Oxo-anion recognition by mono- and bisurea pendant-arm macrocyclic complexes

Inorganic Chemistry

Volumn 54, Issue 1, 2015, Pages 47-58

  Boiocchi, Massimo ^a   Licchelli, Maurizio ^a   Milani, Michele ^a   Poggi, Antonio ^a   Sacchi, Donatella ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ANION; BENZOIC ACID; CARBANILIDE DERIVATIVE; CARBOXYLIC ACID; COORDINATION COMPOUND; COPPER; LIGAND; MACROCYCLIC COMPOUND; PHOSPHATE; SUCCINIC ACID;

CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; KINETICS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

ACETIC ACID; ANIONS; BENZOIC ACID; CARBANILIDES; CARBOXYLIC ACIDS; COORDINATION COMPLEXES; COPPER; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; KINETICS; LIGANDS; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; PHOSPHATES; SUCCINIC ACID; THERMODYNAMICS;

EID: 84920597418     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic501527k     Document Type: Article

References (85)

1. Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VCH: New York, 1997.
2. Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; Royal Society of Chemistry: Cambridge, U.K., 2006.
3. Gale, P. A.; Busschaert, N.; Haynes, C. J. E.; Karagiannidis, L. E.; Kirby, I. L. Chem. Soc. Rev. 2014, 43, 205-241
4. Anion Coordination Chemistry; Bowman-James, K.; Bianchi, A.; García-España, E., Eds.; Wiley-VCH: Weinheim, Germany, 2012.
5. Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262-1271
6. ONeil, E. J.; Smith, B. D. Coord. Chem. Rev. 2006, 250, 3068-3080
7. Kubik, S. In Anion Coordination Chemistry; Bowman-James, K.; Bianchi, A.; García-España, E., Eds.; Wiley-VCH: Weinheim, Germany, 2012; p 363.
8. Lehn, J.-M. Supramolecular Chemistry. Concepts and Perspectives; Wiley-WCH: Weinheim, Germany, 1995.
9. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516
10. Caballero, A.; Zapata, F.; Beer, P. D. Coord. Chem. Rev. 2013, 257, 2434-2455
11. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646
12. Casasus, R.; Aznar, E.; Marcos, M. D.; Martínez-Mañez, R.; Sançenón, F.; Soto, J.; Amorós, P. Angew. Chem., Int. Ed. 2006, 45, 6661-6664
13. Santos-Figueroa, L. E.; Moragues, M. E.; Climent, E.; Agostini, A.; Martínez-Mañez, R.; Sançenón, F. Chem. Soc. Rev. 2013, 42, 3489-3613
14. Gale, P. A.; Gunnlaugsson, T., Guest Eds. Chem. Soc. Rev. 2010, 3581-4008 (themed issue on: Supramolecular chemistry of anionic species).
15. Gale, P. A.; Caltagirone, C. Chem. Soc. Rev. 2014, DOI: 10.1039/c4cs00179f.
16. Anion Sensing, Topics in Current Chemistry; Stibor, I., Ed.; Springer: Berlin, 2005.
17. Snowden, T. S.; Anslyn, E. V. Curr. Opin. Chem. Biol. 1999, 3, 740-746
18. Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972
19. Ghosh, K.; Sarkar, A. R.; Sarkar, T.; Panja, S.; Kar, D. RSC Adv. 2014, 4, 20114-20130
20. Graf, E.; Lehn, J.-M. J. Am. Chem. Soc. 1976, 98, 6403-6405
21. Schmidtchen, F. P. Angew. Chem., Int. Ed. Engl. 1977, 16, 720-721
22. Boiocchi, M.; Del Boca, L.; Esteban Gomez, D.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 126, 16507-16514
23. Bondy, C. R.; Loeb, S. J. Coord. Chem. Rev. 2003, 240, 77-99
24. Choi, K.; Hamilton, A. D. Coord. Chem. Rev. 2003, 240, 101-110
25. Cigaň, M.; Jakusova, K.; Donovalova, J.; Szöcs, V.; Gaplovsky, A. RSC Adv. 2014, 4, 54072-54079
26. Kang, S. O.; Hossain, M. A.; Bowman-James, K. Coord. Chem. Rev. 2006, 250, 3038-3052
27. Blondeau, P.; Segura, M.; Perez-Fernandez, R.; de Mendoza, J. Chem. Soc. Rev. 2007, 36, 198-210
28. García-España, E.; Díaz, P.; Llinares, J. M.; Bianchi, A. Coord. Chem. Rev. 2006, 250, 2952-2986
29. Bazzicalupi, C.; Bencini, A.; Lippolis, V. Chem. Soc. Rev. 2010, 39, 3709-3728
30. Kang, S. O.; Llinares, J. M.; Day, V. W.; Bowman-James, K. Chem. Soc. Rev. 2010, 39, 3980-4003
31. Mateus, P.; Bernier, N.; Delgado, R. Coord. Chem. Rev. 2010, 254, 1726-1747
32. Smith, P. J.; Reddington, M. V.; Wilcox, C. S. Tetrahedron Lett. 1992, 41, 6085-6088
33. Fan, E.; van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369-370
34. Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864
35. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221
36. Kubik, S.; Reyheller, C.; Stüwe, S. J. Inclusion Phenom. Macrocyclic Chem. 2005, 52, 137-187
37. Esteban Gómez, D.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. Org. Biomol. Chem. 2005, 1495-1500
38. Esteban-Gómez, D.; Fabbrizzi, L.; Licchelli, M.; Sacchi, D. J. Mater. Chem. 2005, 15, 2670-2675
39. Lin, Y.-S.; Tu, G.-M.; Lin, C.-Y.; Chang, Y.-T.; Yen, Y.-P. New J. Chem. 2009, 33, 860-867
40. Fang, A.-I.; Wang, J.-H.; Wang, F.; Jiang, Y.-B. Chem. Soc. Rev. 2010, 39, 3729-3745
41. Santos-Figueroa, L. E.; Moragues, M. E.; M. Raposo, M. M.; Batista, R. M. F.; Ferreira, R. C. M.; Costa, S. P. G.; Sancenón, F.; Martínez-Máñez, R.; Soto, J.; Ros-Lis, J. V. Tetrahedron 2012, 68, 7179-7176
42. Mercer, D. J.; Stephen J. Loeb, S. J. Chem. Soc. Rev. 2010, 39, 3612-3620
43. Steed, J. W. Chem. Soc. Rev. 2009, 38, 506-519
44. Rice, C. R. Coord. Chem. Rev. 2006, 250, 3190-3199
45. Amendola, V.; Boiocchi, M.; Colasson, B.; Fabbrizzi, L.; Rodriguez Douton, M.-J.; Ugozzoli, F. Angew. Chem., Int. Ed. 2006, 118, 7074-7078
46. Amendola, V.; Boiocchi, M.; Colasson, B.; Fabbrizzi, L. Inorg. Chem. 2006, 45, 6138-6147
47. Amendola, V.; Boiocchi, M.; Colasson, B.; Fabbrizzi, L.; Monzani, E.; Douton-Rodriguez, M.-J.; Spadini, C. Inorg. Chem. 2008, 47, 4808-4816
48. Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 2013, 42, 1681-1699
49. Fabbrizzi, L.; Licchelli, M.; Parodi, L.; Poggi, A.; Taglietti, A. J. Fluoresc. 1998, 8, 263-271
50. Fabbrizzi, L.; Faravelli, I.; Francese, G.; Licchelli, M.; Perotti, A.; Taglietti, A. Chem. Commun. 1998, 971-972
51. Fabbrizzi, L.; Licchelli, M.; Perotti, A.; Poggi, A.; Rabaioli, G.; Sacchi, D.; Taglietti, A. J. Chem. Soc., Perkin Trans. 2 2001, 2108-2113
52. Bergamaschi, G.; Boiocchi, M.; Perrone, M. L.; Poggi, A.; Viviani, I.; Amendola, V. Dalton Trans. 2014, 43, 11352-11360
53. Ngo, H. T.; Liu, X.; Jolliffe, K. A. Chem. Soc. Rev. 2012, 41, 4928-4965
54. Butler, S. J.; Parker, D. Chem. Soc. Rev. 2013, 42, 1652-1666
55. Cabbiness, D. K.; Margerum, D. W. J. Am. Chem. Soc. 1969, 91, 6540-6541
56. Cabbiness, D. K.; Margerum, D. W. J. Am. Chem. Soc. 1970, 92, 2151-2153
57. Fabbrizzi, L.; Licchelli, M.; Mosca, L.; Poggi, A. Coord. Chem. Rev. 2010, 254, 1628-1636
58. dos Santos, C. M. G.; Barrio Fernández, P.; Plush, S. E.; Leonard, J. P.; Gunnlaugsson, T. Chem. Commun. 2007, 3389-3391
59. Amendola, V.; Esteban-Gomez, D.; Fabbrizzi, L.; Licchelli, M.; Monzani, E.; Sançenon, F. Inorg. Chem. 2005, 44, 8690-8698
60. Carreira-Barral, I.; Rodríguez-Blas, T.; Platas-Iglesias, C.; de Blas, A.; Esteban-Gomez, D. Inorg. Chem. 2014, 53, 2554-2568
61. Boiocchi, M.; Fabbrizzi, L.; Garolfi, M.; Licchelli, M.; Mosca, L.; Zanini, C. Chem.-Eur. J. 2009, 15, 11288-11297
62. Licchelli, M.; Milani, M.; Pizzo, S.; Poggi, A.; Sacchi, D.; Boiocchi, M. Inorg. Chim. Acta 2012, 384, 210-218
63. Krapcho, A. P.; Kuell, C. S. Synth. Commun. 1990, 20, 2559-2564
64. He, Y.; Kou, H.-Z.; Li, Y.; Zou, B. C.; Xiong, M.; Li, Y. Inorg. Chem. Commun. 2003, 6, 38-42
65. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753
66. http://www.hyperquad.co.uk/index.htm, accessed April 30, 2014.
67. Wilcox, C. S. Frontiers in Supramolecular Chemistry and Photochemistry; VCH: Weinheim, Germany, 1991; pp 123-143.
68. Wolsey, W. C. J. Chem. Educ. 1973, 50, A335-A337
69. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838
70. North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Crystallogr. 1968, A24, 351-359
71. SAINT Software Reference Manual, version 6; Bruker AXS Inc.: Madison, WI, 2003.
72. Sheldrick, G. M. SADABS Siemens Area Detector Absorption Correction Program; University of Göttingen: Göttingen, Germany, 1996.
73. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119
74. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
75. Dyer, E.; Johnson, T. B. J. Am. Chem. Soc. 1932, 54, 777-787
76. McFarland, J. W.; Green, D.; Hubble, W. J. Org. Chem. 1970, 35, 702-704
77. Hathaway, B. J. Struct. Bonding (Berlin) 1984, 57, 55-118
78. Rosokha, S. V.; Lampeka, Y. D. J. Chem. Soc., Dalton Trans. 1993, 631-636
79. Kang, S.-G.; Song, J.; Jeong, J. H. Inorg. Chim. Acta 2004, 357, 605-610
80. Barefield, E. K. Coord. Chem. Rev. 2010, 254, 1607-1627
81. Thöm, V. J.; Boeyens, J. C. A.; McDougall, G. J.; Hancock, R. D. J. Am. Chem. Soc. 1984, 106, 3198-3207
82. Lever, A. B. P. Inorganic Electronic Spectroscopy; Elsevier: Amsterdam, The Netherlands, 1984.
83. Fabbrizzi, L.; Licchelli, M.; Poggi, A.; Sacchi, D.; Zampa, C. Polyhedron 2004, 23, 373-378
84. Fabbrizzi, L.; Foti, F.; Licchelli, M.; Maccarini, P. M.; Sacchi, D.; Zema, M. Chem.-Eur. J. 2002, 8, 4965-4972
85. Lipscombe, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375-2434.