippard, Chem. Rev. 2008, 108, 3443
7. K. L. Haas, K. J. Franz, Chem. Rev. 2009, 109, 4921
8. R. McRae, P. Bagchi, S. Sumalekshmy, C. J. Fahrni, Chem. Rev. 2009, 109, 4780.
9. A. Aviram, J. Am. Chem. Soc. 1988, 110, 5687
10. A. P. De Silva, H. Q. N. Guraratne, C. P. McCoy, Nature 1993, 364, 42
11. R. J. Lipton, Science 1995, 268, 542
12. P. Ball, Nature 2000, 406, 118
13. A. P. de Silva, S. Uchiyama, Nat. Nanotechnol. 2007, 2, 399
14. K. Szacilowski, Chem. Rev. 2008, 108, 3481.
15. R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187
16. R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy, K. R. A. S. Sandanayake, Top. Curr. Chem. 1993, 168, 228
17. Y. Li, H. Zheng, Y. Li, S. Wang, Z. Wu, P. Liu, Z. Gao, H. Liu, D. Zhu, J. Org. Chem. 2007, 72, 2878.
18. B. Valeur, I. Leray, Coord. Chem. Rev. 2000, 205, 3
19. J. R. Lakowicz, Anal. Biochem. 2001, 298, 1
20. O. A. Bozdemir, R. Guliyev, O. Buyukcakir, S. Selcuk, S. Kolemen, G. Gulseren, T. Nalbantoglu, H. Boyaci, E. U. Akkaya, J. Am. Chem. Soc. 2010, 132, 8029.
21. For hybrid materials in logic operations, see
22. T. Gupta, M. E. van der Boom, Angew. Chem. 2008, 120, 5402
23. Angew. Chem. Int. Ed. 2008, 47, 5322
24. A. P. de Silva, M. R. James, B. O. F. McKinney, D. A. Pears, S. M. Weir, Nat. Mater. 2006, 5, 787
25. L. F. O. Furtado, A. D. P. Alexiou, L. Gonçalves, H. E. Toma, K. Araki, Angew. Chem. 2006, 118, 3215
26. Angew. Chem. Int. Ed. 2006, 45, 3143
27. W. Zhou, Y. Li, T. Li, H. Liu, S. Wang, C. Li, M. Yuan, X. Liu, D. Zhu, Chem. Asian J. 2006, 1-2, 224.
28. For basic logic operations, see
29. A. P. de Silva, S. S. K. de Silva, N. C. W. Goonesekera, H. Q. N. Gunaratne, P. L. M. Lynch, K. R. Nesbitt, S. T. Paduvathavithana, N. L. D. S. Ramyalal, J. Am. Chem. Soc. 2007, 129, 3050
30. D. C. Magri, G. J. Brown, G. D. McClenaghan, A. P. de Silva, J. Am. Chem. Soc. 2006, 128, 4950
31. C. Trieflinger, H. Röhr, K. Rurack, J. Daub, Angew. Chem. 2005, 117, 7104
32. Angew. Chem. Int. Ed. 2005, 44, 6943
33. A. Petitjean, N. Kyristsakas, J. M. Lehn, Chem. Eur. J. 2005, 11, 6818
34. D. Ú. Leigh, M. A. F. Morales, E. M. Pérez, J. K. Y. Wong, C. G. Saiz, A. M. Z. Slawin, A. J. Carmichael, D. M. Haddleton, A. M. Brouwer, W. J. Buma, G. W. H. Wurpel, S. Lean, F. Zerbetto, Angew. Chem. 2005, 117, 3122
35. Angew. Chem. Int. Ed. 2005, 44, 3062
36. B. Bag, P. K. Bharadwaj, Chem. Commun. 2005, 513
37. Y. Zhou, D. Zhang, Y. Zhang, Y. Tang, D. Zhu, J. Org. Chem. 2005, 70, 6164
38. N. Kaur, N. Singh, D. Cairns, J. F. Callan, Org. Lett. 2009, 11, 2229
39. A. F. Li, Y. B. Ruan, Q. Q. Jiang, W. B. He, Y.-B. Jiang, Chem. Eur. J. 2010, 16, 5794.
40. For combinatorial logic operations, see
41. M. de Sousa, B. de Castro, S. Abad, M. A. Miranda, U. Pischel, Chem. Commun. 2006, 2051
42. M. Amelia, M. Baroncini, A. Credi, Angew. Chem. 2008, 120, 6336
43. Angew. Chem. Int. Ed. 2008, 47, 6240
44. U. Pischel, B. Heller, New J. Chem. 2008, 32, 395
45. Y. Shiraishi, Y. Tokitoh, T. Hirai, Chem. Commun. 2005, 5316
46. J. M. Montenegro, E. Perez-Inestrosa, D. Collado, Y. Vida, R. Suau, Org. Lett. 2004, 6, 2353
47. K. Szacilowski, Chem. Eur. J. 2004, 10, 2520
48. S. Banthia, A. Samantha, Eur. J. Org. Chem. 2005, 4967
49. M. Suresh, D. A. Jose, A. Das, Org. Lett. 2007, 9, 441
50. M. Kumar, A. Dhir, V. Bhalla, Org. Lett. 2009, 11, 2567
51. G. Zong, G. Lu, J. Phys. Chem. C 2009, 113, 2541
52. S. J. Dickson, A. N. Swinburne, M. J. Paterson, G. O. Lloyd, A. Beeby, J. W. Steed, Eur. J. Inorg. Chem. 2009, 3879
53. K.-C. Chang, I.-H. Su, Y.-Y. Wang, W.-S. Chung, Eur. J. Org. Chem. 2010, 4700
54. M. Yuan, W. Zhou, X. Liu, M. Zhu, J. Li, X. Yin, H. Zheng, Z. Zuo, C. Ouyang, H. Liu, Y. Li, D. Zhu, J. Org. Chem. 2008, 73, 5008.
55. For DNA-based logic operations, see
56. X. Chen, Y. Wang, Q. Liu, Z. Zhang, C. Fan, L. He, Angew. Chem. 2006, 118, 1791
57. Angew. Chem. Int. Ed. 2006, 45, 1759
58. D. Miyoshi, M. Inoue, N. Sugimoto, Angew. Chem. 2006, 118, 7880
59. Angew. Chem. Int. Ed. 2006, 45, 7716
60. W. Yoshida, Y. Yokobayashi, Chem. Commun. 2007, 195
61. S. Ogasawara, T. Ami, K. Fujimoto, J. Am. Chem. Soc. 2008, 130, 10050
62. M. N. Stojanović, D. Stefanović, J. Am. Chem. Soc. 2003, 125, 6673
63. A. Saghatelian, N. H. Volcker, K. M. Guckain, V. S. Y. Lin, M. R. Ghadiri, J. Am. Chem. Soc. 2003, 125, 346
64. A. Okamoto, K. Tanaka, I. Saito, J. Am. Chem. Soc. 2004, 126, 9458.
65. For enzyme-based logic operations, see
66. R. Baron, O. Lioubashevski, E. Katz, T. Niazov, I. Willner, Angew. Chem. 2006, 118, 1602
67. Angew. Chem. Int. Ed. 2006, 45, 1572
68. R. J. Amir, M. Popkov, R. A. Lerner, C. F. Barbas III, D. Shabat, Angew. Chem. 2005, 117, 4452
69. Angew. Chem. Int. Ed. 2005, 44, 4378
70. G. Strack, M. Pita, M. Ornatska, E. Kaitz, ChemBioChem 2008, 9, 1260
71. G. Strack, M. Ornatska, M. Pita, E. Katz, J. Am. Chem. Soc. 2008, 130, 4234
72. J. Zhou, T. K. Tam, M. Pita, M. Ornatska, S. Minko, E. Katz, ACS Appl. Mater. Interfaces 2009, 1, 149
73. I. Tokarev, V. Gopishetty, J. Zhou, M. Pita, M. Motornov, E. Katz, S. Minko, ACS Appl. Mater. Interfaces 2009, 1, 532.
74. C. Kaes, A. Katz, M. W. Hosseini, Chem. Rev. 2000, 100, 3553
75. B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12
76. K. P. Divya, S. Sreejith, C. H. Suresh, A. Ajayaghosh, Chem. Commun. 2010, 46, 8392.
77. G. McSkimming, J. H. R. Tucker, H. Bouas-Laurent, J. P. Desvergne, Angew. Chem. 2000, 112, 2251
78. Angew. Chem. Int. Ed. 2000, 39, 2167
79. A. P. De Silva, I. M. Dixon, H. Q. N. Gunaratne, T. Gunnalaugsson, P. R. S. Maxwell, T. E. Rice, J. Am. Chem. Soc. 1999, 121, 1393.
80. V. Balzani, A. Credi, M. Venturi, ChemPhysChem 2003, 4, 49
81. V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines, Wiley-VCH, Weinheim, 2003
82. A. P. de Silva, N. D. McClenaghan, Chem. Eur. J. 2004, 10, 574
83. F. M. Raymo, Adv. Mater. 2002, 14, 401
84. A. P. de Silva, S. Uchiyama, T. P. Vance, B. Wannalerse, Coord. Chem. Rev. 2007, 251, 1623
85. G. Jiang, Y. Song, X. Guo, D. Zhang, D. Zhu, Adv. Mater. 2008, 20, 2888.
86. W. Sun, C. Zhou, C. H. Xu, C. J. Fang, C. Zhang, Z. X. Li, C. H. Yan, Chem. Eur. J. 2008, 14, 6342.
87. A. Ajayaghosh, P. Carol, S. Sreejith, J. Am. Chem. Soc. 2005, 127, 14962
88. S. Sreejith, K. P. Divya, A. Ajayaghosh, Chem. Commun. 2008, 2903
89. P. Carol, S. Sreejith, A. Ajayaghosh, Chem. Asian J. 2007, 2, 338.
90. K. P. Divya, S. Sreejith, B. Bugga, P. Jayamurthy, P. Anees, A. Ajayaghosh, Chem. Commun. 2010, 46, 6069.
91. D. A. Bruzewicz, M. Reches, G. M. Whitesides, Anal. Chem. 2008, 80, 3387
92. A. W. Martinez, S. T. Philips, E. Carrilho, S. W. Thomas III, H. Sindi, G. M. Whitesides, Anal. Chem. 2008, 80, 3699
93. A. W. Martinez, S. T. Philips, G. M. Whitesides, Proc. Natl. Acad. Sci. USA 2008, 105, 19606
94. E. M. Fenton, M. R. Mascarenas, G. P. Lõpez, S. S. Sibbett, ACS Appl. Mater. Interfaces 2009, 1, 124.
95. L. Tian, W. Zhang, B. Yang, P. Lu, M. Zhang, D. Lu, Y. Ma, J. Shen, J. Phys. Chem. B 2005, 109, 6944
96. B. Yang, L. Tian, H. Zhang, W. Zhang, H. Xu, Z. Xie, P. Lu, M. Zhang, J. Yu, D. Lu, Y. Ma, J. Shen, J. Phys. Chem. B 2006, 110, 16846.