Host-guest chemistry of a water-soluble pillar[5]arene: Evidence for an ionic-exchange recognition process and different complexation modes

Chemistry - A European Journal

Volumn 20, Issue 38, 2014, Pages 12123-12132

  Gõmez, Borja ^a   Francisco, Vitor ^a   Fernández Nieto, Fernando ^a   Garcia Rio, Luis ^a   Martin Pastor M ^b   Paleo, M Rita ^a   Sardina, F Javier ^a  

^a s n   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

calorimetry; host guest systems; ion exchange; molecular recognition; NMR spectroscopy; supramolecular chemistry

Indexed keywords

CALORIMETERS; CALORIMETRY; IONS; MOLECULAR RECOGNITION; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY;

BINDING CONSTANT; HOST-GUEST SYSTEM; HOSTGUEST CHEMISTRY; ISOTHERMAL TITRATION CALORIMETRY; NEUTRAL CONDITIONS; NMR EXPERIMENTS; RECOGNITION PROCESS; THERMODYNAMIC PARAMETER;

ION EXCHANGE;

EID: 84922645489     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403194     Document Type: Article

References (46)

1. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036.
2. F. Hapiot, S. Tilloy, E. Monflier, Chem. Rev. 2006, 106, 767-781.
3. K. Kim, N. Selvapalam, D. H. Oh, J. Inclusion Phenom. Macrocyclic Chem. 2004, 50, 31-36.
4. T. Ogoshi, S. Kanai, S. Fujinami, T. Yamagishi, J. Am. Chem. Soc. 2008, 130, 5022-5023.
5. M. I. N. Xue, Y. Yang, X. Chi, Z. Zhang, F. Huang, Acc. Chem. Res. 2012, 45, 1294-1308.
6. P. J. Cragg, K. Sharma, Chem. Soc. Rev. 2012, 41, 597-607.
7. T. Ogoshi, T. Yamagishi, Eur. J. Org. Chem. 2013, 2961-2975.
8. N. L. Strutt, R. S. Forgan, J. M. Spruell, Y. Y. Botros, J. F. Stoddart, J. Am. Chem. Soc. 2011, 133, 5668-5671.
9. C. Han, G. Yu, B. Zheng, F. Huang, Org. Lett. 2012, 14, 1712-1715.
10. N. L. Strutt, H. Zhang, M. A. Giesener, J. Lei, J. F. Stoddart, Chem. Commun. 2012, 48, 1647-1649.
11. T. Ogoshi, M. Hashizume, T. Yamagishi, Y. Nakamoto, Chem. Commun. 2010, 46, 3708-3710.
12. G. Yu, X. Zhou, Z. Zhang, C. Han, Z. Mao, C. Gao, F. Huang, J. Am. Chem. Soc. 2012, 134, 19489-19497.
13. C. Li, X. Shu, J. Li, S. Chen, K. Han, M. Xu, B. Hu, Y. Yu, X. Jia, J. Org. Chem. 2011, 76, 8458-8465.
14. X.-B. Hu, L. Chen, W. Si, Y. Yu, J.-L. Hou, Chem. Commun. 2011, 47, 4694-4696.
15. Y. Ma, X. Ji, F. Xiang, X. Chi, C. Han, J. He, Z. Abliz, W. Chen, F. Huang, Chem. Commun. 2011, 47, 12340-12342.
16. P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502-532
17. Angew. Chem. Int. Ed. 2001, 40, 486-516.
18. H. Bakirci, A. L. Koner, W. M. Nau, Chem. Commun. 2005, 5411-5413.
19. J. L. Sessler, D. E. Gross, W.-S. Cho, V. M. Lynch, F. P. Schmidtchen, G. W. Bates, M. E. Light, P. A. Gale, J. Am. Chem. Soc. 2006, 128, 12281-12288.
20. M. Arunachalam, P. Ghosh, Chem. Commun. 2011, 47, 8477-8492.
21. N. Douteau-Guével, A. W. Coleman, J. Morel, N. Morel-Desrosiers, J. Phys. Org. Chem. 1998, 11, 693-696.
22. N. Douteau-Guével, A. W. Coleman, J.-P. Morel, N. Morel-Desrosiers, J. Chem. Soc. Perkin Trans. 2 1999, 629-633.
23. N. Douteau-Guével, F. Perret, A. W. Coleman, J.-P. Morel, N. Morel-Desrosiers, J. Chem. Soc. Perkin Trans. 2 2002, 524-532.
24. H. Buschmann, L. Mutihac, E. Schollmeyer, J. Inclusion Phenom. Macrocyclic Chem. 2003, 46, 133-137.
25. V. Francisco, A. Piñeiro, W. M. Nau, L. García-Río, Chem. Eur. J. 2013, 19, 17809-17820.
26. V. Francisco, N. Basilio, L. García-Río, J. Phys. Chem. B 2012, 116, 5308-5315.
27. C. Li, J. Ma, L. Zhao, Y. Zhang, Y. Yu, X. Shu, J. Li, X. Jia, Chem. Commun. 2013, 49, 1924-1926.
28. Y. Ma, M. Xue, Z. Zhang, X. Chi, F. Huang, Tetrahedron 2013, 69, 4532-4535.
29. T. Ogoshi, S. Tanaka, T. Yamagishi, Y. Nakamoto, Chem. Lett. 2011, 40, 96-98.
30. W. S. Price, Concepts Magn. Reson. 1997, 9, 299-336.
31. Y. Cohen, L. Avram, L. Frish, Angew. Chem. 2005, 117, 524-560
32. Angew. Chem. Int. Ed. 2005, 44, 520-554.
33. G. Arena, S. Gentile, F. G. Gulino, D. Sciotto, C. Sgarlata, Tetrahedron Lett. 2004, 45, 7091-7094.
34. Y. Liu, D.-S. Guo, H.-Y. Zhang, Y.-H. Ma, E.-C. Yang, J. Phys. Chem. B 2006, 110, 3428-3434.
35. D.-S. Guo, L.-H. Wang, Y. Liu, J. Org. Chem. 2007, 72, 7775-7778.
36. G. Arena, A. Casnati, A. Contino, A. Magrì, F. Sansone, D. Sciotto, R. Ungaro, Org. Biomol. Chem. 2006, 4, 243-249.
37. N. Basílio, V. Francisco, L. García-Río, J. Org. Chem. 2012, 77, 10764-10772.
38. M. Mayer, B. Meyer, Angew. Chem. 1999, 111, 1902-1906
39. Angew. Chem. Int. Ed. 1999, 38, 1784-1788.
40. B. Meyer, T. Peters, Angew. Chem. 2003, 115, 890-918
41. Angew. Chem. Int. Ed. 2003, 42, 864-890.
42. J. Zhusheng, Y. Zhongxiu, L. Maili, Anal. Biochem. 2009, 385, 380-382.
43. A. Jerschow, M. Norbert, J. Magn. Reson. 1997, 125, 372-375.
44. D. Wu, A. Chen, C. S. Johnson, J. Magn. Reson. Ser. A 1995, 115, 260-264.
45. W. S. Price, Concepts Magn. Reson. 1998, 10, 197-237.
46. A. C. F. Ribeiro, V. M. M. Lobo, A. J. F. N. Sobral, H. T. F. C. Soares, A. R. J. Leal, M. A. Esteso, Acta Chim. Slov. 2010, 57, 410-414.