Pyrroline chromophores for electro-optics

Chemistry of Materials

Volumn 18, Issue 13, 2006, Pages 2982-2988

  Jang, Sei Hum ^a   Luo, Jingdong ^a   Tucker, Neil M ^a   Leclercq, Amalia ^b   Zojer, Egbert ^b   Haller, Marnie A ^a   Kim, Tae Dong ^a   Kang, Jae Wook ^a   Firestone, Kimberly ^a   Bale, Denise ^a   Lao, David ^a   Benedict, Jason B ^a   Cohen, Dawn ^a   Kaminsky, Werner ^a   Kahr, Bart ^a   Brédas, Jean Luc ^b   Reid, Philip ^a   Dalton, Larry R ^a   Jen, Alex K Y ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRO-OPTIC (EO) COEFFICIENTS; HYPERPOLARIZABILITY; NONLINEAR OPTICAL (NLO) CHROMOPHORES; TRICYANOPYRROLINE (TCP) ELECTRON ACCEPTORS;

AMORPHOUS FILMS; ELECTROOPTICAL EFFECTS; NONLINEAR OPTICS; POLYCARBONATES; STRUCTURAL ANALYSIS; SYNTHESIS (CHEMICAL);

CHROMOPHORES;

EID: 33746336646     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm052861i     Document Type: Article

References (68)

1. (a) Ma, H.; Jen, A. K,-Y.; Dalton, L. R. Adv. Mater. 2002, 14, 1339.
2. (b) Dalton, L. R.; Steier, W. H.; Robinson, B. H.; Zhang, C.; Ren, A.; Garner, S.; Chen, A.; Londergan, T.; Irwin, L.; Carlson, B.; Fifield, L.; Phelan, G.; Kincaid, C.; Amend, J.; Jen, A. K.-Y. J. Mater. Chem. 1999, 9, 1905.
3. (c) Dalton, L. R. A.; Harper, W.; Wu, B.; Chosn, R.; Laquindanum, J.; Liang, Z.; Hubbel, A.; Xu, C. Adv. Mater. 1995, 7, 519.
4. (d) Shi, Y.; Zhang, C.; Xhang, H.; Bechtel, J. H.; Dalton, L. R.; Robinson, B. H.; Steier, W. H. Science 2000, 288, 119.
5. (a) Robinson, B. H.; Dalton, L. R.; Harper, A. W.; Ren, A.; Wang, F.; Zhang, C.; Todorova, G.; Lee, M.; Aniszfeld, R.; Garner, S.; Chen, A.; Steier, W. H.; Houbrecht, S.; Persoons, A.; Ledoux, I.; Zyss, J.; Jen, A. K.-Y. Chem. Phys. 1999, 245, 35.
6. (b) Ma, H.; Liu, S.; Luo, J.; Suresh, S.; Liu, L.; Kang, S.-H.; Haller, M.; Sassa, T.; Dalton, L. R.; Jen, A. K.-Y. Adv. Funct. Mater. 2002, 12, 565.
7. (c) Luo, J.; Liu, S.; Haller, M.; Liu, L.; Ma, H.; Jen, A. K.-Y. Adv. Mater. 2002, 14, 1763.
8. (d) Luo, J.; Haller, M.; Li, H.; Kim, T.-D.; Jen, A. K.-Y. Adv. Mater. 2003, 15, 1635.
9. (e) Luo, J.; Haller, M.; Ma, H.; Liu, S.; Kim, T.; Tian, Y.; Chen, B.; Jang, S.-H.; Dalton, L. R.; Jen, A. K. J. Phys. Chem. B 2004, 108 (24) 8523.
10. (a) Dalton, L. R.; Harper, A. W.; Ghosn, R.; Steier, W. H.; Ziari, M.; Fetterman, H.; Shi, Y.; Mustacich, R. V.; Jen, A. K.-Y.; Shea, K. J. Chem. Mater. 1995, 7, 1060.
11. (b) Marder, S. R.; Cheng, L. T.; Tiemann, B. G.; Friedli, A. C.; Blanchard-Desce, M.; Perry, J. W.; Skindhoj, J. Science 1994, 263, 511.
12. Marder, S. R.; Gorman, C. B.; Meyers, F.; Perry, I. W.; Bourhill, G.; Bredas, J. L.; Pierce, B. M. Science 1994, 265, 632.
13. (a) Dalton, L. R. Opt. Eng. 2000, 39, 589.
14. (b) He, M. Q.; Leslie, T. M.; Sinicropi, J. A. Chem. Mater. 2002, 14, 4662.
15. (c) He, M. Q.; Leslie, T. M.; Sinicropi, J. A.; Garner, S. M.; Reed, L. D. Chem. Mater. 2002, 14, 4669.
16. (d) Liu, S.; Haller, M.; Ma, H.; Dalton, L. R.; Jang, S.-H.; Jen, A. K.-Y. Adv. Mater. 2003, 15, 603.
17. (a) Breitbeil, F. W.; Schranz, J. L. J. Org. Chem. 1979, 44, 4649.
18. (b) Hennion, G. F.; Watson, E. J. J. Org. Chem. 1958, 23, 658.
19. (a) Fatiadi, A. J. Synthesis 1978, 165.
20. (b) Carboni, R. A.; Coffman, D. D.; Howard, E. G. J. Am. Chem. Soc. 1958, 80, 2838.
21. (a) Villemin, D.; Liao, L. Synth. Commun. 2001, 31, 1771.
22. (b) Zhang, C.; Dalton, L. R.; Oh, M.-C.; Xhang, H.; Steier, W. Chem. Mater. 2001, 13, 3043.
23. Melikian, G.; Rouessac, F. P.; Alexandre, C. Synth. Commun. 1995, 25, 3045. The term "conventional" has been used for the conventional convection heating method relative to microwave-oven-based heating.
24. Gubler, U.; He, M.; Wright, D.; Roh, Y.; Twieg, R.; Moerner, W. E. Adv. Mater. 2002, 14, 313.
25. High reactivity of acceptor 1 toward self-condensation makes the separation of acceptor 1 impractical for styryl TCP chromophores.
26. (a) Carboni, R. A. U.S. Patent 3 013 013, 1961.
27. (b) Hiroyuki, M. Hidenori, I.; Shozi, T. U.S. Patent 4 845 235, 1989.
28. (c) Leslie, S. Helmut, W. U.S. Patent 5 166 128, 1992.
29. (d) Denise, C.; Mark, R. J. Barry, H. M.; Paul, W. U.S. Patent 5 660 598, 1997.
30. (e) The following selected patents were added during a review process as prior art of styryl TCP chromophores: Maeda, S.; Kurose, Y.; Ozawa, T. Jpn. Kokai Tokkyo Koho JP 62 216 794 A2 19 870 924, 1987.
31. Matsumoto, H.; Imai, H.; Tada, S. Ger. Offen. DE 3 716 840, 1987.
32. Matsumoto, H.; Imai, H. Jpn. Kokai Tokkyo Koho JP 05 209 373 A2 19 930 820, 1993.
33. Ootani, K. Jpn. Kokai Tokkyo Koho JP 05 072 670 A2 19930326, 1993.
34. Nishigaki, J.; Yabuki, Y. Jpn. Kokai Tokkyo Koho JP 09 255 883 A2 19 970 930, 1997.
35. A number of reports on TCP chromophores appeared during the rather lengthy preparation period of this manuscript: (a) Firestone, K. A.; Reid, P. J.; Lawson, R.; Jang, S.-H.; Dalton, L. R. Inorg. Chim. Acta 2004, 357, 3957.
36. (b) Dalton, L. R.; Jen, A. K.; Steier, W. H.; Robinson, B. H.; Jang, S.-H.; Clot, O.; Song, H. C.; Kuo, Y. H.; Zhang, C.; Rabiei, P.; Ahn, S. W.; Oh, M. Proc. SPIE-Int. Soc. Opt. Eng. 2004, 5351, 1-15.
37. (c) Dalton, L. R.; Robinson, B. H.; Jen, A. K.; Reid, P. J.; Eichinger, B. E.; Jang, S.-H.; Luo, J.; Liu, S.; Liao, Y.; Firestone, K. A.; Bhatambrekar, N. P.; Bale, D.; Haller, M. A.; Battacharjee, S.; Schendel, J.; Sullivan, P. A. ; Hammond, S.; Buker, N.; Cady, F.; Chen, A.; Steier, W. Proc. SPIE-Int. Soc. Opt. Eng. 2004, 5621, 93-104.
38. (d) Dalton, L. R.; Robinson, B. H.; Jen, A. K.; Reid, P.; Eichinger, B.; Sullivan, P. A.; Akelaitis, A.; Bale, D.; Haller, M. A.; Luo, J.; Liu, S.; Liao, Y.; Firestone, K.; Bhatambrekar, N.; Bhattacharjee, S.; Sinness, J.; Hammond, S.; Bruker, N.; Snoeberger, R.; Lingwood, M.; Rommel, H.; Amend, J.; Jang, S.-H.; Chen, A.; Steier, W. Proc. SPIE-Int. Soc. Opt. Eng. 2005, 5935, 1-12.
39. (e) Jen, A. K.; Luo, J.; Kim, T.; Chen, B.; Jang, S.-H.; Kang, J.; Tucker, N. M.; Hau, S.; Tian, Y.; Ka, J.; Haller, M. A.; Liao, Y.; Robinson, B. ; Dalton, L. R.; Herman, W. Proc. SPIE-Int. Soc. Opt. Eng. 2005, 5935, 49-61.
40. (f) Leclercq, A.; Zojer, E.; Jang, S.-H.; Barlow, S.; Geskin, V.; Jen, A. K.-Y.; Marder, S. R.; Bredas, J. L. J. Chem. Phys. 2006, 124, 044510.
41. (g) Kaneko, A.; Lu, Z.; Wang, H.; Twieg, R. J.; Mao, G.; Singer, K. D.; Kaino, T. Nonlinear Opt., Quantum Opt. 2005, 34, 45.
42. (a) Jen, A. K.-Y.; Rao, V. P.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 90.
43. (b) Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. Tetrahedron Lett. 1993, 34, 1747.
44. Structural modification of NLO chromophores with fluorinated dendrons such as those used in chromophore 4c is known to improve the poling efficiency of composite film by reducing electrostatic dipole-dipole interactions between chromophores. Luo, J.; Ma, H.; Haller, M.; Jen, A. K.-Y.; Barto, R. R. Chem. Commun. 2002, 8, 888.
45. The spectroscopic parametrizations along with the Mataga-Nishimoto electron-repulsion potential were used, as implemented in the ZINDO code. The INDO calculations were coupled to a single-configuration interaction (SCI) scheme, previously proven successful at predicting reliable β values. The 30 highest occupied and 30 lowest unoccupied molecular orbitals were active in the SCI procedure, (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
46. (b) Pople, J. A.; Beveridge, D. L.; Dobosh, P. A. J. Chem. Phys. 1967, 47, 2026.
47. (c) Mataga, N.; Nishimoto, K. Z. Phys. Chem. 1957, 13, 140.
48. (d) Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111.
49. (e) Meyers, F.; Marder, S. R.; Pierce, B. M.; Bredas, J. L. J. Am. Chem. Soc. 1994, 116, 10703.
50. (a) He, M.; Twieg, R. J.; Ostroverkhova, O.; Gubler, U.; Wright, D.; Moerner, W. E. Proc. SPIE-Int. Soc. Opt. Eng. 2002, 4802, 9-20.
51. (b) Willets, K. A.; Ostroverkhova, O.; He, M.; Twieg, R. J.; Moemer, W. E. J. Am. Chem. Soc. 2003, 125, 1174.
52. (a) Zhang, C.; Dalton, L. R.; Oh, M.-C.; Xhang, H.; Steier, W. H. Chem. Mater. 2001, 13, 3043.
53. (b) He, M.; Leslie, T. M.; Sinicropi, J. A.; Garner, S. M.; Reed, L. D. Chem. Mater. 2002, 14, 4669.
54. (c) He, M.; Leslie, T. M.; Sinicropi, J. A. Chem. Mater. 2002, 14, 4662.
55. (d) Paley, M. S.; Harris, J. M.; Looser, H.; Baumert, J. C.; Bjorklund, G. C.; Jundt, D.; Twieg, R. J. J. Org. Chem. 1989, 54, 3774.
56. The geometries of the chromophores were optimized using a semiempirical AM1 method as implemented in the MOPAC 3.1 package. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
57. Orr, J.; Ward, J. F. Mol. Phys. 1971, 20, 513.
58. -30 was used for conversion. Comparison of β for all chromophores at a single excitation wavelength, say 1.9 μm, is not useful because of various resonance effects, resulting from the wide range of spectral windows between chromophores.
59. We thank a reviewer for clarifying that the intermolecular electronic interactions and the poling field on individual molecules cannot be treated independently when we generate an acentric order by applying an external poling field.
60. (a) Würthner, F.; yao, S.; Debaerdemaeker, T.; Wortmann, R. J. Am. Chem. Soc. 2002, 124, 9431.
61. (b) Wortmann, R.; Rosch, U.; Redi-Abshiro, M.; Würthner, F. Angew. Chem., Int. Ed. 2003, 42, 2080.
62. (c) Würthner, F.; Yao, S. Angew. Chem., Int. Ed. 2000, 39, 1987.
63. Teng, C. C.; Man, H. T. Appl. Phys. Lett. 1990, 56, 1734.
64. Zhang, C.; Dalton, L. R.; Oh, M.-C.; Zhang, H.; Steier, W. H. Chem. Mater. 2001, 13, 3043.
65. Staub, K.; Levina, G. A.; Barlow, S.; Kowalczyk, T. C.; Lackritz, H.; Barzoukas, M.; Fort, A.; Marder, S. R. J. Mater. Chem. 2003, 13, 825.
66. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: Oxford, 1980; p 77.
67. Zhang, C.; Wang, C.; Dalton, L. R.; Zhang, H.; Steier, W. H. Macromolecules 2001, 34, 253.
68. As a reviewer suggested, luminescence is a common issue with HRS measurements, But interference from the luminescence of TCP chromophores is not a complication in these measurements. Because we use a spectrograph to disperse the radiation coming from the sample, we can discern the multiphoton-excited fluorescence background from the HRS signal through analysis of the line width. In these experiments, the HRS intensity was sufficiently intense relative to the luminescence background that it could be readily identified and measured.