Gold(III) complexes of asymmetrically aryl-substituted 1,2-dithiolene ligands featuring potential-controlled spectroscopic properties: An insight into the electronic properties of bis(Pyren-1-yl-ethylene-1,2-dithiolato)Gold(III)

Chemistry - An Asian Journal

Volumn 6, Issue 1, 2011, Pages 198-208

  Aragoni, M Carla ^a   Arca, Massimiliano ^a   Devillanova, Francesco A ^a   Isaia, Francesco ^a   Lippolis, Vito ^a   Pintus, Anna ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

1,2 dithiolene complexes; density functional calculations; electrochemistry; gold; nonlinear optics

Indexed keywords

CIS AND TRANS ISOMERS; CIS ISOMERS; DENSITY-FUNCTIONAL CALCULATIONS; DFT CALCULATION; DITHIOLENE; ELECTROCHROMICS; HYPER-POLARIZABILITY; NEUTRAL COMPLEXES; NON-LINEAR OPTICAL PROPERTIES; PROMISING MATERIALS; SECOND-ORDER NONLINEAR OPTICAL; SPECTROSCOPIC FEATURES; SPECTROSCOPIC PROPERTY; TETRABUTYLAMMONIUM; TIME-DEPENDENT DFT; VISIBLE EMISSIONS;

ABSORPTION; ABSORPTION SPECTROSCOPY; ARGON; DENSITY FUNCTIONAL THEORY; ELECTROCHEMICAL PROPERTIES; ELECTROCHEMISTRY; ELECTRONIC PROPERTIES; ETHYLENE; GOLD; INFRARED DEVICES; ISOMERS; NONLINEAR OPTICS; OPTICAL MATERIALS; OPTICAL PROPERTIES;

GOLD COMPOUNDS;

EID: 78650777309     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000525     Document Type: Article

References (76)

1. M. Arca, M. C. Aragoni, Ch. 12. 3, in Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium, and Tellurium (Ed.:, F.A. Devillanova,), Royal Society of Chemistry, 2006, 797-830.
2. P. Cassoux, Coord. Chem. Rev. 1999, 185-186, 213-232
3. N. Robertson, L. Cronin, Coord. Chem. Rev. 2002, 227, 93-127
4. S. Dalgleish, N. Robertson, Coord. Chem. Rev. 2010, 254, 1549-1558.
5. C. Faulmann, P. Cassoux, Prog. Inorg. Chem. 2004, 52, 399-489.
6. C. A. Mitsopoulou, Coord. Chem. Rev. 2010, 254, 1448-1456
7. S. Meskaldji, L. Belkhiri, T. Arliguie, M. Fourmigue, M. Ephritikhine, A. Boucekkine, Inorg. Chem. 2010, 49, 3192-3200
8. P. Romaniello, M. C. D'Andria, F. Lelj, J. Chem. Phys. A 2010, 114, 5838-5845.
9. B. Garreu-de-Bonneval, K. I. M.-C. Ching, F. Alary, T.-T. Bui, L. Valade, Coord. Chem. Rev. 2010, 254, 1457-1467.
10. C. L. Beswick, J. A. Schulman, E. I. Stiefel, Prog. Inorg. Chem. 2004, 52, 55-110.
11. M. L. Kirk, R. L. McNaughton, M. E. Helton, Prog. Inorg. Chem. 2004, 52, 111-212.
12. K. Wang, Prog. Inorg. Chem. 2004, 52, 267-314.
13. M. C. Aragoni, M. Arca, M. Caironi, C. Denotti, F. A. Devillanova, E. Grigiotti, F. Isaia, F. Laschi, V. Lippolis, D. Natali, L. Pala, M. Sampietro, P. Zanello, Chem. Commun. 2004, 1882-1883.
14. S. D. Cummings, R. Eisemberg, Prog. Inorg. Chem. 2004, 52, 315-367.
15. S. P. Kaiwar, J. K. Hsu, A. Vodacek, G. Yap, L. M. Liable-Sands, A. L. Rheingold, R. S. Pilato, Inorg. Chem. 1997, 36, 2406-2412
16. S. P. Kaiwar, A. Vodacek, N. V. Blough, R. S. Pilato, J. Am. Chem. Soc. 1997, 119, 3311-3316
17. S. P. Kaiwar, A. Vodacek, N. V. Blough, R. S. Pilato, J. Am. Chem. Soc. 1997, 119, 9211-9214
18. K. A. vanHouten, K. A. Walters, K. S. Schanze, R. S. Pilato, J. Fluoresc. 2000, 10, 35-40
19. R. S. Pilato, K. A. vanHouten, Prog. Inorg. Chem. 2004, 52, 369-397.
20. S. D. Cummings, R. Eisemberg, J. Am. Chem. Soc. 1996, 118, 1949-1960.
21. V. Madhu, S. K. Das, Inorg. Chem. 2006, 45, 10037-10039.
22. S. Kokatam, K. Ray, J. Pap, E. Bill, W. E. Geiger, R. J. LeSuer, P. H. Rieger, T. Weyhermüller, F. Neese, K. Wieghardt, Inorg. Chem. 2007, 46, 1100-1111.
23. R. Perochon, L. Piekara-Sady, W. Junga, R. Clérac, M. Formigué, Dalton Trans. 2009, 3052-3061.
24. G. C. Papavassiliou, G. C. Anyfantis, C. P. Raptopoulou, V. Psycaris, N. Ioannidis, V. Petrouleas, P. Paraskevopoulou, Polyhedron 2009, 28, 3368-3372.
25. C. A. S. Hill, A. Charlton, A. E. Underhill, K. M. A. Malik, M. B. Hursthouse, A. I. Karaulov, S. N. Olivier, S. V. Kershaw, J. Chem. Soc. Dalton Trans. 1985, 588-594.
26. T. Verbiest, S. Houbrechts, M. Kauranen, K. Clays, A. Persoons, J. Mater. Chem. 1997, 7, 2175-2189.
27. E. Cerrada, C. Diaz, M. Laguna, I. Romeo, H. Teruel, N. Urzay, Synth. Met. 2001, 120, 817-818.
28. G. C. Anyfantis, G. C. Papavassiliou, A. Terzis, C. P. Raptopoulou, V. Psycharis, P. Paraskevopoulou, Polyhedron 2010, 29, 969-974.
29. L. Ambrosio, M. C. Aragoni, M. Arca, F. A. Devillanova, M. B. Hursthouse, S. L. Huth, F. Isaia, V. Lippolis, A. Mancini, A. Pintus, Chem. Asian J. 2010, 5, 1395-1406.
30. D. M. D. Leeuw, M. M. J. Simenon, A. R. Brown, R. E. F. Einerhand, Synth. Met. 1997, 87, 53-59.
31. M. La Deda, I. Aiello, A. Grisolia, M. Ghedini, M. Amati, F. Lelj, Dalton Trans. 2006, 330-339.
32. -.
33. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, 2 nded., Wiley-VCH, Weinheim, Germany, 2002
34. F. Neese, Coord. Chem. Rev. 2009, 253, 526-563.
35. M. C. Aragoni, M. Arca, F. Demartin, F. A. Devillanova, F. Lelj, F. Isaia, V. Lippolis, A. Mancini, L. Pala, G. Verani, Eur. J. Inorg. Chem. 2004, 3099-3109
36. M. A. Cinellu, G. Minghetti, F. Cocco, S. Stoccoro, A. Zucca, M. Manassero, M. Arca, Dalton Trans. 2006, 5703-5716
37. C. Gabbiani, A. Casini, l. Messori, A. Guerri, M. A. Cinellu, G. Minghetti, M. Corsini, C. Rosani, P. Zanello, M. Arca, Inorg. Chem. 2008, 47, 2368-2379.
38. C. Adamo, V. Barone, J. Chem. Phys. 1998, 108, 664-675.
39. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577.
40. T. H. Dunning Jr, P. J. Hay, in Methods of Electronic Structure, Theory, Vol.2 (Ed.:, H.F. Schaefer,III,) Plenum Press 1977
41. J. V. Ortiz, P. J. Hay, R. L. Martin, J. Am. Chem. Soc. 1992, 114, 2736-2737.
42. J. Tunney, A. J. Blake, S. E. Davies, J. McMaster, C. Wilson, D. C. Garner, Polyhedron 2006, 25, 591-598.
43. S. Rabaà?a, A. C. Cerdeira, A. I. S. Neves, S. I. G. Dias, C. Mézià?re, I. C. Santos, L. C. J. Pereira, M. Fourmigué, R. T. Henriques, M. Almeida, Polyhedron 2009, 28, 1069-1078.
44. M. D. Ward, J. A. McCleverty, J. Chem. Soc. Dalton Trans. 2002, 275-288
45. K. Ray, T. Petrenko, K. Wieghardt, F. Neese, Dalton Trans. 2007, 1552-1566
46. W. Kaim, B. Schwederski, Coord. Chem. Rev. 2010, 254, 1580-1588.
47. The crystal structures of neutral gold bis(1,2-dithiolene) complexes are those with refcodes JEKGAH, XUYLEY, CUCGAJ, CUCGEN, QOYFUG, FQGEO, FOTHUR, TEYSAS, and WUVSAH. The structures POVYOO and SEDLES, which are CT adducts, have not been considered here. CCDC ConQuest version 5.31 updated Feb. 2010.
48. R. Kirmse, M. Kampf, R.-M. Olk, M. Hildebrand, H. Krautscheid, Z. Anorg. Allg. Chem. 2004, 630, 1433-1436.
49. R. L. Schlupp, A. H. Maki, Inorg. Chem. 1974, 13, 44-51.
50. E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO Version 3.1.
51. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926
52. J. E. Carpenter, F. Weinhold, J. Mol. Struct: THEOCHEM 1988, 169, 41-62.
53. 2- at Mulliken level;-0.195 and-0.240 e at NBO level).
54. K. Ray, T. Weyhermüller, F. Neese, K. Wieghardt, Inorg. Chem. 2005, 44, 5345-5360.
55. With regard to 1, the vertical transition D0âD6 is calculated to occur with an almost negligible oscillator strength (f=0.003). It could be tentatively hypothesized that both the geometry relaxation that occurred during IC processes and the libration of the pyrenyl substituents in solution, which lowers the symmetry of 1, might increase the probability of the transition D6âD0.
56. M. Kasha, Discuss. Faraday Soc. 1950, 9, 14-19.
57. P. J. Mendes, A. J. P. Carvalho, J. P. P. Ramalho, J. Mol. Struct. 2009, 900, 110-117.
58. It is acknowledged that electronic transition energy and hyperpolarizability calculations are very sensitive to the basis sets adopted. In particular, diffuse function augmentation can be crucial for small molecules and for high-lying excitation energies (See Ref.[44]). Here, also in consideration of the large number of atoms of the model compounds, the good agreement between the simulated spectra (Figure10) and experimental UV/Vis spectra (Figure1) can be considered an index of the reliability of the level of theory exploited, which has consequently also been adopted for calculating first static hyperpolarizability.
59. A. Alparone, A. Millefiori, S. Millefiori, Chem. Phys. Lett. 2005, 409, 288-294
60. W. Hieringer, E. J. Baerends, J. Phys. Chem. A 2006, 110, 1014-1021
61. F. D. Vila, D. A. Strubbe, Y. Takimoto, X. Andrade, A. Rubio, S. G. Louie, J. J. Rehn, J. Chem. Phys. 2010, 133, 034111-034121.
62. I. R. Whittall, M. G. Humphrey, Organometallics 1996, 15, 5738-5745.
63. M. G. Humphrey, Gold Bull. 2000, 33, 97-102.
64. S. K. Hurst, M. P. Cifuentes, A. M. McDonagh, M. G. Humphrey, M. Samoc, B. Luther-Davies, I. Asselberghs, A. Persoons, J. Organomet. Chem. 2002, 642, 259-267.
65. G. Yang, Z. Su, C. Qin, Y. Zhao, J. Chem. Phys. 2005, 123, 134302-1-5.
66. S.-L. Sun, C.-S. Qin, Y.-Q. Qiu, G.-C. Yang, Z.-M. Su, J. Organomet. Chem. 2009, 694, 1266-1272.
67. D. M. D. Leeuw, M. M. J. Simenon, A. R. Brown, R. E. F. Einerhand, Synth. Met. 1997, 87, 53-59.
68. Gaussian 03, Revision E.01, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery,Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.
69. Basis sets were obtained from the Basis Set Exchange and the Basis Set EMSL Library
70. D. Feller, J. Comput. Chem. 1996, 17, 1571-1586
71. K. L. Schuchardt, B. T. Didier, T. Elsethagen, L. Sun, V. Gurumoorthi, J. Chase, J. Li, T. L. Windus, J. Chem. Inf. Model. 2007, 47, 1045-1052.
72. M. P. Cifuentes, M. G. Humphrey, J. Organomet. Chem. 2004, 689, 3968-3981.
73. D. A. Kleinman, Phys. Rev. 1962, 126, 1977-1979.
74. Gabedit is a free Graphical User Interface for computational chemistry packages written by Abdul-Rahman Allouche. http://lasim.univ-lyon1.fr/allouche/ gabeditb.
75. G. Schaftenaar, J. H. Noordik, J. Comput.-Aided Mol. Des. 2000, 14, 123-134.
76. N. M. O'boyle, A. L. Tenderholt, K. M. Langner, J. Comput. Chem. 2008, 29, 839-845.