A unique water-tuning dual-channel fluorescence-enhanced sensor for aluminum ions based on a hybrid ligand from a 1,1′-binaphthyl scaffold and an amino acid

Chemistry - A European Journal

Volumn 16, Issue 34, 2010, Pages 10313-10318

  Ma, Tian Hua ^a   Dong, Ming ^a   Dong, Yu Man ^a   Wang, Ya Wen ^a   Peng, Yu ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Aluminum; Binol derivatives; Chromophores; Cooperative recognition; Dual channel sensor; Fluorescence; Sensors

Indexed keywords

ALUMINUM IONS; BINAPHTHYL; BINOL DERIVATIVES; COOPERATIVE RECOGNITION; DUAL CHANNEL; FLUORESCENT SENSORS; HYBRID LIGAND; MOLECULAR PROBES;

ALUMINUM; AMINO ACIDS; CHROMOPHORES; FLUORESCENCE; ORGANIC ACIDS;

SENSORS;

EID: 77956449632     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001431     Document Type: Article

References (88)

1. a) J. M. Lehn, Science 2002, 295, 2400-2403;
2. b) J. M. Lehn, Proc. Natl. Acad. Sci. USA 2002, 99, 4763-4768;
3. c) E. V. Anslyn, J. Org. Chem. 2007, 72, 687-699:
4. d) G. A. Hembury. V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1-73;
5. e) J. W. Steed, J. L. Atwood, Supramolecular Chemistry, Wiley-VCH, Weinheim, 2009.
6. a) 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, 1515-1566;
7. b) J. P. Desvergne, A. W. Czarnik, Chemosensors for Ion and Molecule Recognition, Kluwer Academic, London, 1997:
8. c) B. Valeur, I. Leray, Coord. Chem. Rev. 2000, 205, 3-40;
9. d) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502-532;
10. Angew. Chem. Int. Ed. 2001, 40, 486-516;
11. e) R. Martínez-Máñez, F. Sancenón, Chem. Rev. 2003. 103, 4419-4476;
12. f) F. Mancin. E. Rampazzo, P. Tecilla, U. Tonellato, Chem. Eur. J. 2006, 12, 1844-1854.
13. J. R. Lakowicz, Topics in Fluorescence Spectroscopy, Vol. 4: Probe Design and Chemical Sensing. Kluwer Academic, New York, 2002.
14. a) J. V. Mello, N. S. Finney, Angew. Chem. 2001, 113, 1584-1586;
15. Angew. Chem. Int. Ed. 2001, 40, 1536-1538;
16. b) K. Choi. A. D. Hamilton. Angew. Chem. 2001. 113, 4030-4033:
17. Angew. Chem. Int. Ed. 2001. 40, 3912-3915;
18. c) A. Caballero, R. Martínez. V. Lloveras. I. Ratera, J. Vidal-Gancedo, K. Wurst, A. Tarraga, P. Molina, J. Veciana, J. Am. Chem. Soc. 2005. 127. 15666-15667.
19. For some recent examples, see: a) R. Martínez. A. Espinosa, A. Tárraga, P. Molina, Org. Lett. 2005. 7. 5869-5872;
20. b) X. Zhang, Y. Xiao, X. Qian. Angew. Chem. 2008, 120. 8145-8149;
21. Angew. Chem. Int. Ed. 2008. 47. 8025-8029:
22. c) Z. Xu. N. J. Singh, J. Lim. J. Pan, H. N. Kim. S. Park. K. S. Kim, J. Yoon. J. Am. Chem. Soc. 2009, 131, 15528-15533;
23. d) Y. Zhou, F. Wang, Y. Kim, S.-J. Kim, J. Yoon, Org. Lett. 2009, 11, 4442-4445;
24. e) W. Lin, L. Yuan. Z. Cao. Y. Feng, J. Song, Angew. Chem. 2010, 122, 385-389;
25. Angew. Chem. Int. Ed. 2010. 49. 375-379.
26. a) G. H. Robinson. Chem. Eng. News 2003, 81, 54;
27. b) E. R. Scerri, The Periodic Table: Its Story and Its Significance, Oxford University Press, Oxford, 2007:
28. c) Special issue on "Aluminium: Lithosphere to Biosphere (and Back)": J. Inorg. Biochem. 2005, 99, 1747-1920.
29. a) D. P. Perl, A. R. Brody, Science 1980, 208. 297-299;
30. b) D. P. Perl, D. C. Gajdusek, R. M. Garruto, R. T. Yanagihara. C. J. Gibbs. Science 1982. 217. 1053-1055.
31. 3+ florescent chemosensors can be found so far, see: a) S. H. Kim, H. S. Choi, J. Kim, S. J. Lee, D. T. Quang, J. S. Kim, Org. Lett. 2010, 12, 560-563;
32. b) Y.-W. Wang, M.-X. Yu, Y.-H. Yu, Z.-P. Bai, Z. Shen, F.-Y. Li, X.-Z. You, Tetrahedron Lett. 2009, 50, 6169-6172;
33. c) J.-Q. Wang, L. Huang, L. Gao, J. H. Zhu, Y. Wang, X. Fan, Z. Zou, Inorg. Chem. Commun. 2008, 11, 203-206;
34. d) W. Lin, L. Yuan, J. Feng, Eur. J. Org. Chem. 2008, 3821-3825;
35. e) J. Ren, H. Tian, Sensors 2007, 7, 3166-3178;
36. f) A. B. Othman, J. W. Lee, Y.-D. Huh, R. Abidi, J. S. Kim, J. Vicens, Tetrahedron 2007, 63, 10793-10800;
37. g) Y. Zhao, Z. Lin, H. Liao, C. Duan, Q. Meng, Inorg. Chem. Commun. 2006, 9, 966-968;
38. h) A. Jeanson, V. Béreau, Inorg. Chem. Commun. 2006, 9, 13-17;
39. i) S. M. Ng, R. Narayanaswamy, Anal. Bioanal. Chem. 2006, 386, 1235-1244;
40. J) J.-B. Mulon, E. Destandau, V. Alain and E. Bardez, J. Inorg. Biochem. 2005, 99, 1749-1755;
41. k) M. Arduini, F. Felluga, F. Mancin, P. Rossi, P. Tecilla, U. Tonellato, N. Valentinuzzi, Chem. Commun. 2003, 1606-1607;
42. l) J. L. Ren, J. Zhang, J. Q. Luo, X. K. Pei, Z. X. Jiang, Analyst 2001, 126, 698-702;
43. m) C. Jiang, B. Tang, R. Wang, J. Yen, Talanta 1997, 44, 197-202;
44. n) L. A. Saari, W. R. Seltz, Anal Chem. 1983, 55, 667-670; for a very recent reference, see:
45. o) D. Maity, T. Govindaraju, Chem. Commun. 2010, 46, 4499-4501.
46. a) G. C. Cotzias, P.S. Papavasiliou, R. Gellene, N. Engl J. Med. 1969, 281, 272;
47. b) for a historic account about evolution of L-DOPA as an efficient remedy of Parkinson's disease, see: A. Carlsson, A Half-century of Neurotransmitter Research: Impact on Neurology and Psychiatry, The Nobel Foundation, Stockholm, 2000, pp. 303-322;
48. c) for a historic account of industrial asymmetric synthesis of LDOPA, see: (Nobel Lecture) W. S. Knowles, Angew. Chem. 2002, 114, 2096-2107;
49. Angew. Chem. Int. Ed. 2002, 41, 1998-2007.
50. 1, 1′ -Binaphthyl fluorophores are very useful in molecular recognition, for a review, see: a) L. Pu, Chem. Rev. 2004, 104, 1687-1716; for selected examples, see:
51. b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347;
52. c) H. L. Liu, X. L. Hou, L. Pu, Angew. Chem. 2009, 121, 388-391;
53. Angew. Chem. Int. Ed. 2009, 48, 382-385;
54. d) H. L. Liu, Q. Peng, Y.-D. Wu, D. Chen, X. L. Hou, M. Sabat, L. Pu, Angew. Chem. 2010, 122, 612-616;
55. Angew. Chem. Int. Ed. 2010, 49, 602-606.
56. A. W. Czarnik, Acc. Chem. Res. 1994, 27, 302-308.
57. a) E. U. Akkaya, M. E. Huston, A. W. Czarnik, J. Am. Chem. Soc. 1990, 112, 3590-3593;
58. b) M.-Y. Chae, J. Yoon, A. W. Czarnik, J. Mol Recognit. 1996, 9, 297-303;
59. c) J. S. Kim, K. H. Noh, S. H. Lee, S. K. Kim, S. K. Kim, J. Yoon, J. Org. Chem. 2003, 68, 597-600;
60. d) L. Xue, Q. Liu, H. Jiang, Org. Lett. 2009, 11, 3454-3457.
61. H. A. Benesi, J. H. Hildebrand, J. Am. Chem. Soc. 1949, 71, 2703-2707.
62. A. Chatterjee, M. Santra, N. Won, S. Kim, J. K. Kim, S. B. Kim, K. H. Ahn, J. Am. Chem. Soc. 2009, 131, 2040-2041.
63. a) Z.-B. Li, J. Lin, L. Pu, Angew. Chem. 2005, 117, 1718-1721;
64. Angew. Chem. Int. Ed. 2005, 44, 1690-1693;
65. b) Z.-B. Li, J. Lin, M. Sabat, M. Hyacinth, L. Pu, J. Org. Chem. 2007, 72, 4905-4916.
66. The previous DCF sensors with two fluorophore always demonstrated enhancement and reduction of fluorescence at two wavelengths respectively, see reference [5b] for details. Note that Lin et al. also observed double amplification with their DCF sensor with two fluorophores; however, the excimer emission band was not prominent, see reference [8d]. An example involving fluorescence enhancement at two emission bands in DCF sensors with one fluorophore can be found in reference [10d].
67. We thank one of the referees for drawing out attention to the effect of concentration, details of which can be found in reference [15b] and Z.-B. Li, J. Lin, H. C. Zhang, M. Sabat, M. Hyacinth, L. Pu, J. Org. Chem. 2004, 69, 6284-6293.
68. a) J. Chin, S. S. Lee, K. J. Lee, S. Park, D. H. Kim, Nature 1999, 401, 254-2257;
69. b) H. Aït-Haddou, S.L. Wishur, V.M. Lynch, E.V. Anslyn, J. Am. Chem. Soc. 2001, 123, 11296-11297;
70. c) N. Shao, J. Y. Jin, S. M. Cheung, R. H. Yang, W. H. Chan, T. Mo, Angew. Chem. 2006, 118, 5066-5070;
71. Angew. Chem. Int. Ed. 2006, 45, 4944-4948.
72. The synergistic hydrogen-bonding interactions from the water molecule play a vital role in a number of systems, for some leading references, see: a) F. H. Stillinger, Science 1980, 209, 451-457;
73. b) A. Luzar, D. Chandler, Nature 1996, 379, 55-57;
74. c) K. Liu, J. D. Cruzan, R. J. Saykally, Science 1996, 271, 929-933;
75. d) L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469-472;
76. e) P. Wernet, D. Nordlund, U. Bergmann, M. Cavalleri, M. Odelius, H. Ogasawara, L. Å. Näslund, T. K. Hirsch, L. Ojamäe, P. Glatzel, L. G. M. Pettersson, A. Nilsson, Science 2004, 304, 995-999;
77. f) J. D. Smith, C. D. Cappa, K. R. Wilson, B. M. Messer, R. C. Cohen, R. J. Saykally, Science 2004, 306, 851-853;
78. g) A. Luzar, Chem. Phys. 2000, 258, 267-276;
79. h) I. Vilotijevic, T. F. Jamison, Science 2007, 317, 1189-1192; for reviews, see :
80. i) G. Gilli, P. Gilli, The Nature of the Hydrogen Bond: Outline of a Comprehensive Hydrogen Bond Theory, Oxford University Press, New York. 2009.
81. The combinatorial construction of libraries of probe candidates has been demonstrated to be a very powerful and a promising approach for discovering novel fluorescent sensors, for selected examples, see: a) A. W. Czarnik, Chem. Biol. 1995, 2, 423-428;
82. b) C. T. Chen, H. Wagner, W. C. Still, Science 1998, 279, 851-853;
83. c) S. E. Schneider, S. N. O'Neil, E. V. Anslyn, J. Am. Chem. Soc. 2000, 122, 542-543;
84. d) J. V. Mello, N. S. Finney, J. Am. Chem. Soc. 2005, 127, 10124-10125;
85. e) H. Sunahara, Y. Urano, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2007, 129, 5597-5604;
86. f) T. Peng, D. Yang, Org. Lett. 2010, 12, 496-499;
87. g) A. Pal, M. Bérubé, D. G. Hall, Angew. Chem. 2010, 122, 1534-1537;
88. Angew. Chem. Int. Ed. 2010, 49, 1492-1495, and references therein.