Synthesis, structural characterization, and sensing properties of clickable unsymmetrical 1,1′-disubstituted ferrocene-triazole derivatives

Organometallics

Volumn 31, Issue 5, 2012, Pages 2085-2096

  Otón, Francisco ^a   González, María Del Carmen ^b   Espinosa, Arturo ^b   Tárraga, Alberto ^b   Molina, Pedro ^b  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING MODES; BLUE-SHIFTED; CLICK REACTION; COMPLEXATION PROPERTIES; EMISSION BANDS; FERROCENES; LOW-ENERGY BAND; NMR TITRATION; RED SHIFT; SENSING PROPERTY; SPECTROSCOPIC TECHNIQUE; STRUCTURAL CHARACTERIZATION; STRUCTURAL FEATURE; THEORETICAL CALCULATIONS; TRIAZOLE RING;

BINDING ENERGY; IRON COMPOUNDS; LEAD; METAL COMPLEXES; NITROGEN COMPOUNDS; ORGANOMETALLICS; POSITIVE IONS; ZINC;

CADMIUM COMPOUNDS;

EID: 84858123198     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300093c     Document Type: Article

References (85)

1. Seyferth, D.; Withers, H. P., Jr. Organometallics 1982, 1, 1275-1282
2. Wright, M. E. Organometallics 1990, 9, 853-856
3. Lai, L.-L.; Dong, T.-Y. J. Chem. Soc., Chem. Commum. 1994, 2347-2348
4. Iftime, G.; Moreau-Bossuet, C.; Manoury, E.; Balavoine, G. G. A. J. Chem. Soc., Chem. Commun. 1996, 527-528
5. Dong, T.-Y.; Lai, L.-L. J. Organomet. Chem. 1996, 509, 131-134
6. Grossel, M. C.; Hamilton, D. G.; Vine, T. A. Tetrahedron Lett. 1997, 38, 4639-4642
7. Xu, Y.; Kraatz, H. B. Tetrahedron Lett. 2001, 42, 2601-2603
8. Rodríguez, J. G.; Pleite, S. J. Organomet. Chem. 2001, 637-639, 230-239
9. Chiffre, J.; Averseng, F.; Balavoine, G. G. A.; Daran, J. C.; Iftime, G.; Lacroix, P. G.; Manoury, E.; Nakatani, K. Eur. J. Inorg. Chem. 2001, 2221-2226
10. Yu, C. J.; Wan, Y.; Yowanto, H.; Li, J.; Tao, C.; James, M. D.; Tan, C. L.; Blackburn, G. F.; Meade, T. J. J. Am. Chem. Soc. 2001, 123, 11155-11161
11. Song, H.; Kerman, K.; Kraatz, H. B. Chem. Commun. 2008, 502-504
12. Moriuchi, T.; Nomoto, A.; Yoshida, K.; Ogawa, A.; Hirao, T. J. Am. Chem. Soc. 2001, 123, 68-75
13. Kuik, Á.; Skoda-Földes, R.; Jánosi, L.; Collar, L. Synthesis 2007, 10, 1456-1458
14. Butler, I. R.; Quayle, S. C. J. Organomet. Chem. 1998, 552, 63-68
15. Okamura, T.; Sakauye, K.; Ueyama, N.; Nakamura, A. Inorg. Chem. 1998, 37, 6731-6736
16. Argyropoulos, N.; Coutouli-Argyropoulo, E. J. Organomet. Chem. 2002, 654, 117-122
17. Coutouli-Argyropoulo, E.; Sideris, C.; Kokkinidis, G. J. Organomet. Chem. 2006, 691, 3909-3918
18. Bertina, P. A.; Maedeb, T. J. Tetrahedron Lett. 2009, 50, 5409-5412
19. Molina, P.; Tárraga, A.; Caballero, A. Eur. J. Inorg. Chem. 2008, 3401-3417
20. Molina, P.; Tárraga, A.; Alfonso, M. Eur. J. Org. Chem. 2011, 4505-4518
21. Romero, T.; Caballero, A.; Tárraga, A.; Molina, P. Org. Lett. 2009, 11, 3466-3469
22. Sola, A.; Otón, F.; Espinosa, A.; Tárraga, A.; Molina, P. Dalton Trans. 2011, 40, 12548-12559
23. Tárraga, A.; Otón, F.; Espinosa, A.; Velasco, M. D.; Molina, P.; Evans, D. J. Chem. Commun. 2004, 458-459
24. Otón, F.; Tárraga, A.; Molina, P. Org. Lett. 2006, 8, 2107-2110
25. Otón, F.; Espinosa, A.; Tárraga, A.; Ramirez de Arellano, C.; Molina, P. Chem. Eur. J. 2007, 13, 5742-5752
26. Dawson, W. R.; Windsor, M. W. J. Phys. Chem. 1968, 72, 3251-3260
27. Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen, Göttingen, Germany, 1996.
28. Sheldrick, G. M. SHELX-97: An Integrated System for Solving and Refining Crystal Structures from Diffraction Data; University of Göttingen, Göttingen, Germany, 1996.
29. Neese, F. ORCA-An ab Initio, Density Functional and Semiempirical Program Package, Version 2.8.0; Universität Bonn, Bönn, Germany, 2010; http://www.thch.uni-bonn.de/tc/orca/.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
31. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
32. Neese, F.; Wennmohs, F.; Hansen, A.; Becker, U. Chem. Phys. 2009, 356, 98-109
33. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
34. Grimme, S. J. Comput. Chem. 2004, 25, 1463-1476
35. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
36. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys., 1994, 100, 5829-5835; basis sets may be obtained from the Basis Set Exchange (BSE) software and the EMSL Basis Set Library: https://bse.pnl.gov/bse/portal.
37. Feller, D. J. Comput. Chem. 1996, 17, 1571-1586
38. Wiberg, K. Tetrahedron 1968, 24, 1083-1096
39. Mayer, I. Chem. Phys. Lett. 1983, 97, 270-274
40. Mayer, I. Int. J. Quantum Chem. 1984, 26, 151-154
41. Mayer, I. Theor. Chim. Acta 1985, 67, 315-322
42. Mayer, I. In Modelling of Structure and Properties of Molecules; Maksic, Z. B., Ed.; Wiley: New York, Chichester, Brisbane, Toronto, 1987.
43. Bridgeman, A. J.; Cavigliasso, G.; Ireland, L. R.; Rothery, J. Dalton Trans. 2001, 2095-2108
44. Bader, R. F. W. In Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K., 1990.
45. Bader, R. F. W. Chem. Rev. 1991, 91, 893-928
46. Matta, C. F.; Boyd, R. J. In The Quantum Theory of Atoms in Molecules; Matta, C. F.; Boyd, R. J., Eds.; Wiley-VCH: New York, 2007; pp 1-34.
47. Biegler-König, F.; Schönbohm, J. AIM2000 v. 2.0; 2002; http://www.aim2000.de/.
48. Biegler-König, F.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545-559
49. Biegler-König, F.; Schönbohm, J. J. Comput. Chem. 2002, 23, 1489-1494
50. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford, CT, 2009.
51. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics 1996, 14, 33-38 http://www.ks.uiuc.edu/Research/vmd/
52. Mercury-visualization and analysis of crystal structures: Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453-457
53. Rostovtsev, V.; Green, L. G.; Kokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
54. Tornoe, C. V.; Christensen, C.; Medal, M. J. Org. Chem. 2002, 67, 3057-3064
55. Siemeling, U.; Rother, D. J. Organomet. Chem. 2009, 694, 1055-1058
56. Serr, B. R.; Andersen, K. A.; Elliot, C. M.; Anderson, O. P. Inorg. Chem. 1988, 27, 4499-4504
57. Richardson, D. E.; Taube, H. Inorg. Chem. 1981, 20, 1278-1285
58. Specfit/32 Global Analysis System; Spectrum Software Associates, 1999, - 2004; SpecSoft@compuserve.com
59. Lloveras, V.; Caballero, A.; Tárraga, A.; Velasco, M. D.; Espinosa, A.; Wurst, K.; Evans, D. J.; Vidal-Gancedo, J.; Rovira, C.; Molina, P.; Veciana, J. Eur. J. Inorg. Chem. 2005, 2436-2450
60. Caballero, A.; García, R.; Espinosa, A.; Tárraga, A.; Molina, P. J. Org. Chem. 2007, 72, 1161-1173
61. Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. J. Org. Chem. 2008, 73, 5489-5497
62. Martínez, R.; Zapata, F.; Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. Arkivoc. 2010, iii, 124-144
63. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910
64. Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. J. Org. Chem. 2008, 73, 5489-5497
65. Zapata, F.; Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. J. Org. Chem. 2009, 74, 4787-4796
66. Evans, A. J.; Watkins, S. E.; Craig, C.; Colbran, S. B. Dalton Trans. 2002, 983-994
67. Potts, K. T.; Keshavarz-K., M.; Tham, F. S.; Abruña, H. D.; Arana, C. R. Inorg. Chem. 1993, 32, 4422-4435
68. Cui, X.; Carapuca, H. M.; Delgado, R.; Drew, M. G. B.; Felix, V. Dalton Trans. 2004, 1743-1751
69. Otón, F.; Tárraga, A.; Espinosa, A.; Velasco, M. D.; Molina, P. Dalton Trans. 2006, 3685-3692
70. Sato, M.; Katada, M.; Nakashima, S.; Sano, H. J. Chem. Soc., Dalton Trans. 1990, 1979-1984
71. Plenio, H.; Aberle, C.; Shihadeh, Y. A.; Lloris, J. M.; Martínez-Máñez, R.; Pardo, T.; Soto, J. Chem. Eur. J. 2001, 7, 2848-2861
72. Marder, S. R.; Perry, J. W.; Tiemann, B. G. Organometallics 1991, 10, 1896-1901
73. Coe, B. J.; Jones, C. J.; McCleverty, J. A.; Bloor, D.; Cross, G. J. J. Organomet. Chem. 1994, 464, 225-232
74. Mller, T. J.; Netz, A.; Ansorge, M. Organometallics 1999, 18, 5066-5074
75. Carr, J. D.; Coles, S. J.; Asan, M. B.; Hurthouse, M. B.; Malik, K. M. A.; Tucker, J. H. R. J. Chem. Soc., Dalton Trans. 1999, 57-62
76. Geoffroy, G. L.; Wrighton, M. S. Organometallic Photochemistry; Academic Press: New York, 1979.
77. Gray, H. B.; Sohn, Y. S.; Hendrickson, N. J. Am. Chem. Soc. 1971, 93, 3603-3612
78. Barlow, S.; Bunting, H. E.; Ringham, C.; Green, J. C.; Bublitz, G. U.; Boxer, S. G.; Perry, J. W.; Marder, S. R. J. Am. Chem. Soc. 1999, 121, 3715-3723
79. Southhard, G. E.; Curtis, M. D. Organometallics 2001, 20, 508-522
80. Naka, K.; Uemura, T.; Chujo, Y. Macromolecules 2000, 33, 6965-6969
81. Shortreed, M.; Kopelman, R.; Kuhn, M.; Hoyland, B. Anal. Chem. 1996, 68, 1414-1418
82. Connors, K. A. Binding Constants; Wiley: New York, 1987.
83. Robin, M.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 10, 247-422
84. Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
85. Shimoni-Livny, L.; Glusker, J. P.; Bock, C. W. Inorg. Chem. 1998, 37, 1853-1867