First supramolecular sensors for phosphonate anions

Chemical Science

Volumn 4, Issue 9, 2013, Pages 3617-3623

  Esipenko, Nina A ^a   Koutnik, Petr ^a   Minami, Tsuyoshi ^a   Mosca, Lorenzo ^a   Lynch, Vincent M ^b   Zyryanov, Grigory V ^a   Anzenbacher, Pavel ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION BINDING; ANION SENSORS; FLUORESCENCE SIGNAL AMPLIFICATION; HIGH-THROUGHPUT SCREENING; HYDROLYSIS PRODUCTS; PHOSPHATE ANIONS; PHOSPHONATES; SUPRAMOLECULAR SENSORS;

CHEMICAL SENSORS; NEGATIVE IONS;

FLUORESCENCE;

EID: 84885622942     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc51407b     Document Type: Article

References (102)

1. Calcium and Phosphorus in Health and Disease (Modern Nutrition), ed. J. J. B. Anderson and S. C. Garner, CRC Press, Boca Raton, 1995
2. F. Bronner and M. Peterlik, Extra- and Intracellular Calcium and Phosphate Regulation: From Basic Research to Clinical Medicine, CRC Press, Boca Raton, 1992
3. R. A. Molins, Phosphates in Food, CRC Press, Boca Raton, 1990
4. S. A. Parsons and B. Jefferson, Introduction to Potable Water Treatment Processes, Blackwell Publishing, Oxford, 2006
5. N. F. Gray, Drinking Water Quality: Problems and Solutions, Cambridge University Press, Cambridge, 2nd edn, 2008
6. Phosphorus and Nitrogen Removal from Municipal Wastewater: Principles and Practice, ed. R. I. Sedlak, Lewis Publishers-CRC Press, Boca Raton, 2nd edn, 1991
7. F. Ullman, Ullmann's Encyclopedia of Industrial Chemistry, Wiley VCH, New York, 6th edn, 1999
8. F. T. Nielsson, Manual of Fertilizer processing, Marcel Dekker, New York, 1987
9. Environmental Impact of Fertilizer on Soil and Water, ed. W. L. Hall, Jr, W. P. Robarge, ACS Symposium Series, vol. 872, 2003
10. M. Sierra Pollution Control in Fertilizer Production Environ. Sci. Pollut. Control Ser. 1994 10: 145
11. B. Nowack: Water Res. 2003 37: 2533-2546
12. E. V. Giger, B. Castagner, J. C. Leroux: J. Controlled Release 2013 167: 175-188
13. M. McClung, S. T. Harris, P. D. Miller, D. C. Bauer, K. S. Davison, L. Dian, D. A. Hanley, D. L. Kendler, C. K. Yuen, E. M. Lewiecki: Am. J. Med. 2013 126: 13-20
14. E. De Clercq: Biochem. Pharmacol. 2011 82: 99-109
15. C. Callebaut, K. Stray, L. Tsai, M. Williams, Z. Y. Yang, C. Cannizzaro, S. A. Leavitt, X. Liu, K. Wang, B. P. Murray, A. Mulato, M. Hatada, T. Priskich, N. Parkin, S. Swaminathan, W. Lee, G. X. He, L. Xu, T. Cihlar: Antimicrob. Agents Chemother. 2011 55: 1366-1376
16. E. De Clercq: Biochem. Pharmacol. 2007 73: 911-922
17. E. De Clercq: Clin. Microbiol. Rev. 2003 16: 569-596
18. C. C. Green, S. E. Lochmann, D. L. Straus: J. Toxicol. Environ. Health, Part A 2005 68: 141-149
19. F. C. Hoskin: Can. J. Biochem. Physiol. 1956 34: 75-79
20. Chemical Warfare Agent: Chemistry, Pharmacology, Toxicology, and Therapeutics, ed. J. A. Romano, Jr, B. J. Lukey and H. Salem, CRC Press, 2007
21. H. S. Hewage, K. J. Wallace, E. V. Anslyn: Chem. Commun. 2007 3909-3911
22. A. M. Costero, S. Gil, M. Parra, P. M. E. Mancini, R. Martínez-Máñez, F. Sancenón, S. Royob: Chem. Commun. 2008 6002-6004
23. M. R. Sambrook, J. R. Hiscock, A. Cook, A. C. Green, I. Holden, J. C. Vincent, P. A. Gale: Chem. Commun. 2012 48: 5605-5607
24. F. Wang, H. Gu, T. M. Swager: J. Am. Chem. Soc. 2008 130: 5392-5393
25. T. J. Dale, J. Rebek, Jr: J. Am. Chem. Soc. 2006 128: 4500-4501
26. S. Bencic-Nagale, T. Sternfeld, D. R. Walt: J. Am. Chem. Soc. 2006 128: 5041-5048
27. C. Tudisco, P. Betti, A. Motta, R. Pinalli, L. Bombaci, E. Dalcanale, G. G. Condorelli: Langmuir 2012 28: 1782-1789
28. U. V. Saradhi, S. Prabhakar, T. J. Reddy, M. Vairamani: J. Chromatogr., A 2006 1129: 9-13
29. R. A. Evans, E. M. Jakubowski, W. T. Muse, K. Matson, S. W. Hulet, R. J. Mioduszewski, S. A. Thomson, A. L. Totura, J. A. Renner, C. L. Crouse: J. Anal. Toxicol. 2008 32: 78-85
30. M. Kataoka, Y. Seto: J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2003 795: 123-132
31. P. Kubáň, A. Seiman, N. Makarõtševa, M. Vaher, M. Kaljurand: J. Chromatogr., A 2011 1218: 2618-2625
32. V. Tak, D. Pardasani, P. K. Kanaujia, D. K. Dubey: J. Chromatogr., A 2009 1216: 4319-4328
33. T. R. Crompton, Determination of anions in natural and treated waters, SPON Press, London, 2002
34. J. L. Sessler, P. A. Gale and W. Cho, in Anion Receptor Chemistry; Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge, 2006
35. R. Martínez-Máñez, F. Sancenón: Chem. Rev. 2003 103: 4419-4476
36. P. D. Beer, P. A. Gale: Angew. Chem., Int. Ed. 2001 40: 486-516
37. F. P. Schmidtchen, M. Berger: Chem. Rev. 1997 97: 1609-1646
38. V. Amendola, M. Boiocchi, D. Esteban-Gomez, L. Fabbrizzi, E. Monzani: Org. Biomol. Chem. 2005 3: 2632-2639
39. M. Boiocchi, L. Fabbrizzi, M. Garolfi, M. Licchelli, L. Mosca, C. Zanini: Chem.-Eur. J. 2009 15: 11288-11297
40. Y. Kubo, T. Ishida, T. Minami, T. D. James: Chem. Lett. 2006 35: 996-997
41. T. Minami, K. Kaneko, T. Nagasaki, Y. Kubo: Tetrahedron Lett. 2008 49: 432-436
42. A. Nonaka, S. Horie, T. D. James, Y. Kubo: Org. Biomol. Chem. 2008 6: 3621-3625
43. T. Minami, Y. Kubo: Chem.-Asian J. 2010 5: 605-611
44. T. Nishimura, S.-Y. Xu, Y.-B. Jiang, J. S. Fossey, K. Sakurai, S. D. Bull, T. D. James: Chem. Commun. 2013 49: 478-480
45. J. W. Steed: Chem. Soc. Rev. 2009 38: 506-519
46. D. R. Turner, M. J. Paterson, J. W. Steed: J. Org. Chem. 2006 71: 1598-1608
47. C. A. Ilioudis, D. A. Tocher, J. W. Steed: J. Am. Chem. Soc. 2004 126: 12395-12402
48. P. A. Gale, C. C. Tong, C. J. E. Haynes, O. Adeosun, D. E. Gross, E. Karnas, E. M. Sedenberg, R. Quesada, J. L. Sessler: J. Am. Chem. Soc. 2010 132: 3240-3241
49. C. Bejger, J. S. Park, E. S. Silver, J. L. Sessler: Chem. Commun. 2010 46: 7745-7747
50. A. E. Hargrove, S. Nieto, T. Zhang, J. L. Sessler, E. V. Anslyn: Chem. Rev. 2011 111: 6603-6782
51. P. Sokkalingam, D. S. Kim, H. Hwang, J. L. Sessler, C.-H. Lee: Chem. Sci. 2012 3: 1819-1824
52. R. M. Duke, E. B. Veale, F. M. Pfeffer, P. E. Kruger, T. Gunnlaugsson: Chem. Soc. Rev. 2010 39: 3936-3953
53. E. Quinlan, S. E. Matthews, T. Gunnlaugsson: J. Org. Chem. 2007 72: 7497-7503
54. M. Wenzel, J. R. Hiscock, P. A. Gale: Chem. Soc. Rev. 2012 41: 480-520
55. H. T. Ngo, X. Liu, K. A. Jolliffe: Chem. Soc. Rev. 2012 41: 4928-4965
56. S. R. Bayly, P. D. Beer: Struct. Bonding 2008 129: 45-94
57. R. M. Duke, T. Gunnlaugsson: Tetrahedron Lett. 2011 52: 1503-1505
58. M. A. Palacios, R. Nishiyabu, M. Marquez, P. Anzenbacher, Jr: J. Am. Chem. Soc. 2007 129: 7538-7544
59. R. Nishiyabu, M. A. Palacios, W. Dehaen, P. Anzenbacher, Jr: J. Am. Chem. Soc. 2006 128: 11496-11504
60. R. Nishiyabu, P. Anzenbacher, Jr: Org. Lett. 2006 8: 359-362
61. R. Nishiyabu, P. Anzenbacher, Jr: J. Am. Chem. Soc. 2005 127: 8270-8271
62. P. Anzenbacher, Jr, M. A. Palacios, K. Jursíková, M. Marquez: Org. Lett. 2005 7: 5027-5030
63. D. Aldakov, M. A. Palacios, P. Anzenbacher, Jr: Chem. Mater. 2005 17: 5238-5241
64. D. Aldakov, P. Anzenbacher, Jr: J. Am. Chem. Soc. 2004 126: 4752-4753
65. P. Anzenbacher, Jr, K. Jursíková, D. Aldakov, M. Marquez, R. Pohl: Tetrahedron 2004 60: 11163-11168
66. Y.-L. Liu, M. A. Palacios, P. Anzenbacher, Jr: Chem. Commun. 2010 1860-1862
67. Z. Wang, M. A. Palacios, P. Anzenbacher, Jr: Anal. Chem. 2008 80: 7451-7459
68. M. A. Palacios, Z. Wang, V. A. Montes, G. V. Zyryanov, P. Anzenbacher, Jr: J. Am. Chem. Soc. 2008 130: 10307-10314
69. Z. Wang, M. A. Palacios, G. Zyryanov, P. Anzenbacher, Jr: Chem.-Eur. J. 2008 14: 8540-8546
70. G. V. Zyryanov, M. A. Palacios, P. Anzenbacher, Jr: Org. Lett. 2008 10: 3681-3684
71. G. V. Zyryanov, M. A. Palacios, P. Anzenbacher, Jr: Angew. Chem., Int. Ed. 2007 46: 7849-7852
72. M. A. Palacios, Z. Wang, V. A. Montes, G. V. Zyryanov, B. J. Hausch, K. Jursíková, P. Anzenbacher, Jr: Chem. Commun. 2007 3708-3710
73. R. Pohl, D. Aldakov, P. Kubát, K. Jursíková, M. Marquez, P. Anzenbacher, Jr: Chem. Commun. 2004 1282-1283
74. D. Aldakov, P. Anzenbacher, Jr: Chem. Commun. 2003 1394-1395
75. P. Anzenbacher, Jr, D. S. Tyson, K. Jursíková, F. N. Castellano C: J. Am. Chem. Soc. 2002 124: 6232-6233
76. T. Minami, N. A. Esipenko, B. Zhang, M. E. Kozelkova, L. Isaacs, R. Nishivabu, Y. Kubo, P. Anzenbacher, Jr: J. Am. Chem. Soc. 2012 134: 20021-20024
77. P. Anzenbacher, Jr, L. Mosca, M. A. Palacios, G. V. Zyryanov, P. Koutnik: Chem.-Eur. J. 2012 18: 12712-12718
78. D. Lucas, T. Minami, G. Iannuzzi, L. Cao, J. B. Wittenberg, P. Anzenbacher, Jr, L. Isaacs: J. Am. Chem. Soc. 2011 133: 17966-17976
79. T. D. P. Stack, Z. Hou, K. N. Raymond: J. Am. Chem. Soc. 1993 115: 6466-6467
80. K. J. Wallace, R. Hanes, E. Anslyn, J. Morey, K. V. Kilway, J. Siegel: Synthesis 2005 2080-2083
81. C. Nativi, M. Cacciarini, O. Francesconi, A. Vacca, G. Moneti, A. Ienco, S. J. Roelens: J. Am. Chem. Soc. 2007 129: 4377-4385
82. V. Amendola, M. Boiocchi, L. Fabbrizzi, A. Palchetti: Chem.-Eur. J. 2005 11: 5648-5660
83. C. Schmuck, M. Schwegmann: J. Am. Chem. Soc. 2005 127: 3373-3379
84. M. Mazik, W. Radunz, R. Boese: J. Org. Chem. 2004 69: 7448-7462
85. D. R. Turner, M. J. Paterson, J. W. Steed: Org. Chem. 2006 71: 1598-1608
86. S. Sasaki, D. Citterio, S. Ozawa, K. J. Suzuki: J. Chem. Soc., Perkin Trans. 2 2001 2309-2313
87. B. T. Nguyen, S. L. Wiskur, E. V. Anslyn: Org. Lett. 2004 6: 2499-2501
88. S. L. Wiskur, P. N. Floriano, E. V. Anslyn, J. T. McDevitt: Angew. Chem., Int. Ed. 2003 42: 2070-2072
89. S. C. McCleskey, A. Metzger, C. S. Simmons, E. V. Anslyn: Tetrahedron 2002 58: 621-628
90. S. L. Wiskur, E. V. Anslyn: J. Am. Chem. Soc. 2001 123: 10109-10110
91. J. L. Lavigne, E. V. Anslyn: Angew. Chem., Int. Ed. 1999 38: 3666-3669
92. A. Metzger, E. V. Anslyn: Angew. Chem., Int. Ed.1998 37: 649-652
93. Y. Bai, B.-G. Zhang, J. Xu, C.-Y. Duan, D.-B. Dang, D.-J. Liu, Q.-J. Meng: New J. Chem. 2005 29: 777-779
94. S. Yun, H. Ihm, H. G. Kim, C.-W. Lee, B. Indrajit, K. S. Oh, Y. J. Gong, J. W. Lee, J. Yoon, H. C. Lee, K. S. Kim: J. Org. Chem. 2003 68: 2467-2470
95. H. Ihm, S. Yun, H. G. Kim, J. K. Kim, K. S. Kim: Org. Lett. 2002 4: 2897-2900
96. B. Kuswandi, Nuriman, W. Verboom, D. N. Reinhoudt: Sensors 2006 6: 978-1017
97. A. Lieben: Ann. Chim. 1870 7: 218
98. R. C. Fusson, B. A. Bull: Chem. Rev. 1934 15: 275-309
99. V. Amendola, M. Boiocchi, L. Fabbrizzi, A. Palchetti: Chem.-Eur. J. 2004 11: 120-127
100. P. A. D'Agostino, J. R. Hancock, L. R. Provost: J. Chromatogr., A 2001 912: 291-299
101. K. R. Beebe, R. J. Pell and M. B. Seasholtz, Chemometrics. A Practical Guide, Wiley & Sons, New York, 1998
102. Lock and Key Principle. The State of the Art100 Years, ed. J.-P. Behr, Perspectives in Supramolecular Chemistry, Wiley, Chichester, 1995