A pyrrole-based triazolium-phane with NH and cationic CH donor groups as a receptor for tetrahedral oxyanions that functions in polar media

Chemical Science

Volumn 4, Issue 4, 2013, Pages 1560-1567

  Cai, Jiajia ^a   Hay, Benjamin P ^b   Young, Neil J ^b   Yang, Xiaoping ^a   Sessler, Jonathan L ^a,c  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b OAK RIDGE NATIONAL LABORATORY   (United States)

^c Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; BENZENE; CHLORINE COMPOUNDS; ELECTRONIC STRUCTURE; HYDROGEN BONDS; METHANOL; NEGATIVE IONS; ORGANIC SOLVENTS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

CHLORIDE ANIONS; CLICK CHEMISTRY; DONOR GROUPS; ELECTRONIC STRUCTURE CALCULATIONS; H NMR SPECTROSCOPY; HIGH SELECTIVITY; HOST GUEST INTERACTIONS; INTRINSIC STRENGTH; MACROCYCLES; MIXED SALTS; MONOANIONS; OXYANIONS; PHOSPHATE ANIONS; POLAR MEDIA; RECEPTOR-1; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; THEORETICAL CALCULATIONS;

AROMATIC COMPOUNDS;

EID: 84874644019     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc22144j     Document Type: Article

References (77)

1. J.-M. Lehn, Science, 2002, 295, 2400
2. P. de Hoog, P. Gamez, I. Mutikainen, U. Turpeinen, J. Reedijik, Angew. Chem. Int. Ed, 2004, 43, 5815
3. J. L. Sessler, D. Seidel, Angew. Chem. Int. Ed, 2003, 42, 5134
4. P. A. Gale, Coord. Chem. Rev, 2003, 240, 191
5. P. D. Beer, P. A. Gale, Angew. Chem. Int. Ed, 2001, 40, 486
6. P. Schmidtchen, M. Berger, Chem. Rev, 1997, 97, 1609
7. A. Bianchi, K. Bowman-James and E. García-Espãna, Supramolecular Chemistry of Anions, Wiley-VCH, Chichester, New York, 1997
8. J. L. Sessler, P. A. Gale and W.-S. Cho, Anion Receptor Chemistry, RSC Publishing, Cambridge, UK, 2006
9. C. P. Mathews and K. E. van Hold, Biochemistry, The Benjamin/Cummings Publishing Company, Inc., Redwood City, CA, 1990
10. S. Xu, M. He, H. Yu, X. Cai, X. Tan, B. Lu, B. Shu, Anal. Biochem, 2001, 299, 188
11. M. Ronaghi, S. Karamohamed, B. Pettersson, M. Uhlén, P. Nyrén, Anal. Biochem, 1996, 242, 84
12. W. Saenger, Principles of Nucleic Acid Structure, Springer-Verlag, New York, 1988
13. B. A. Moyer, R. Custelcean, B. P. Hay, J. L. Sessler, K. Bowman-James, V. W. Day and S.-O. Kang, Inorg. Chem., ASAP; doi: 10.1021/ic3016832
14. J. L. Sessler, S.-K. Kim, D. E. Gross, C.-H. Lee, J.-S. Kim, V. M. Lynch, J. Am. Chem. Soc. 2008, 130, 13162
15. S.-O. Kang, D. Powell, V. W. Day, K. Bowman-James, Angew. Chem. Int. Ed, 2006, 45, 1921
16. C. R. Bondy, P. A. Gale, S. J. Loeb, J. Am. Chem. Soc. 2004, 126, 5030
17. S. L. Tobey, E. V. Anslyn, J. Am. Chem. Soc. 2003, 125, 14807
18. J. L. Sessler, J. Cai, H.-Y. Gong, X. Yang, J. F. Arambula, B. P. Hay, J. Am. Chem. Soc. 2010, 132, 14058
19. K. Mullen, J. Mercurio, C. Serpell, P. D. Beer, Angew. Chem. Int. Ed, 2009, 48, 4781
20. D. W. Yoon, D. E. Gross, V. M. Lynch, J. L. Sessler, B. P. Hay, C.-H. Lee, Angew. Chem. Int. Ed, 2008, 47, 5038
21. Y. Li, A. H. Flood, Angew. Chem. Int. Ed, 2008, 47, 2649
22. V. S. Bryantsev, B. P. Hay, J. Am. Chem. Soc. 2005, 127, 8282
23. K. Chellappan, N. J. Singh, I.-C. Hwang, J. W. Lee, K. S. Kim, Angew. Chem. Int. Ed, 2005, 44, 2899
24. S. Lee, Y. Hua, H. Park, A. H. Flood, Org. Lett, 2010, 12, 2100
25. M. Yano, C. C. Tong, M. E. Light, F. P. Schmidtchen, P. A. Gale, Org. Biomol. Chem. 2010, 8, 4356
26. Y. Hua, A. H. Flood, J. Am. Chem. Soc. 2010, 132, 12838
27. Y. Hua, A. H. Flood, Chem. Soc. Rev, 2010, 39, 1262
28. T. Romero, A. Caballero, A. Tárraga, P. Molina, Org. Lett, 2009, 11, 3466
29. H. Juwarker, J. M. Lenhardt, J. C. Castillo, S. L. Craig, J. Org. Chem. 2009, 74, 8924
30. M. G. Fisher, P. A. Gale, J. R. Hiscock, M. B. Hursthouse, M. E. Light, F. P. Schmidtchen, C. C. Tong, Chem. Commun, 2009, 3017
31. Y. Li, M. Pink, J. A. Karty, A. H. Flood, J. Am. Chem. Soc. 2008, 130, 17293
32. H. Juwarker, J. M. Lenhardt, D. M. Pham, S. L. Craig, Angew. Chem. Int. Ed, 2008, 47, 3740
33. R. M. Meudtner, S. Hecht, Angew. Chem. Int. Ed, 2008, 47, 4926
34. B. K. Keitz, J. Bouffard, G. Bertrand, R. H. Grubbs, J. Am. Chem. Soc. 2011, 133, 8498
35. J. Bouffard, B. K. Keitz, R. Tonner, G. Guisado-Barrios, G. Frenking, R. H. Grubbs, G. Bertrand, Organometallics, 2011, 30, 2617
36. J. Cai, X. Yang, K. Arumugam, C. W. Bielawski, J. L. Sessler, Organometallics, 2011, 30, 5033
37. R. Saravanakumar, V. Ramkumar, S. Sankararaman, Organometallics, 2011, 30, 1689
38. A. Prades, E. Peris, M. Albrecht, Organometallics, 2011, 30, 1162
39. K. Ohmatsu, M. Kiyokawa, T. Ooi, J. Am. Chem. Soc. 2011, 133, 1307
40. G. T. Spence, M. B. Pitak, P. D. Beer, Chem–Eur. J, 2012, 18, 7100
41. L. C. Gilday, N. G. White, P. D. Beer, Dalton Trans, 2012, 41, 7092
42. N. G. White, S. Carvalho, V. Felix, P. D. Beer, Org. Biomol. Chem. 2012, 10, 6951
43. N. G. White, P. D. Beer, Beilstein J. Org. Chem. 2012, 8, 246
44. R. K. Chhatra, A. Kumar, P. S. Pandey, J. Org. Chem. 2011, 76, 9086
45. N. L. Kilah, M. D. Wise, C. J. Serpell, A. L. Thompson, N. G. White, K. E. Christensen, P. D. Beer, J. Am. Chem. Soc. 2010, 132, 11893
46. B. Schulze, C. Friebe, M. D. Hager, W. Guenther, U. Koehn, B. O. Jahn, H. Goerls, U. S. Schubert, Org. Lett, 2010, 12, 2710
47. A. Kumar, P. S. Pandey, Org. Lett, 2008, 10, 165
48. C. W. Tornøe, M. Meldal, Chem. Rev, 2008, 108, 2952
49. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed, 2001, 40, 2004
50. J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev, 2007, 36, 1249
51. D. Fournier, R. Hoogenboom, U. S. Schubert, Chem. Soc. Rev, 2007, 36, 1369
52. J. F. Lutz, Angew. Chem. Int. Ed, 2007, 46, 1018
53. V. Ladmiral, G. Mantovani, G. J. Clarkson, S. Cauet, J. L. Irwin, D. M. Haddleton, J. Am. Chem. Soc. 2006, 128, 4823
54. D. D. Diaz, K. Rajagopal, E. Strable, J. Schneider, M. G. Finn, J. Am. Chem. Soc. 2006, 128, 6056
55. M. Whiting, J. C. Tripp, Y.-C. Lin, W. Lindstrom, A. J. Olson, J. H. Elder, K. B. Sharpless, V. V. Fokin, J. Med. Chem. 2006, 49, 7697
56. S. Punna, J. Kuzelka, Q. Wang, M. G. Finn, Angew. Chem. Int. Ed, 2005, 44, 2215
57. K. D. Bodine, D. Y. Gin, M. S. Gin, J. Am. Chem. Soc. 2004, 126, 1638
58. P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Frechet, K. B. Sharpless, V. V. Fokin, Angew. Chem. Int. Ed, 2004, 43, 3928
59. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192
60. A. J. Link, D. A. Tirrell, J. Am. Chem. Soc. 2003, 125, 11164
61. H. C. Kolb, K. B. Sharpless, Drug Discovery Today, 2003, 8, 1128
62. N. J. Tom, W. M. Simon, H. N. Frost, M. Ewing, Tetrahedron Lett, 2004, 45, 905
63. S. K. Kim, J. L. Sessler, D. E. Gross, C.-H. Lee, J. S. Kim, V. M. Lynch, L. H. Delmau, B. P. Hay, J. Am. Chem. Soc. 2010, 132, 5827
64. J. Bourson, J. Pouget, B. Valeur, J. Phys. Chem. 1993, 97, 4552
65. S. Otto, S. Kubik, J. Am. Chem. Soc. 2003, 125, 7804
66. S. Kubik, R. Goddard, Proc. Natl. Acad. Sci. U. S. A, 2002, 99, 5127
67. S. Kubik, R. Kirchner, D. Nolting, J. Seidel, J. Am. Chem. Soc. 2002, 124, 12752
68. S. Kubik, R. Goddard, R. Kirchner, D. Nolting, J. Seidel, Angew. Chem. Int. Ed, 2001, 40, 2648
69. P. Mateus, R. Delgado, P. Brandão, V. Félix, J. Org. Chem. 2009, 74, 8638
70. P. Mateus, R. Delgado, P. Brandão, S. Carvalho, V. Félix, Org. Biomol. Chem. 2009, 7, 4661
71. B. Dietrich, D. L. Fyles, T. M. Fyles, J.-M. Lehn, Helv. Chim. Acta, 1979, 62, 2763
72. R. A. Kendall, E. Apra, D. E. Bernholdt, E. J. Bylaska, M. Dupuis, G. I. Fann, R. J. Harrison, J. L. Ju, J. A. Nichols, J. Nieplocha, T. P. Straatsma, T. L. Windus, A. T. Wong, Comput. Phys. Commun, 2000, 128, 260
73. M. Valiev, E. J. Bylaska, N. Govind, K. Kowalski, T. P. Straatsma, H. J. J. Van Dam, D. Wang, J. Nieplocha, E. Apra, T. L. Windus, W. de Jong, Comput. Phys. Commun, 2010, 181, 1477
74. A. V. Marenich, R. M. Olson, C. P. Kelly, C. J. Cramer, D. G. Truhlar, J. Chem. Theory Comput, 2007, 3, 2011
75. Spartan 10, Wavefunction, Inc., Irvine, California 92612
76. B. P. Hay, T. K. Firman, B. A. Moyer, J. Am. Chem. Soc. 2005, 109, 832
77. V. S. Bryantsev, B. P. Hay, Org. Lett, 2005, 7, 5031