Redox-switchable second-order molecular polarizabilities with electron-rich iron σ-Aryl acetylides

Organometallics

Volumn 21, Issue 24, 2002, Pages 5229-5235

  Paul, Frédéric ^a   Costuas, Karine ^b   Ledoux, Isabelle ^c   Deveau, Sandrine ^c   Zyss, Joseph ^c   Halet, Jean François ^b   Lapinte, Claude ^a  

^a Campus de Beaulieu ^*  (France)

^b Laboratoire de Chimie du Solide et Inorganique Moleculaire de Rennes   (France)

^c UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; ELECTRON TRANSPORT PROPERTIES; MOLECULAR DYNAMICS; POLARIZATION; REDOX REACTIONS;

MOLECULAR POLARIZABILITIES;

ORGANOMETALLICS;

EID: 0012332565     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020303x     Document Type: Article

References (98)

1. (a) Denis, R.; Toupet, L.; Paul, F.; Lapinte, C. Organometallics 2000, 19, 4240-4251.
2. (b) Paul, F., Mevellec, J.-Y.; Lapinte, C. J. Chem. Soc., Dalton Trans. 2002, 1783-1790.
3. Weyland, T.; Ledoux, I.; Brasselet, S.; Zyss, J.; Lapinte, C. Organometallics 2000, 19, 5235-5237.
4. Manna, J.; John, K. D.; Hopkins, M. D. Adv. Organomet. Chem. 1995, 38, 80-154.
5. (a) Chisholm, M. H. Acc. Chem. Res. 2000, 33, 53-61.
6. (b) Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 35, 1351-1377.
7. (c) Ziessel, R. Synthesis 1999, 1839-1865.
8. (d) Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863-1933.
9. (e) Yam, V. W.-W.; Lo, K. K.-W.; Wong, K. M.-C. J. Organomet. Chem. 1999, 578, 3-30.
10. (f) Bruce, M. I. Chem. Rev. 1998, 98, 2797-2858.
11. (g) Stang, P. J. Chem. Eur. J. 1998, 4, 19-27.
12. (h) Akita, M.; Chung, M.-C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-Oka, Y. Organometallics 1997, 16, 4882-4888.
13. (h) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547-550.
14. (a) Peters, T. B.; Bohling, J. C.; Arif, A. M.; Gladysz, J. A. Organometallics 1999, 18, 3261-3263, and references cited.
15. (b) Touchard, D.; Haquette, P.; Guesmi, S.; Le Pichon, L.; Daridor, A.; Toupet, L.; Dixneuf, P. H. Organometallics 1997, 16, 3640-3648.
16. (c) Markwell, R. D.; Butler, I. S.; Kakkar, A. K.; Khan, M. S.; Al-Zahkawani, Z. H.; Lewis, J. Organometallics 1996, 15, 2331-2337, and references cited.
17. Paul, F.; Lapinte, C. Coord. Chem. Rev. 1998, 178/180, 427-505.
18. Paul, F.; Lapinte, C. In Unusual Structures and Physical Properties in Organometallic Chemistry; Gielen, M., Willem, R., Wrackmeyer, B., Eds.; Wiley & Sons, Ldt: Chichester, 2002; 219-295.
19. (a) Paul, F.; Meyer, W.; Jiao, H.; Toupet, L.; Gladysz, J. A.; Lapinte, C. J. Am. Chem. Soc. 2000, 122, 9405-9414.
20. (b) Weyland, T.; Costuas, K.; Toupet, L.; Halet, J.-F.; Lapinte, C. Organometallics 2000, 19, 4228-4239.
21. (c) Le Stang, S.; Paul, F.; Lapinte, C. Organometallics 2000, 19, 1035-1043.
22. (d) Weyland, T.; Costuas, K.; Mari, A.; Halet, J.-F.; Lapinte, C. Organometallics 1998, 17, 5569-5579.
23. (e) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129-7138.
24. Bruce, M. I.; Low, P. J.; Costuas, K.; Halet, J.-F.; Best, S. P.; Heath, G. H. J. Am. Chem. Soc. 2000, 122, 1949-1962.
25. Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. J. Am. Chem. Soc. 2000, 122, 810-822, and references therein.
26. Kheradmandan, S.; Heinze, K.; Schmalle, H.; Berke, H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2270-2273.
27. Colbert, M. C. C.; Lewis, J.; Long, N. J.; Raithby, P. R.; Younus, M.; White, A. J. P.; Williams, D. J.; Payne, N. J.; Yellowlees, L.; Beljonne, D.; Chawdhury, N.; Friend, R. H. Organometallics 1998, 17, 3034-3043.
28. (a) di Bella, S. Chem. Soc. Rev. 2001, 30, 355-366.
29. (b) Coe, B. J. Chem. Eur. J. 1999, 5, 2464-2471.
30. (c) Whittall, I. R.; MacDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291-362.
31. (d) Whittall, I. R.; MacDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349-322.
32. (e) Hendrickx, E.; Clays, K.; Persoons, A. Acc. Chem. Res. 1998, 31, 675-683.
33. (f) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21-38.
34. (g) Zyss, J. Molecular Nonlinear Optics; Academic Press: New York, 1994.
35. (h) Marder, S. R. In Inorganic Materials; Bruce, D. W., O'Hare, D., Eds.; Wiley & Sons: New York, 1992; pp 115-164.
36. (a) Hurst, S. K.; Cifuentes, M. P.; Morrall, J. P. L.; Lucas, N. T.; Whittal, I. R.; Humphrey, M. G.; Aselberghs, I.; Persoons, A.; Samoc, M.; Luther-Davies, B.; Willis, A. C. Organometallics 2001, 20, 4664-4675.
37. (b) MacDonagh, A. R.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B. Organometallics 1999, 18, 5195-5197.
38. (c) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J.; Asselberghs, I.; Houbrechts, S.; Clays, K.; Persoons, A.; Borge, J.; Garcia-Granda, S. Organometallics 1999, 18, 582-597.
39. (d) MacDonagh, A. R.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B.; Houbrechts, S.; Wada, T.; Sasabe, H.; Persoons, A. J. Am. Chem. Soc. 1999, 121, 1405-1406.
40. (e) Hendrickx, E.; Persoons, A.; Samson, S.; Stephenson, G. R. J. Organomet. Chem. 1997, 542, 295-297.
41. (a) Le Stang, S.; Paul, F.; Lapinte, C. Inorg. Chim. Acta 1999, 291, 403-425.
42. (b) Le Stang, S.; Lenz, D.; Paul, F.; Lapinte, C. J. Organomet. Chem. 1998, 572, 189-192.
43. (a) Oudar, J. L. J. Chem. Phys. 1977, 67, 446-457.
44. (b) Oudar, J. L.; Chemla, D. S. J. Chem. Phys. 1977, 66, 2664-2668.
45. Ledoux, I.; Zyss, J. Chem. Phys. 1982, 73, 203-213.
46. Williams, D. J. Angew. Chem., Int. Ed. Engl. 1984, 23, 690-703.
47. Alain, V.; Blanchard-Desce, M.; Ledoux-Rak, I.; Zyss, J. Chem. Commun. 2000, 353-354.
48. 0 is the wavelength of the incident light (1907 nm).
49. Costuas, K.; Paul, F.; Halet, J.-F.; Lapinte, C. Work in progress.
50. +.
51. Blanch, J. H. J. Chem. Soc. B 1966, 937-938.
52. Jaffé, H. H.; Jones, H. L. Adv. Heterocycl. Chem. 1964, 3, 209-261.
53. March, J. Advanced Organic Chemistry. Reactions, Mechanisms and Structures, 4th ed.; J. Wiley & Sons: New York, 1992.
54. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
55. 1b
56. Ulman, A. J. Chem. Phys. 1988, 92, 2385-2390.
57. Cheng, L.-T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. J. Phys. Chem. 1991, 95, 10631-10643.
58. (a) Sharma, H. K.; Pannell, K. H.; Ledoux, I.; Zyss, J.; Ceccanti, A.; Zannello, P. Organometallics 2000, 19, 770-774.
59. (b) Roberto, D.; Ugo, R.; Bruni, S.; Cariati, E.; Cariati, F.; Fantucci, P. C.; Invernizzi, I.; Quici, S.; Ledoux, I.; Zyss, J. Organometallics 2000, 19, 1775-1788.
60. (c) Hilton, A.; Renouard, T.; Maury, O.; Le Bozec, H.; Ledoux, I.; Zyss, J. Chem. Commun. 1999, 2521-2522.
61. ge. is the energy difference between the ground and excited state.
62. Marder, S. R.; Beratan, D.-N.; Cheng, L.-T. Science 1991, 252, 103-106.
63. Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195-242.
64. Lee, I. S.; Seo, H.; Chung, Y. K. Organometallics 1999, 18, 1091-1096.
65. Dias, R.; Garcia, M. H.; Robalo, M. P.; Green, M. L. H.; Lai, K. K.; Pulham, A. J.; Kuebler, S. M. J. Organomet. Chem. 1993, 453, 241-247.
66. Müller, T. J. J.; Netz, A.; Ansorge, M.; Schmälzlin, E.; Bräuchle, C.; Meerholz, K. Organometallics 1999, 18, 5066-5074.
67. 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.
68. 5 for instance may enhance the pyridyl ring accepting properties. However, for a caveat about the beneficial effect of pyridine complexation, see refs 13, 30a, and 39.
69. Kanis, D. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 8203-8204.
70. (a) Mata, J.; Uriel, S.; Peris, E.; Llusar, R.; Houbrechts, S.; Persoons, A. J. Organomet. Chem. 1998, 562, 197-202.
71. (b) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266-5268.
72. Wu, I.-Y.; Lin, J. T.; Luo, J.; Li, C.-S.; Tsai, C.; Wen, Y. S.; Hsu, C.-C.; Yeh, F.-F.; Liou, S. Organometallics 1998, 17, 2188-2198.
73. Stiegman, A. E.; Graham, E. M.; Perry, K. J.; Kundkar, L. R.; Cheng, L.-T.; Perry, J. W. J. Am. Chem. Soc. 1991, 113, 7658-7666.
74. Delfs, C. D.; Stranger, R.; Humphrey, M. G.; MacDonagh, A. M. J. Organomet. Chem. 2000, 607, 208-212.
75. Wenseleers, W.; Gerbrandij, A. W.; Goovaerts, E.; Garcia, M. H.; Robalo, M. P.; Mendes, P. J.; Rodrigues, J. C.; Dias, R. J. Mater. Chem. 1998, 8, 925-930.
76. Another article making this point was published during the reviewing process of the present contribution. See: Garcia, M. H.; Robalo, M. P.; Dias, A. R.; Duarte, M. T.; Wenseleers W.; Aerts, G.; Govaerts, E.; Cifuentes, M. P.; Hurst, S.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B. Organometallics 2002, 21, 2107-2118.
77. Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heat, G. A.; Bogsanyi, D. Organometallics 1997, 16, 2631-2637.
78. Terhune, R. W.; Maker, P. D.; Savage, C. M. Phys. Rev. Lett. 1965, 14, 681-682.
79. Whittall, I. R.; Humphrey, M. G.; Persoons, A.; Houbrechts, S. Organometallics 1996, 15, 1935-1941.
80. di Bella, S.; Fragala, I.; Marks, T. J.; Ratner, M. A. J. Am. Chem. Soc. 1996, 118, 12747-12751.
81. Coe, B. J.; Houbrechts, S.; Asselberghs, I.; Persoons, A. Angew. Chem., Int. Ed. 1999, 38, 366-368.
82. Malaun, M.; Reeves, Z. R.; Paul, R. L.; Jeffery, J. C.; MacCleverty, J. A.; Ward, M. D.; Asselberghs, I.; Clays, K.; Persoons, A. Chem. Commun. 2001, 49-50.
83. Ellis, B. G.; Paul, F.; Lapinte, C.; Bruce, M. I. Work in progress.
84. Willetts, A.; Rice, J. E.; Burland, D. M.; Shelton, D. P. J. Chem. Phys. 1992, 97, 7590-7599.
85. (a) te Velde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84-98.
86. (b) Boerrigter, P. M.; te Velde, G.; Baerends, E. J. J. Quantum Chem. 1988, 33, 87-113.
87. (a) Baerends, E. J.; Ros, P. J. Quantum Chem. 1978, 812, 169-190.
88. (b) Baerends, E. J.; Ellis, D. E.; Ros, P. J. Chem. Phys. 1973, 2, 41-51.
89. Amsterdam Density Functional (ADF) program; version 2.3; Vrije Universiteit: Amsterdam, The Netherlands, 1996.
90. Vosko, S. D.; Wilk, L.; Nusair, M. Can. J. Chem. 1990, 58, 1200-1211.
91. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
92. (b) Becke, A. D. J. Chem. Phys. 1986, 84, 4524-4529.
93. (a) Perdew, J. P. Phys. Rev. B 1986, 34, 7406.
94. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
95. Verluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322-328.
96. Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heat, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127-137.
97. Naulty, R. H.; Cifuentes, M. P.; Humphrey, M. G.; Houbrechts, S.; Boutton, C.; Persoons, A.; Heath, G. A.; Hockless, D. C. R.; LutherDavies, B.; Samoc, M. J. Chem. Soc., Dalton Trans. 1997, 4167-4174.
98. Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738-5745.