Electronic and structural effects on the nonlinear optical behavior in push-pull TTF/tricarbonyl chromiun arene complexes

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 6986-6995

  Insuasty, Braulio ^a,b   Atienza, Carmen ^a   Seoane, Carlos ^a   Martín, Nazario ^a   Garín, Javier ^c   Orduna, Jesús ^c   Alcalá, Rafael ^c   Villacampa, Belén ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD DEL VALLE   (Colombia)

^c CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM COMPOUNDS; DERIVATIVES; ELECTRONIC PROPERTIES; GROUND STATE; OLEFINS; POLARIZATION; PROBABILITY DENSITY FUNCTION;

ELECTRON DONORS; NONLINEAR OPTICAL BEHAVIOR; OLEFINATION REACTION;

ELECTRONS;

CARBONYL DERIVATIVE; CHROMIUM DERIVATIVE; LIGAND; POLYCYCLIC AROMATIC HYDROCARBON; TETRATHIAFULVALENE DERIVATIVE; VINYL DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CONJUGATION; COVALENT BOND; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; DIPOLE; ELECTROCHEMICAL ANALYSIS; HORNER REACTION; HYPERPOLARIZATION; NONLINEAR SYSTEM; OXIDATION; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TIME;

EID: 5444220141     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0493673     Document Type: Article

References (73)

1. (a) Nonlinear Optical Properties of Organic Molecules and Crystals; Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987.
2. (b) Materials for Nonlinear Optics: Chemical Perspectives; Marder, S. R., Sohn, J. E., Stucky, G. D., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1991.
3. (c) Chem. Rev. 1994, 1, 94.
4. (d) Bosshard, C.; Sutter, K.; Pretre, P.; Hulliger, J.; Florsheimer, M.; Kaatz, P.; Gunter, P. Organic Nonlinear Optical Materials; Gordon & Breach: Basel, 1995.
5. (e) Polymers for Second-Order Nonlinear Optics; Lindsay, G. A., Singer, K. D.; Eds.; ACS Symposium Series 601; American Chemical Society: Washington, DC, 1995.
6. (f) Kajzar, F.; Swalen, J. Organic. Thin Films for Waveguiding Nonlinear Optics; Gordon & Breach: Amsterdam, 1996.
7. (g) Miyata, S.; Sasabe, H. Poled Polymers and Their Applications to SHG and EO Devices; Gordon & Breach: Amsterdam, 1997.
8. (h) Nalwa, H. S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, 1997.
9. (i) Kuzyk, M. G.; Singer, K. D.; Twieg, R. J. J. Opt. Soc. Am. B. Ppt. Phys. 1998, 15, 254.
10. See for example: Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 4, 21.
11. For reviews see: (a) Whittal, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291.
12. (b) Di Bella, S. Chem. Soc. Rev. 2001, 30, 355.
13. (a) Coe, B. J.; Houbrechts, S.; Asselberghs, I.; Perssons, A. Angew. Chem., Int. Ed. 1999, 38, 366.
14. (b) Malaun, M.; Reeves, Z. R.; Paul, R. L.; Jeffery, J. C.; McCleverty, J. A.; Ward, M. D.; Asselberghs, I.; Clays, K.; Persoons, A. Chem. Commun. 2001, 49.
15. (a) Khodorkovsky, V.; Becker, J. Y. In Organic Conductors; Farges, J.-P., Ed.; Dekker: New York, 1994; Chapter 3.
16. (b) Fox, J. M.; Katz, T. J.; Elshocht, T. V.; Kauranen, M.; Persons, A.; Thongpanchang, T.; Krauss, T.; Brus, L. J. Am. Chem. Soc. 1999, 121, 3453.
17. (c) Lin, W.; Wang, Z.; Ma, L. J. Am. Chem. Soc. 1999, 121, 3453.
18. (d) Bernard, S.; Yu, P.; Audiere, J. P.; Riviere, E.; Clement, R.; Guilhem, J.; Tchertanov, L.; Nakatani, K. J. Am. Chem. Soc. 2000, 122, 9444.
19. For some recent reviews on TTF, see: (a) Bryce, M. R. Chem. Soc. Rev. 1991, 20, 355.
20. (b) Bryce, M. R. J. Mater. Chem. 1995, 5, 1481.
21. (c) Schukat, G.; Richter, A. M.; Fanghanel, E. Sulfur Rep. 1987, 7, 155.
22. (d) Schukat, G.; Fanghanel, E. Sulfur Rep. 1993, 14, 245.
23. (e) Schukat, G.; Fanghanel, E. Sulfur Rep. 1996, 18, 1.
24. (f) Garín, J. Heterocycl. Chem. 1995, 62, 249.
25. (g) Simonsen, K. B.; Svenstrup, N.; Lau, J.; Simonsen, O.; Mork, P.; Kristensen, G. J.; Becher, J. Synthesis 1996, 407.
26. (h) Otsubo, T.; Aso, Y.; Takimiya, K. Adv. Mater. 1996, 8, 203.
27. (i) Adam, M.; Mullen, K. Adv. Mater. 1994, 6, 439.
28. (j) Becher, J.; Lau, J.; Mork, P. In Electronic Material: The Oligomer Approach; Mullen, K., Wegner, G., Eds.; Wiley-VCH: New York, 1998; pp 198-233.
29. (k) Bryce, M. R.; Davenpot, W.; Goldenberg, L. M.; Wang, C. Chem. Commun. 1998, 945.
30. (l) Jorgensen, T.; Hansen, T. K.; Becher, J. Chem. Soc. Rev. 1994, 41.
31. (m) Simonsen, K. B.; Becher, J. Synlett 1997, 1211.
32. (n) Nielsen, M. B.; Becher, J. Liebigs Ann./Recueil 1997, 2177.
33. (o) Coronado, E.; Gómez-García, C. J. Chem. Rev. 1998, 98, 273.
34. (p) Roncali, J. J. Mater. Chem. 1997, 7, 2307.
35. (q) Day, P.; Kurmoo, M. J. Mater. Chem. 1997, 8, 1291.
36. (r) Bryce, M. R. Adv. Mater. 1999, 11, 11.
37. (s) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153.
38. (t) Bryce, M. R. J. Mater. Chem. 2000, 10, 589.
39. Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372.
40. (a) Andreu, R.; de Lucas, A. I.; Garín, J.; Martín, N.; Orduna, J.; Sánchez, L.; Seoane, C. Synth. Met. 1997, 86, 1817.
41. (b) De Lucas, A. I.; Martín, N.; Sánchez, L.; Seoane, C.; Andreu, R.; Garín, J.; Orduna, J.; Alcalá, R.; Villacampa, B. Tetrahedron 1998, 54, 4655.
42. (c) Garín, J.; Orduna, J.; Rupérez, J. I.; Alcalá, R.; Villacampa, B.; Sánchez, C.; Martín, N.; Segura, J. L.; González, M. Tetrahedron Lett. 1998, 39, 3577.
43. (d) González, M.; Martín, N.; Segura, J. L.; Seoane, C.; Garín, J.; Orduna, J.; Alcalá, R.; Sánchez, C.; Villacampa, B. Tetrahedron Lett. 1999, 40, 8599.
44. (e) Garín, J.; Orduna, J.; Andreu, R. Recent Res. Dev. Org. Chem. 2001, 5, 77.
45. (f) Gonzalez, M.; Segura, J. L.; Seoane, C.; Martín, M.; Garín, J.; Orduna, J.; Alcalá, R.; Villacampa, B.; Hernández, V.; López, J. T. J. Org. Chem. 2001, 66, 8872.
46. Otero, M.; Herranz, M. A.; Seoane, C.; Martín, N.; Garín, J.; Orduna, J.; Alcalá, R.; Villacampa, B. Tetrahedron 2002, 58, 7463 and references therein.
47. (a) Coe, B. J. Chem. Eur. J. 1999, 5, 2464.
48. (b) Paul, F.; Costuas, K.; Ledoux, I.; Devean, S.; Zyss, I.; Halet, J.-F.; Laptine, C. Organometallics 2003, 21, 5229.
49. (a) Boutagy, J.; Thomas, R. Chem. Rev. 1974, 78, 87.
50. (b) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73.
51. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
52. (a) For reviews of nucleophilic additions, see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Elmsford, NY, 1995; Vol. 12, p 979.
53. (b) For ring lithiations, see, e.g.: Semmelhack M. F., In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Elmsford, NY, 1995; Vol. 12, p 1039.
54. (c) For stabilization of chain activation, see, e.g.: Davies, S. G.; Donohoe, T. J. Synlett 1993, 323.
55. Muller, T. J. J. Tetrahedron Lett. 1997, 38, 1025.
56. Gonzalez, M.; Martín, N.; Segura, J. L.; Garín, J.; Orduna, J. Tetrahedron Lett. 1998, 39, 3269.
57. Skabara, P. J.; Bryce, M. R.; Batsanov, A. S.; Howard, J. A. K. J. Org. Chem. 1995, 60, 4644.
58. (a) Gansow, O. A.; Schexnayder, D. A.; Kimura, B. Y. J. Am. Chem. Soc. 1972, 94, 3406.
59. (b) Brown, D. A.; Chester, J. P.; Fitzpatrick, N. J.; King, I. J. Inorg. Chem. 1977, 16, 2497.
60. (c) Hunter, A. D.; Mozol, V.; Tsai, S. D. Organometallics 1992, 11, 2251.
61. Muller, T. J. J. J. Organomet. Chem. 1999, 578, 95.
62. Herranz, M. A.; Martín, N.; Sánchez, L.; Garín, J.; Orduna, J.; Alcalá, R.; Villacampa, B.; Sánchez, C. Tetrahedron 1998, 54, 11651 and references therein.
63. (a) Martín, N.; Sánchez L.; Seoane C.; Ortí E.; Viruela, P. M.; Viruela, R. J. Org. Chem. 1998, 63, 1268.
64. (b) Martín, N.; Ortí, E. Handbook of Advanced Electronic and Photonic Materials and Devices; Academic Press: San Diego 2001; Vol. 3.
65. (a) Yamashita, Y.; Kobayashi, Y.; Miyashi, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 1052.
66. (b) Bryce, M. R.; Moore, A. J.; Hasan, M.; Ashwell, G. J.; Fraser, A. T.; Clegg, W.; Hursthouse, M. B.; Karaulov, A. I. Angew. Chem., Int. Ed. Engl. 1990, 29, 1450.
67. (a) Andreu, R.; Garín, J.; Orduna, J. Tetrahedron 2001, 57, 7883.
68. (b) Pou-Amerigo, R.; Viruela, P. M., Viruela, R.; Rubio, M.; Ortí, E. Chem. Phys. Lett. 2002, 352, 491.
69. (a) Pou-Amerigo, R.; Ortí, E.; Merchán, M.; Rubio, M.; Viruela, P. M. J. Phys. Chem. A 2002, 106, 631.
70. (b) Viruela, R., Viruela, P. M.; Pou-Amerigo, R.; Ortí, E. Synth. Met. 1999, 103, 1991.
71. (a) Kanis D. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 10338.
72. (b) Müller, T. J. J.; Netz, A.; Ansorge, M. Organometallics 1999, 18, 5066.
73. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.01; Gaussian, Inc.: Pittsburgh, PA, 2003.