New terpyridine-containing macrocycle for the assembly of dimeric Zn(II) and Cu(II) complexes coupled by bridging hydroxide anions and π-stacking interactions

Inorganic Chemistry

Volumn 43, Issue 16, 2004, Pages 5134-5146

  Bazzicalupi, Carla ^a   Bencini, Andrea ^a   Berni, Emanuela ^a   Bianchi, Antonio ^a   Danesi, Andrea ^a   Giorgi, Claudia ^a   Valtancoli, Barbara ^a   Lodeiro, Carlos ^b   Lima, João Carlos ^b   Pina, Fernando ^b   Bernardo, M Alexandra ^b,c  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^c INSTITUTO SUPERIOR DE CIÊNCIAS DA SAÚDE EGAS MONIZ   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

2,5,8,11,14 PENTAAZA[15](6,6'')CYCLO[2,2':6',2'']TERPYRIDINOPHANE; ACID; ANION; BASE; COPPER COMPLEX; DIMER; HYDROXIDE; LEAD; LIGAND; MACROCYCLIC COMPOUND; NITROGEN; POLYAMINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; FLUORESCENCE; MOLECULAR INTERACTION; PH; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SPECTROPHOTOMETRY; SYNTHESIS; X RAY ANALYSIS;

EID: 4043076284     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic049660l     Document Type: Article

References (118)

1. (a) Bradshaw, J. S., Krakowiak, K. E., Izatt, R. M., Eds.; Aza-Crown Macrocycles: Chemistry of Heterocyclic Compounds, Vol. 51; Wiley: New York, 1993.
2. (b) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529-2586.
3. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: New York, 1995.
4. (a) Lindoy, L. F. The Chemistry of Macrocyclic Ligand Complexes; Cambridge University Press: Cambridge, U.K., 1992.
5. (b) Lindoy, L. F. Pure Appl. Chem. 1997, 69, 2179-2184.
6. (a) Raidt, R.; Neuburger, M.; Kaden, T. A. Dalton Trans. 2003, 1292-1298.
7. (b) Kaden, T. A. Coord. Chem. Rev. 1999, 190-192, 371-389.
8. Blake, A. J.; Champness, N. R.; Hubberstey, P.; Li, W. S.; Schröder, M.; Withersby, M. A. Coord. Chem. Rev. 1999, 183, 117-138.
9. Nelson, J.; McKee, V.; Morgan, G. Prog. Inorg. Chem. 1998, 47, 167-316.
10. (a) Katrintzky, A. R., Rees, C. W., Schriven, E., Eds.; Comprehensive Coordination Chemistry; Pergamon: Oxford, U.K., 1996; Vol. 9.
11. (b) Bencini, A.; Bianchi, A.; Paoletti, P.; Paoli, P. Coord. Chem. Rev. 1992, 120, 51-85.
12. (a) Fry, F. H.; Fallon, G. D.; Spiccia, L. Inorg. Chim. Acta 2003, 346, 57-66.
13. (b) Fry, F. H.; Jensen, P.; Kepert, C. M.; Spiccia, L. Inorg. Chem. 2003, 42, 5637-5644.
14. (c) Fry, F. H.; Moubaraki, B.; Murray, K. S.; Spiccia, L.; Warren, M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 2003, 866-871.
15. (d) Brudenell, J. S.; Spiccia, L.; Hockless, D. C. R.; Tiekink, E. R. T. J. Chem. Soc., Dalton Trans. 1999, 1475-1482.
16. Ghosh, P.; Bharadwaj, P. K.; Roy, J.; Ghosh, S. J. Am. Chem. Soc. 1997, 119, 11903-11909.
17. (a) Depree, C. V.; Beckmann, U.; Heslop, K.; Brooker, S. J. Chem. Soc., Dalton Trans. 2003, 3071-3081.
18. (b) Brooker, S. Coord. Chem. Rev. 2001, 222, 33-56.
19. (a) Lamarque, L.; Miranda, C.; Navarro, P.; Escartí, F.; García-España, E.; LaTorre, J.; Ramírez, J. A. Chem. Commun. 2000, 1337-1338.
20. (b) Lamarque, L.; Navarro, P.; Miranda, C.; Aran, V. J.; Ochoa, C.; Escartí, F.; García-España, E.; LaTorre, J.; Luis, S. V.; Miravet, J. F. J. Am. Chem. Soc. 2001, 123, 10560-10570.
21. (a) Ambrosi, G.; Dapporto, P.; Formica, M.; Fusi, V.; Giorgi, L.; Guerri, A.; Micheloni, M.; Paoli, P.; Pontellini, R.; Rossi, P. Chem.-Eur. J. 2003, 9, 800-810.
22. (b) Dapporto, P.; Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M.; Paoli, P.; Pontellini, R.; Rossi, P. Inorg. Chem. 2001, 40, 6186-6192.
23. Guerriero, P.; Tamburini, S.; Vigato, P. A. Coord. Chem. Rev. 1995, 139, 17-243.
24. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruenig, R. L. Chem. Rev. 1991, 91, 1721-1985.
25. (a) Fabbrizzi, L.; Licchelli, M.; Rabaioli, G.; Taglietti, A. Coord. Chem. Rev. 2000, 205, 85-108.
26. (b) Fabbrizzi, L.; Licchelli, M.; Pallavicini, P. Acc. Chem. Res. 1999, 32, 846-853.
27. (c) Fabbrizzi, L.; Licchelli, M.; Taglietti, A. J. Chem. Soc., Dalton Trans. 2003, 3471-3479.
28. (d) Amendola, V.; Fabbrizzi, L.; Mangano, C.; Pallavicini, P. Struct. Bonding (Berlin) 2001, 99, 79-115
29. (e) Hortala, M. A.; Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. J. Am. Chem. Soc. 2003, 125, 20-21.
30. (a) Blake, A. J.; Demartin, F.; Devillanova, F. A.; Garau, A.; Isaia, F.; Lippolis, V.; Schröder, M.; Verani, G. J. Chem. Soc., Dalton Trans. 1996, 3705-3712.
31. (b) Blake, A. J.; Casabo, J.; Devillanova, F. A.; Escriche, L.; Garau, A.; Isaia, F.; Lippolis, V.; Kivekas, R.; Muns, V.; Schröder, M.; Sillampää, R.; Verani, G. J. Chem. Soc., Dalton Trans. 1999, 1085-1092.
32. (c) Arca, M.; Blake, A. J.; Casabo, J.; Demartin, F.; Devillanova, F. A.; Garau, A.; Isaia, F.; Lippolis, V.; Kivekas, R.; Muns, V.; Schröder, M.; Verani, G.; J. Chem. Soc., Dalton Trans. 2001, 1180-1188.
33. (a) Azéma, J.; Galaup, C.; Picard, C.; Tisnès, P.; Ramos, P.; Juanes, O.; Rodrìguez-Ubis, J. C.; Brunet, E. Tetrahedron 2000, 56, 2673-2681 and references therein.
34. (b) Galaup, C.; Carrié, M.-C.; Tisnès, P.; Picard, C. Eur. J. Org. Chem. 2001, 2165-2175.
35. (c) Galaup, C.; Couchet, J. M.; Picard, C.; Tisnès, P. Tetrahedron Lett. 2001, 42, 6275-6278.
36. (a) Rodriguez-Ubis, J.-C.; Alpha, B.; Plancherel, D.; Lehn, J. M. Helv. Chim. Acta 1984, 67, 2264-2269.
37. (b) Alpha, B.; Lehn, J. M.; Mathis, G. Angew. Chem., Int. Ed. Engl. 1987, 99, 259-261.
38. (c) Cesario, M.; Guilhem, J.; Pascard, C.; Anklam, E.; Lehn, J. M.; Pietraskiewicz, M. Helv. Chim. Acta 1991, 74, 1157-1162.
39. (d) Bkouche-Waksmann, I.; Guilhem, J.; Pascard, C.; Alpha, B.; Deschenaux, Lehn, J. M. Helv. Chim. Acta 1991, 75, 1163-1170.
40. (e) Lehn, J. M.; Regnouf de Vains, J. B. Helv. Chim. Acta 1992, 75, 1221-1236.
41. (f) Paul-Roth, C. O.; Lehn, J.-M.; Guilheim, J.; Pascard, C. Helv. Chim. Acta 1995, 78, 1895-1903 and references therein.
42. (a) Vidal, P.-L.; Divisia-Blohom, B.; Bidan, G.; Kern, J.-M.; Sauvage, J.-P.; Hazemann, J.-L. Inorg Chem. 1999, 38, 4203-4210.
43. (b) Weck, M.; Mohr, B.; Sauvage, J.-P.; Grubbs, R. H. J. Org. Chem. 1999, 64, 5463-5471.
44. (c) Rapenne, G.; Dietrich-Buchecker, C.; Sauvage, J.-P. J. Am. Chem. Soc. 1999, 121, 994-1001.
45. (d) Meyer, M.; Albrecht-Gary, A.-M.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Inorg. Chem. 1999, 38, 2279-2287.
46. (a) Barigelletti, F.; De Cola, L.; Balzani, V.; Belser, P.; Von Zelewsky, A.; Vögtle, F.; Ebmeyer, F.; Grammenudi, S. J. Am. Chem. Soc. 1989, 111, 4662-4668.
47. (b) Balzani, V.; Ballardini, R.; Bolletta, F.; Gandolfi, M. T.; Juris, A.; Maestri, M.; Manfrin, M. F.; Moggi, L.; Sabbatini, N. Coord. Chem. Rev. 1993, 125, 75-88 and references therein.
48. (c) Sabbatini, N.; Guardigli, M.; Lehn, J.-M. Coord. Chem. Rev. 1993, 123, 201-228.
49. (d) Balzani, V.; Credi, A.; Venturi, M. Coord. Chem. Rev. 1998, 171, 3-16 and references therein.
50. (a) Bazzicalupi, C.; Bencini, A.; Fusi, V.; Giorgi, C.; Paoletti, P.; Valtancoli, B. Inorg. Chem. 1998, 37, 941-948.
51. (b) Bazzicalupi, C.; Bencini, A.; Fusi, V.; Giorgi C.; Paoletti, P.; Valtancoli, B. J. Chem. Soc., Dalton Trans. 1999, 393-400.
52. (c) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Giorgi, C.; Fusi, V.; Valtancoli, B.; Bernardo, M. A.; Pina, F. Inorg. Chem. 1999, 38, 3806-3813.
53. (d) Bazzicalupi, C.; Beconcini, A.; Bencini, A.; Giorgi, C.; Fusi, V.; Masotti, A.; Valtancoli, B. J. Chem. Soc., Perkin Trans. 2 1999, 1675-1682.
54. (e) Bencini, A.; Bernardo, M. A.; Bianchi, A.; Fusi, V.; Giorgi, C.; Pina, F.; Valtancoli, B. Eur. J. Inorg. Chem. 1999, 1911-1918.
55. (a) Bazzicalupi, C.; Bencini, A.; Ciattini, S.; Giorgi, C.; Masotti, A.; Paoletti, P.; Valtancoli, B.; Navon, N.; Meyerstein, D. J. Chem. Soc., Dalton Trans. 2000, 2383-2391.
56. (b) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Giorgi, C.; Fusi, V.; Masotti, A.; Valtancoli, B.; Roque, A.; Pina, F. Chem. Commun. 2000, 561-562.
57. (c) Bencini, A.; Bianchi, A.; Lodeiro, C.; Masotti, A.; Parola, A. J.; Melo, J. S.; Pina, F.; Valtancoli, B. Chem. Commun. 2000, 1639-1640.
58. (d) Bencini, A.; Bianchi, A.; Fusi, V.; Giorgi, C.; Masotti, A.; Paoletti, P. J. Org. Chem. 2000, 65, 7686-7689.
59. (e) Bazzicalupi, C.; Bencini, A.; Berni, E.; Bianchi, A.; Giorgi, C.; Fusi, V.; Valtancoli, B.; Lodeiro, C.; Roque, A.; Pina, F. Inorg. Chem. 2001, 40, 6172-6179.
60. (a) Lodeiro, C.; Parola, A. J.; Pina, F.; Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Giorgi, C.; Masotti, A.; Valtancoli, B. Inorg. Chem. 2001, 40, 2968-2975.
61. (b) Arranz, P.; Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Ciattini, S.; Fomasari, P.; Giorgi, C.; Valtancoli, B. Inorg. Chem. 2001, 40, 6383-6389.
62. Smith, R. M.; Martell, A. E. NISTStability Constants Database, version 4.0; National Institute of Standards and Technology: Washington, DC, 1997.
63. Bencini, A.; Bianchi, A.; García-España, E.; Giusti, M.; Micheloni, M.; Paoletti, P. Inorg. Chem. 1987, 26, 681-686.
64. Offermann, W.; Vögtle, F. Synthesis 1977, 272-273.
65. Hyperchem, release 6.01 for Windows; Hypercube, Inc.: Gainsville, FL, 2000.
66. 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.
67. Sheldrick, G. M. SHELXL-97; Göttingen, Germany, 1997.
68. Bianchi, A.; Bologni, L.; Dapporto, P.; Micheloni, M.; Paoletti, P. Inorg. Chem. 1984, 23, 1201-1207.
69. (a) Gran, G. Analyst (London) 1952, 77, 661-663.
70. (b) Rossotti, F. J.; Rossotti, H. J. Chem. Educ. 1965, 42, 375-378.
71. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753.
72. Richman, J. E.; Atkins, T. J. J. Am. Chem. Soc. 1974, 96, 2268-2270.
73. Bencini, A.; Bianchi, A., García-España, E.; Micheloni, M.; Ramirez, J. A. Coord. Chem. Rev. 1999, 118, 97-156.
74. Albano, G.; Balzani, V.; Constable E. C.; Maestri, M.; Smith, D. R. Inorg. Chim. Acta 1998, 277, 225-231.
75. Sarkar, A.; Chakravorti, S. J. Luminescence 1995, 63, 143-148.
76. A large number of structurally characterized μ-OH dizinc complexes have been reported in the literature. Some exemplifying papers are (a) Bell, M.; Edwards, A. J.; Hoskins, B. F.; Kachab, E. H.; Robson, R. J. Am. Chem. Soc. 1989, 111, 3603-3610.
77. (b) Grannas, M. J.; Hoskins, B. F.; Robson, R. Chem. Commun. 1990, 1644-1646.
78. (c) Grannas, M. J.; Hoskins, B. F.; Robson, R. Inorg. Chem. 1994, 33, 1071-1079.
79. (d) Tan, L. H.; Taylor, M. R.; Wainwright, K. P.; Duckworth, P. A. J. Chem. Soc., Dalton Trans. 1993, 2921-2928.
80. (e) Hermann, J.; Erxleben, A. Inorg. Chim. Acta 2000, 304, 125-129.
81. (f) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Fusi, V.; Paoletti, P.; Valtancoli, B. Chem. Commun. 1994, 881-882.
82. (g) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Fusi, V.; Mazzanti, L.; Paoletti, P.; Valtancoli, B. Inorg. Chem. 1995, 34, 3003-3013.
83. (h) Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Fusi, V.; Paoletti, P., Piccardi, G.; Valtancoli, B. Inorg. Chem. 1995, 34, 5622-5630.
84. (i) Asato, E.; Furutachi, H.; Kawahashi, T.; Mikuriya, M. J. Chem. Soc., Dalton Trans. 1995, 3897-3904.
85. 2O dizinc complexes have been reported: (a) Wolodkiewicz, W.: Glowiak, T. Pol. J. Chem. 2001, 75, 299-306.
86. (b) Johnson, J. A.; Olmstead, M. M.; Stolzenberg, A. M.; Balch, A. L. Inorg. Chem. 2001, 40, 5585-5595.
87. (c) Barrios, A. M.; Lippard, S. J. Inorg. Chem. 2001, 40, 1060-1064.
88. (a) Rosi, N. L.; Eddaoudi, M.; Kim, J.; O'Keeffe, M.; Yaghi, O. M. Angew. Chem., Int. Ed. 2002, 41, 284-287.
89. (b) Tao, J.-X.; Shi, J.-X.; Tong, M.-L.; Zhang, X.-X.; Chen, X.-H. Inorg. Chem. 2001, 40, 6328-6330.
90. (c) Mikuriya, M.; Minowa, K. Inorg. Chem. Commun. 2000, 3, 227-230.
91. (d) Berreau, L. M.; Allred, R. A.; Makowska-Grzyska, M. M.; Arif, A. M. Chem. Commun. 2000, 1423-1424.
92. (e) Hammes, B. S.; Carrano, C. J. Chem. Commun. 2000, 1635-1636.
93. (f) Gerrard, L. A.; Wood, P. T. Chem. Commun. 2000, 2107-2108.
94. (g) Looney, A.; Han, R.; Gorrell, I. B.; Cornebise, M.; Yoon, K.; Parkin, G.; Rheingold, A. L. Organometallics 1995, 14, 274-288.
95. (h) Flassbeck, C.; Wieghardt, K.; Bill, E.; Butzlaff, C.; Trautwein, A. X.; Nuber, B.; Weiss, J. Inorg. Chem. 1992, 31, 21-26.
96. (i) Murthy, N. N.; Karlin, K. D. Chem. Commun. 1993, 1236-1238.
97. (j) Branscombe, N. D. J.; Blake, A. J.; Marin-Becerra, A.; Li, W.; Parsons, S.; Ruiz-Ramirez, L.; Schroder, M. Chem. Commun. 1996, 2573-2574.
98. (k) Chaudhuri, P.; Stockheim, C.; Wieghardt, K.; Deck, W.; Gregorzik, R.; Vahrenkamp, H.; Nuber, B.; Weiss, J. Inorg. Chem. 1992, 31, 1451-1457.
99. (a) Vaidhyanathan, R.; Natarajan, S.; Rao, C. N. R. Chem. Mater. 2001, 13, 3524-3533.
100. (b) Lartigue-Bourdeau, C.; Chanh, N. B.; Duplessix, R.; Gallois, B. J. Phys. Chem. Solids 1993, 54, 349-356.
101. (c) Gonzalez-Duarte, P.; Clegg, W.; Casals, I.; Sola, J.; Rius, J. J. Am. Chem. Soc. 1998, 120, 1260-1266.
102. (d) Puget, R.; Jannin, M.; De Brauer, C.; Perret, R. Acta Crystallogr., Sect. C 1991, 47, 1803-1805.
103. (a) Blake, A. J.; Devillanova, F. A.; Garau, A.; Harrison, A.; Isaia, F.; Lippolis, V.; Tiwary, S. K.; Schroeder, M.; Verani, G.; Whittaker, G. J. Chem. Soc., Dalton Trans. 2002, 4389-4394.
104. (b) Cheng, M.; Moore, D. R.; Reczek, J. J.; Chamberlain, B. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 8738-8749.
105. (c) Plater, M. J.; Foreman, M. R. St. J.; Gelbrich, T.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 2000, 1995-2000.
106. (d) Tao, J.; Tong, M.-L.; Shi, J.-X.; Chen, X.-M.; Weng Ng, S. Chem. Commun. 2000, 2043-2044.
107. (e) Fusch, E. C.; Lippert, B. J. Am. Chem. Soc. 1994, 116, 7204-7209.
108. (f) Mamula, O.; von Zelewsky, A.; Bark, T.; Stoeckli-Evans, H.; Neels, A.; Bernardinelli, G. Chem.-Eur. J. 2000, 6, 3575-3585.
109. (a) Adams, H.; Bastida, R.; Fenton, D. E.; Macias, A.; Spey, S. E.; Valencia, L. J. Chem. Soc., Dalton Trans. 1999, 4131-4137.
110. (b) Chu, F.; Smith, J.; Lynch, V. M.; Anslyn, E. V. Inorg. Chem. 1995, 34, 5689-5690.
111. (c) Furuta, H.; Ishizuka, T.; Osuka, A. J. Am. Chem. Soc. 2002, 124, 5622-5623.
112. (a) Ern, J.; Bock, A.; Oddos-Marcel, L.; Rengel, H.; Wegner, G.; Trommsdorff, H. P.; Kryschi, C. J. Phys. Chem. A 1999, 103, 2446-2450 and references therein.
113. (b) Angiolini, A.; Caretti, D.; Giorgini, L.; Salatelli, E. e-Polym. 2001, 21, 1-12 and references therein.
114. (a) Bazzicalupi, C.; Bencini, A.; Berni, E.; Bianchi, A.; Borsari, L.; Giorgi, C.; Valtancoli, B.; Lodeiro, C.; Lima, J. C.; Parola, A. J.; Pina, F. J. Chem. Soc., Dalton Trans. 2004, 591-597.
115. (b) Vicente, M.; Bastida, R.; Lodeiro, C.; Macías, A.; Parola, A. J.; Valencia, L.; Spey, S. E. Inorg. Chem. 2003, 42, 6768-6779.
116. De Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. Chem. Commun. 1996, 2399-2340.
117. Alves, S.; Pina, F.; Albelda, M. T.; García-España, E.; Soriano, C.; Luis, S. V. Eur. J. Inorg. Chem. 2001, 2, 405-412. Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington, DC, 1993.
118. Alves, S.; Pina, F.; Albelda, M. T.; García-España, E.; Soriano, C.; Luis, S. V. Eur. J. Inorg. Chem. 2001, 2, 405-412. Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington, DC, 1993.