Observing second-order nonlinear optical properties by symmetry breaking in centrosymmetric furan-containing oligoaryl cyclophandienes

Chemistry - A European Journal

Volumn 15, Issue 47, 2009, Pages 13201-13209

  Lin, Hsin Chieh ^a   Hsu, Jui Hung ^b   Lee, Chao Kuei ^b   Tai, Oliver Yung Hui ^b   Wang, Chin Hsien ^b   Chou, Chih Ming ^a   Chen, Kuang Yen ^a   Wu, Yi Lin ^a   Luh, Tien Yau ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

Cyclophandienes; Nonlinear optics; Oligoaryls; Photochemistry; Symmetry breaking

Indexed keywords

CENTROSYMMETRIC; DOUBLE BONDS; OLIGOARYLS; PHOTOPHYSICAL BEHAVIOR; SECOND-ORDER NONLINEAR OPTICAL; SECOND-ORDER NONLINEAR OPTICAL PROPERTY; STOKES SHIFT; STRUCTURAL FEATURE; SYMMETRY-BREAKING;

OPTICAL MATERIALS; OPTICAL PROPERTIES;

NONLINEAR OPTICS;

EID: 73349098387     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902115     Document Type: Article

References (71)

1. a) Y. Nambu, G. Jona-Lasinio, Phys. Rev. 1961, 122, 345-358;
2. P. G. O. Freund, Y. Nambu, Phys. Rev. Lett. 1964, 12, 714-717;
3. P. G. O. Freund, Y. Nambu, Phys. Rev. Lett. 1964, 13, 221-225;
4. P. G. O. Freund, Y. Nambu, Ann. Phys. 1965, 32, 201-217;
5. M. Kobayashi, H. Kondo, T. Maskawa, Prog. Theor. Phys. 1971, 45, 1955-1959;
6. T. Maskawa, H. Nakajima, Prog. Theor. Phys. 1974, 52, 1326-1354;
7. T. Maskawa, H. Nakajima, Prog. Theor. Phys. 1975, 54, 860-877;
8. T. Inoue, T. Maskawa, Prog. Theor. Phys. 1975, 54, 1833-1847;
9. M. Kobayashi, A. I. Sanda, Phys. Rev. Lett. 1992, 69, 3139-3142.
10. a) R. Stahl, C. Lambert, C. Kaiser, R. Wortmann, R. Jakober, Chem. Eur. J. 2006, 12, 2358-2370;
11. S. Amthor, C. Lambert, S. Dümmler, I. Fischer, J. Schelter, J. Phys. Chem. A 2006, 110, 5204-5214;
12. R. A. Rijkenberg, D. Bebelaar, W. J. Buma, J. Am. Chem. Soc. 2000, 122, 7418-7419;
13. D. Walser, G. Zumofen, T. Plakhotnik, J. Chem. Phys. 2000, 113, 8047-8058;
14. K. Susumu, K. Kunimoto, H. Segawa, T. Shimidzu, J. Photochem. Photobiol. A 1995, 92, 39-46.
15. F. Terenziani, A. Painelli, C. Katan, M. Charlot, M. Blanchard-Desce, J. Am. Chem. Soc. 2006, 128, 15742-15755, and references therein.
16. L. M. Tolbert, X. Zhao, J. Am. Chem. Soc. 1997, 119, 3253-3258.
17. a) E. Hennebicq, C. Deleener, J. L. Brédas, G. D. Scholes, D. Beljonne, J. Chem. Phys. 2006, 125, 054901/1-16;
18. K. F. Wong, M. S. Skaf, C.-Y Yang, P. J. Rossky, B. Bagchi, D. Hu, J. Yu, P. F. Barbara, J. Phys. Chem. B 2001, 105, 6103-6107;
19. S. N. Yaliraki, R. J. Silbey, J. Chem. Phys. 1996, 104, 1245-1253;
20. C. L. Gettinger, A. J. Heeger, J. M. Drake, D. Pine, J. Chem. Phys. 1994, 101, 1673-1678.
21. a) G. de la Torre, P. Vázquez, F. Agulló-López, T. Torres, Chem. Rev. 2004, 104, 3723-3750;
22. ACS Symposium Series 233: Nonlinear Optical Properties of Organic and Polymeric Materials (Ed.: D. J. Williams), ACS, Washington, 1985;
23. G. L. Richmond, J. M. Robinson, V. L. Shannon, Prog. Surf. Sci. 1988, 28, 1-70;
24. Y. R. Shen, Annu. Rev. Phys. Chem. 1989, 40, 327-350;
25. K. B. Eisenthal, Annu. Rev. Phys. Chem. 1992, 43, 627-661.
26. a) B. Koopmans, A.-M. Janner, H. T. Jonkman, G. A. Sawatzky, F. vanderWoude, Phys. Rev. Lett. 1993, 71, 3569-3572;
27. B. Koopmans, A. Anema, H. T. Jonkman, G. A. Sawatzky, F. van der Woude, Phys. Rev. B 1993, 48, 2759-2764;
28. Z. Shuai, J. L. Brédas, Adv. Mater. 1994, 6, 486-488.
29. a) P. Guyot-Sionnest, Y. R. Shen, Phys. Rev. B 1988, 38, 7985-7989;
30. M. Sato, A. Takeuchi, T. Yamada, H. Hoshi, K. Ishikawa, T. Mori, H. Takezoe, Phys. Rev. E 1997, 56, R6264-R6266.
31. a) G. J. Ashwell, Nature 1995, 375, 385-388;
32. K. B. Eisenthal, Chem. Rev. 1996, 96, 1343-1360;
33. J. I. Dadap, J. Shan, K. B. Eisenthal, T. F. Heinz, Phys. Rev. Lett. 1999, 83, 4045-4048;
34. J. Shan, J. I. Dadap, I. Stiopkin, G. A. Reider, T. F. Heinz, Phys. Rev. A 2006, 73, 023819/1-4.
35. S. Kielich, J. R. Lalanne, F. B. Martin, Phys. Rev. Lett. 1971, 26, 1295-1298.
36. S. N. Yaliraki, R. J. Silbey, J. Chem. Phys. 1999, 111, 1561-1568.
37. a) H.-C Lin, W.-Y Lin, H.-T Bai, J.-H. Chen, B.-Y Jin, T.-Y Luh, Angew. Chem. 2007, 119, 915-918;
38. Angew. Chem. Int. Ed. 2007, 46, 897-900;
39. J.-C Tseng, H.-C. Lin, S.-L. Huang, C.-L. Lin, B.-Y. Jin, C.-Y. Chen, J.-K. Yu, P.-T Chou, T.-Y. Luh, Org. Lett. 2003, 5, 4381-4384.
40. a) I. D. L. Albert, T. J. Marks, M. A. Ratner, J. Am. Chem. Soc. 1998, 120, 11174-11181;
41. H. Kang, A. Facchetti, P. Zhu, H. Jiang, Y. Yang, E. Cariati, S. Righetto, R. Ugo, C. Zuccaccia, A. Macchioni, C. L. Stern, Z. Liu, S.-T Ho, T. J. Marks, Angew. Chem. 2005, 117, 8136-8139;
42. Angew. Chem. Int. Ed. 2005, 44, 7922-7925;
43. C. M. Isborn, E. R. Davidson, B. H. Robinson, J. Phys. Chem. A 2006, 110, 7189-7196;
44. D. R. Kanis, M. A. Ratner, T. J. Marks, Chem. Rev. 1994, 94, 195-242;
45. S. Di Bella, G. Lanza, I. Fragalà, S. Yitzchaik, M. A. Ratner, T. J. Marks, J. Am. Chem. Soc. 1997, 119, 3003-3006.
46. a) C.-F. Lee, L.-M. Yang, T.-Y. Hwu, A.-S. Feng, J.-C. Tseng, T.-Y. Luh, J. Am. Chem. Soc. 2000, 122, 4992-4993;
47. C.-F. Lee, C.-Y. Liu, H.-C. Song, S.-J. Luo, J.-C. Tseng, H.-H. Tso, T.-Y. Luh, Chem. Commun. 2002, 2824-2825;
48. C.-M. Chou, W.-Q. Chen, J.-H. Chen, C.-L. Lin, J.-C. Tseng, C.-F. Lee, T.-Y. Luh, Chem. Asian J. 2006, 1, 46-55.
49. For reviews, see: a) T.-Y. Luh, Pure Appl. Chem. 2005, 77, 1213-1219;
50. T.-Y. Luh, C.-F. Lee, Eur. J. Org. Chem. 2005, 3875-3885.
51. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
52. a) J. Cornil, D. A. dos Santos, X. Crispin, R. Silbey, J. L. Brédas, J. Am. Chem. Soc. 1998, 120, 1289-1299;
53. J. Cornil, D. Beljonne, J.-P. Calbert, J.-L. Brédas, Adv. Mater. 2001, 13, 1053-1067.
54. a) J. Zyss, I. Ledoux, Chem. Rev. 1994, 94, 77-105;
55. F. W. Vance, J. T. Hupp, J. Am. Chem. Soc. 1999, 121, 4047-4053.
56. 1 and the bridging olefinic carbon atom was 1.471 Å, that is, shorter than those in trans-or cis-stilbenes (1.481 and 1.489 Å, see: C. J. Finder, M. G. Newton, N. L. Allinger, Acta Crystallogr. Sect. B 1974, 30, 411-415;
57. 3 and 4 showed that the corresponding bond lengths were 1.476 and 1.466 Å, respectively.
58. a) S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, J. Skindhoj, Science 1994, 263, 511-514;
59. S. R. Marder, B. Kippelen, A. K.-Y Jen, N. Peyghambarian, Nature 1997, 388, 845-851;
60. S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G, Bourhill, J.-L. Brédas, B. M. Pierce, Science 1994, 265, 632-635;
61. M. A. Ahlheim, M, Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y Hu, S. R. Marder, J. W. Perry, C. Runser, M. Staehelin, B. Zysset, Science 1996, 271, 335-337;
62. C. Dehu, F. Meyers, E. Hendrickx, K. Clays, A. Persoons, S. R. Marder, J.-L. Bredas, J. Am. Chem. Soc. 1995, 117, 10127-10128;
63. S. R. Marder, C. B. Gorman, B. G. Tiemann, L.-T. Cheng, J. Am. Chem. Soc. 1993, 115, 3006-3007;
64. L.-T. Cheng, W. Tam, S. R. Marder, A. E. Stiegman, G. Rikken, C. W. Spangler, J. Phys. Chem. 1991, 95, 10643-10652.
65. a) S. Brasselet, J. Zyss, J. Opt. Soc. Am. B 1998, 15, 257-288;
66. J. Zyss, J. Chem. Phys. 1993, 98, 6583-6599;
67. O. Maury, H. Le Bozec, Acc. Chem. Res. 2005, 38, 691-704.
68. W. S. Emerson, R. A. Heimsch, J. Am. Chem. Soc. 1951, 73, 1297-1298.
69. T. Bosanac, C. S. Wilcox, Org. Lett. 2004, 6, 2321-2324.
70. O. Y.-H. Tai, C. H. Wang, A. K.-Y. Jen, J. Chem. Phys. 2004, 121, 6086-6092.
71. J. L. Oudar, D. S. Chemla, J. Chem. Phys. 1977, 66, 2664-2668.