Synthesis, structure, magnetic properties and aqueous optical citrate detection of chiral dinuclear CuII complexes

European Journal of Inorganic Chemistry

Volumn , Issue 22, 2009, Pages 3266-3274

  Khatua, Snehadrinarayan ^a   Kim, Kibong ^a   Kang, Jina ^a   Huh, Jung Oh ^a   Hong, Chang Seop ^b   Churchill, David G ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Korea University   (South Korea)

Author keywords

Chiral dicopper complex; Citrate detection; Magnetic properties; Schiff bases; Structure elucidation

Indexed keywords

AMINO ACIDS; CARBOXYLATION; COPPER COMPOUNDS; PH; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

CHIRAL DICOPPER COMPLEX; CITRATE DETECTION; DICOPPER COMPLEXES; DINUCLEAR; L-LYSINE; ONE-POT METHOD; OPTICAL-; SCHIFF BASE COMPLEXES; SCHIFF-BASE; STRUCTURE ELUCIDATION;

MAGNETIC PROPERTIES;

EID: 67949089556     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200900357     Document Type: Article

References (91)

1. a) A. D. Garnovskii, A. P. Sadimenko, M. I. Sadimenko, D. A. Garnovskii, Coord. Chem. Rev. 1998, 173, 31;
2. b) S. Yamada, Coord. Chem. Rev. 1999, 190-192, 537-555;
3. c) R. L. Lieberman, A. C Rosenzweig, Nature 2005, 434, 177-182.
4. a) C-M. Che, H.-L. Kwong, W-C. Chu, K.-F. Cheng, W.-S. Lee, H.-S. Yu, C-T. Yeung, K.-K. Cheung, Eur. J. Inorg. Chem. 2002, 6, 1456-1463;
5. b) R. Ferreira, C. Freire, B. de Castro, A. P. Carvalho, J. Pires, M. B. de Carvalho, Eur. J. Inorg. Chem. 2002, 11, 3032-3038;
6. c) A. Burkhardt, A. Buchholz, H. Goerls, W Plass, Eur. J. Inorg. Chem. 2006, 17, 3400-3406;
7. d) Y-B. Jiang, H.-Z. Kou, R.-J. Wang, A.-L. Cui, Eur. J. Inorg. Chem. 2004, 4608-4615;
8. e) S. Thakurta, P. Roy, G. Rosair, C.J. Gómez-García, E. Garribba, S. Mitra, Polyhedron 2009, 28, 695-702;
9. f) F. Tuna, L. Patron, Y. Journaux, M. Andruh, W Plass, J.-C. Trombe, J. Chem. Soc, Dalton Trans. 1999, 539-546;
10. g) H.-Y. Chao, D. G. Churchill, J. Chem. Educ. 2008, 85, 1210-1214.
11. a) E. M. Hodnett, P. D. Mooney, J. Med. Chem. 1970, 13, 786;
12. b) C. A. Bolos, G. St. Nikolov, L. Ekateriniadou, A. Kortsaris, D. A. Kyriakidis, Met.-Based Drugs 1998, 5, 323-332;
13. c) G. Plesch, C. Friebel, O. Svajlenova, J. Krätsmar-Smogrovic, D. Mlynarcik, Inorg. Chim. Acta 1988, 139, 151;
14. d) G. Cerchiaro, K. Aquilano, G. Filomeni, G. Rotilio, M. R. Ciriolo, A. M. D. C. Ferreira, J. Inorg. Biochem. 2005, 99, 1433-1450;
15. e) G. Filomeni, G. Cerchiaro, A. M. D. C. Ferreira, J. Z. Pedersen, A. De Martino, G. Rotilio, M. R. Ciriolo, J. Biol. Chem. 2007, 282, 12010-12021;
16. f) A. T. Chaviara, E. E. Kioseoglou, A. A. Pantazaki, A. C. Tsipis, P. A. Karipidis, D. A. Kyriakidis, C. A. Bolos, J. Inorg. Biochem. 2008, 102, 1749-1764;
17. g) V. C. da Silveira, J. S. Luz, C. C. Oliveira, I. Graziani, M. R. Ciriolo, A. M. D. C. Ferreira, J. Inorg. Biochem. 2008, 102, 1090-1103;
18. h) P. A. N. Reddy, M. Nethaji, A. R. Chakravarty, Eur. J. Inorg. Chem. 2004, 7, 1440-1446.
19. a) V. G. Gibson, S. K. Spitzmesser, Chem. Rev. 2003, 103, 283316;
20. b) S. Yamada, Coord. Chem. Rev. 1999, 190-192, 537-555;
21. c) H.-B. Zhu, Z.-Y. Dai, W Huang, K. Cui, S.-H. Gou, C-J. Zhu, Polyhedron 2004, 23, 1131-1137;
22. d) A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem. Int. Ed. 1999, 38, 2398-2400;
23. e) V. B. Sharma, S. L. Jain, B. Sain, J. Mol. Catal. A 2004, 219, 61-64;
24. f) J. F. Folmer-Andersen, V. M. Lynch, E. V. Anslyn, J. Am. Chem. Soc. 2005, 127, 7986-7987.
25. a) X. Yang, J. D. Ranford, J. J. Vittal, Cryst. Growth Des. 2004, 4, 781-788;
26. b) M. A. Alam, R. R. Koner, A. Das, M. Nethaji, M. Ray, Cryst. Growth Des. 2007, 7, 1818-1824.
27. For reviews of anion sensing, see: a) M. H. Filby, j. W. Steed, Coord. Chem. Rev. 2006, 250, 32003218;
28. b) R. MartinezManez, F. Sancenon, Coord. Chem. Rev. 2006,250, 3081-3093;
29. c) A. P. Davis, Coord. Chem. Rev. 2006, 250, 2939-2951;
30. d) R. Martinez-Manez, F. Sancenon, Chem. Rev. 2003, 103, 4419-4476;
31. e) P. D. Beer, J. Cadman, Coord. Chem. Rev. 2000, 205, 131-155.
32. a) S. L. Wiskur, H. Ait-Haddou, J. J. Lavigne, E. V. Anslyn, Acc. Chem. Res. 2001, 34, 963-972;
33. b) L. Fabbrizzi, M. Licchelli, A. Taglietti, Dalton Trans. 2003, 3471-3479;
34. c) J. Zhao, T. D. James, Chem. Commun. 2005, 1889-1891;
35. d) R. MartinezManez, F. Sancenon, J. Fluoresc. 2005, 15, 267-285;
36. e) K. Ghosh, G. Masanta, Tetrahedron Lett. 2006, 47, 2365-22369.
37. T. N. Popova, M. A. A. Pinheirode de Carvalho, Biochim. Biophys. Acta 1998, 1364, 307-325.
38. D. P. Simpson, Am. J. Physiol. 1983, 244, F223-F234.
39. a) C Schmuck, M. Schwegmann, J. Am. Chem. Soc. 2005,127, 3373-3379;
40. b) C. Schmuck, M. Schwegmann, Org. Biomol. Chem. 2006, 4, 836-838;
41. c) D. Parker, J. Yu, Chem. Commun. 2005, 3141-3143;
42. d) K. Ghosh, T. Sen, R. Fröhlich, Tetrahedron Lett. 2007, 48, 2935-2938;
43. e) A. L. Koner, J. Schatz, W M. Nau, U. Pischel, J. Org. Chem. 2007, 72, 3889-3895;
44. f) A. Metzger, V. M. Lynch, E. V. Anslyn, Angew. Chem. Int. Ed. Engl. 1997, 36, 862-865;
45. g) A. Metzger, E. V. Anslyn, Angew. Chem. Int. Ed. 1998, 37, 649-652;
46. h) J. J. Lavigne, E. V. Anslyn, Angew. Chem. Int. Ed. 1999, 38, 3666-3669;
47. i) L. Fabbrizzi., F. Foti, A. Taglietti, Org. Lett. 2005, 7, 2603-2606;
48. j) M. I. Burguete, F. Galindo, S. V. Luis, L. Vigara, Dalton Trans. 2007, 4027-4033;
49. k) M. P. Clares, C. Lodeiro, D. Fernandez, A. J. Parola, F. Pina, E. Garcia-Espana, C Soriano, R. Tejero, Chem. Commun. 2006, 3824-3826;
50. l) M. Comes, G. Rodríguez-López, M. D. Marcos, R. Martínez-Máñez, F. Sancenón, J. Soto, L. A. Villaescusa, P. Amorós, D. Beltrán, Angew. Chem. Int. Ed, 2005, 44, 2918-2922;
51. m) L. A. Cabell, M. D. Best, J. J. Lavigne, S. E. Schneider, D. M. Perreault, M. K. Monahan, E. V. Anslyn, J. Chem. Soc Perkin Trans. 2 2001, 315-323.
52. [11]a) A. Kazemzadeh, F. Moztarzadeh, Sens. Actuators, B 2005, 106, 832-836;
53. b) L. Tang, J. Park, H.-J. Kim, Y. Kim, S. J. Kim, J. Chin, K. M. Kim, J. Am. Chem. Soc 2008, 130, 12606-12607;
54. c) M. Boiocchi, M. Bonizzoni, L. Fabbrizzi, G Piovani, A. Taglietti, Angew. Chem. Int. Ed. 2004, 43, 3847-3852;
55. d) A. M. Costero, M. Colera, P. Gavina, S. Gil, U. Llaosa, Tetrahedron 2008, 64, 1151-1151;
56. e) K. Ghosh, G. Masanta, Tetrahedron Lett. 2008, 49, 2592-2597;
57. f) Y-P. Yen, K.-W. Ho, Tetrahedron Lett. 2006, 47, 1193-1196.
58. The use of a Schiff base species as a sensor; a) D. Ray, P. K. Bharadwaj, Inorg. Chem. 2008, 47, 2252-2254;
59. b) P. Roy, K. Dhara, M. Manassero, J. Ratha, P. Banerjee, Inorg. Chem. 2007, 46, 6405-6412;
60. c) K. Dhara, K. Sarkar, P. Roy, M. Nandi, A. Bhaumik, P. Banerjee, Tetrahedron 2008, 64, 3153-3159;
61. d) D. Saravanakumar, S. Devaraj, S. Iyyampillai, K. Mohandossb, M. Kandaswamy, Tetrahedron Lett. 2008, 49, 127-132.
62. a) L. Fabbrizzi, N. Marcotte, F. Stomeo, A. Taglietti, Angew. Chem. Int. Ed. 2002, 41, 3811-3814;
63. b) J. F. Folmer-Andersen, V. M. Lynch, E. V. Anslyn, Chem. Eur. J. 2005, 11, 5319-5326.
64. a) S. Khatua, S. H. Choi, J. Lee, K. Kim, Y. Do, D. G. Churchill, Inorg. Chem. 2009, 48, 2993-2999;
65. b) S. Khatua, S. H. Choi, J. Lee, J. O. Huh, Y. Do, D. G. Churchill, Inorg. Chem. 2009, 48, 1799-1801.
66. For a description of common chemical explosion hazards including Perchlorates and closely related species, see:
67. c) D. G. Churchill, J. Chem. Educ. 2006, 83, 1798.
68. a) C.-T. Yang, M. Vetrichelvan, X. Yang, B. Moubaraki, K. S. Murray, J. J. Vittal, Dalton Trans. 2004, 113-121;
69. b) X. Wang, J. Ding, J. J. Vittal, Inorg. Chim. Acta 2006, 359, 3481-3490;
70. c) S. M. Couchman, J. C. Jeffery, P. Thornton, M. D. Ward, J. Chem. Soc., Dalton Trans. 1998, 1163-1169;
71. d) V. K. Muppidi, S. Pal, Eur. J. Inorg. Chem. 2006, 14, 2871-2877.
72. a) L. Rodriguez, E. Labisbal, A. Sousa-Pedrares, J. A. GarciaVazquez, J. Romero, M. L. Duran, I A. Real, A. Sousa, Inorg. Chem. 2006, 45, 7903-7914;
73. b) B. Sreenivasulu, F. Zhao, S. Gao, J. J. Vittal, Eur. J. Inorg. Chem. 2006, 13, 2656-2670.
74. W. H. Crawford, H. W Richardson, J. R. Wasson, D. J. Hodgson, W E. Hatfield, Inorg. Chem. 1976, 15, 2107-2110.
75. a) A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566;
76. b) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
77. a) K. Niikura, A. Metzger, E. V. Anslyn, J. Am. Chem. Soc. 1998, 120, 8533-8534;
78. b) S. L. Wiskur, H. A. Haddou, J. J. Lavigne, E. V. Anslyn, Acc, Chem. Res. 2001, 34, 963-972;
79. c) B. T. Nguyen, E.V. Anslyn, Coord Chem. Rev. 2006, 250, 3118-3127;
80. d) L. Fabbrizzi, M. Licchelli, A. Taglietti., Dalton Trans. 2003, 3471-3479;
81. e) D. J. Oh, K. H. Ahn, Org. Lett. 2008, 10, 3539;
82. f) M. S. Han, D. H. Kim, Angew. Chem. Int. Ed. 2002, 41, 3809;
83. g) L. Zhu, Z. Zhong, E. V. Anslyn, J. Am. Chem. Soc, 2005, 127, 4260-4269;
84. h) J. F. Fotmer-Andersen, V. M. Lynch, E.V. Anslyn, Chem. Eur. J. 2005, 11, 5319-5326.
85. a) A. K. Conners, Binding Constants, Wiley, New York, 1987;
86. b) B. Valeur, J. Pouget, J. Bourson, M. Kaschke, N P. Ernsting, J. Phys. Chem. 1992, 96, 6545.
87. SMART and. SAINT, Area Detector Software Package and. SAX Area Detector Integration Program, Bruker Analytical X-ray, Madison, WI, 1997.
88. SADABS, Area Detector Absorption Correction Program, Bruker Analytical X-ray, Madison, WI, 1997.
89. G. M. Sheldrick, SHELXS-97: Program for Crystal Structure Determination, Acta Crystallogr., Sect. A 1990, 46, 467-473.
90. a) G. M. Sheldrick, 1999, SHELXL-97: Program for Crystal Structure Solution and Refinements, University of Göttingen, Göttingen, Germany;
91. b) G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112-122.