Quantum-chemical investigation of second-order nonlinear optical chromophores: Comparison of strong nitrile-based acceptor end groups and role of auxiliary donors and acceptors

Journal of Chemical Physics

Volumn 124, Issue 4, 2006, Pages

  Leclercq, A ^a   Zojer, E ^a   Jang, S H ^b   Barlow, S ^a   Geskin, V ^c   Jen, A K Y ^b   Marder, S R ^a   Brdas J L ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b University of Washington   (United States)

^c UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AUXILIARY DONORS; HETEROCYCLIC ACCEPTORS; NONLINEAR OPTICAL CHROMOPHORES;

CHROMOPHORES; ELECTROOPTICAL EFFECTS; LIGHT ABSORPTION; NITRILE RESINS; STRUCTURE (COMPOSITION); TELECOMMUNICATION;

QUANTUM THEORY;

EID: 31544436926     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.2155385     Document Type: Article

References (42)

1. Nonlinear Optical Properties of Organic Molecules and Crystals, edited by, D. S. Chemla, and, J. Zyss, (Academic, New York, 1987); Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, edited by, J. L. Bredas, and, R. R. Chance, (Kluwer, Dordrecht, 1990); Materials for Nonlinear Optics, edited by, S. R. Marder, J. E. Sohn, and, G. D. Stucky, (ACS, Washington, 1991); P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers (Wiley, New York, 1991); D. R. Kanis, M. A. Ratner, and T. J. Marks, Chem. Rev. (Washington, D.C.) 94, 195 (1994).
2. Nonlinear Optical Properties of Organic Molecules and Crystals, edited by, D. S. Chemla, and, J. Zyss, (Academic, New York, 1987); Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, edited by, J. L. Bredas, and, R. R. Chance, (Kluwer, Dordrecht, 1990); Materials for Nonlinear Optics, edited by, S. R. Marder, J. E. Sohn, and, G. D. Stucky, (ACS, Washington, 1991); P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers (Wiley, New York, 1991); D. R. Kanis, M. A. Ratner, and T. J. Marks, Chem. Rev. (Washington, D.C.) 94, 195 (1994).
3. Nonlinear Optical Properties of Organic Molecules and Crystals, edited by, D. S. Chemla, and, J. Zyss, (Academic, New York, 1987); Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, edited by, J. L. Bredas, and, R. R. Chance, (Kluwer, Dordrecht, 1990); Materials for Nonlinear Optics, edited by, S. R. Marder, J. E. Sohn, and, G. D. Stucky, (ACS, Washington, 1991); P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers (Wiley, New York, 1991); D. R. Kanis, M. A. Ratner, and T. J. Marks, Chem. Rev. (Washington, D.C.) 94, 195 (1994).
4. Nonlinear Optical Properties of Organic Molecules and Crystals, edited by, D. S. Chemla, and, J. Zyss, (Academic, New York, 1987); Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, edited by, J. L. Bredas, and, R. R. Chance, (Kluwer, Dordrecht, 1990); Materials for Nonlinear Optics, edited by, S. R. Marder, J. E. Sohn, and, G. D. Stucky, (ACS, Washington, 1991); P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers (Wiley, New York, 1991); D. R. Kanis, M. A. Ratner, and T. J. Marks, Chem. Rev. (Washington, D.C.) 94, 195 (1994).
5. Nonlinear Optical Properties of Organic Molecules and Crystals, edited by, D. S. Chemla, and, J. Zyss, (Academic, New York, 1987); Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics, edited by, J. L. Bredas, and, R. R. Chance, (Kluwer, Dordrecht, 1990); Materials for Nonlinear Optics, edited by, S. R. Marder, J. E. Sohn, and, G. D. Stucky, (ACS, Washington, 1991); P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers (Wiley, New York, 1991); D. R. Kanis, M. A. Ratner, and T. J. Marks, Chem. Rev. (Washington, D.C.) 94, 195 (1994).
6. M. Eich, G. C. Bjorklund, and D. Y. Yoon, Polym. Adv. Technol. 1042-7147 10.1002/pat.1990.220010208 1, 189 (1990); D. M. Burland, R. D. Miller, and C. A. Walsh, Chem. Rev. (Washington, D.C.) 94, 31 (1994).
7. M. Eich, G. C. Bjorklund, and D. Y. Yoon, Polym. Adv. Technol. 1042-7147 10.1002/pat.1990.220010208 1, 189 (1990); D. M. Burland, R. D. Miller, and C. A. Walsh, Chem. Rev. (Washington, D.C.) 94, 31 (1994).
8. S. R. Marder, D. N. Beratan, and L. T. Cheng, Science 0036-8075 252, 103 (1991); S. R. Marder, L. T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhoj, Science 0036-8075 263, 511 (1994); S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bŕdas, and B. M. Pierce, Science 0036-8075 265, 632 (1994); L. R. Dalton, A. W. Harper, R. Ghosn, W. H. Steier, M. Ziari, H. Fetterman, Y. Shi, R. V. Mustacich, A. K.-Y. Jen, and K. J. Shea, Chem. Mater. 7, 1060 (1995).
9. S. R. Marder, D. N. Beratan, and L. T. Cheng, Science 0036-8075 252, 103 (1991); S. R. Marder, L. T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhoj, Science 0036-8075 263, 511 (1994); S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bŕdas, and B. M. Pierce, Science 0036-8075 265, 632 (1994); L. R. Dalton, A. W. Harper, R. Ghosn, W. H. Steier, M. Ziari, H. Fetterman, Y. Shi, R. V. Mustacich, A. K.-Y. Jen, and K. J. Shea, Chem. Mater. 7, 1060 (1995).
10. S. R. Marder, D. N. Beratan, and L. T. Cheng, Science 0036-8075 252, 103 (1991); S. R. Marder, L. T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhoj, Science 0036-8075 263, 511 (1994); S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bŕdas, and B. M. Pierce, Science 0036-8075 265, 632 (1994); L. R. Dalton, A. W. Harper, R. Ghosn, W. H. Steier, M. Ziari, H. Fetterman, Y. Shi, R. V. Mustacich, A. K.-Y. Jen, and K. J. Shea, Chem. Mater. 7, 1060 (1995).
11. S. R. Marder, D. N. Beratan, and L. T. Cheng, Science 0036-8075 252, 103 (1991); S. R. Marder, L. T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhoj, Science 0036-8075 263, 511 (1994); S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J. L. Bŕdas, and B. M. Pierce, Science 0036-8075 265, 632 (1994); L. R. Dalton, A. W. Harper, R. Ghosn, W. H. Steier, M. Ziari, H. Fetterman, Y. Shi, R. V. Mustacich, A. K.-Y. Jen, and K. J. Shea, Chem. Mater. 7, 1060 (1995).
12. H. Kang, P. Zhu, Y. Yang, A. Facchetti, and T. J. Marks, J. Am. Chem. Soc. 126, 15974 (2004).
13. M. He, T. M. Leslie, and J. A. Sinicropi, Chem. Mater. 0897-4756 14, 4662 (2002); S. Liu, M. A. Haller, H. Ma, L. R. Dalton, S. H. Jang, and A. K.-Y. Jen, Adv. Mater. (Weinheim, Ger.) 0935-9648 15, 603 (2003); Y. Liao, B. E. Eichinger, K. A. Firestone, J. Am. Chem. Soc. 127, 2758 (2005).
14. M. He, T. M. Leslie, and J. A. Sinicropi, Chem. Mater. 0897-4756 14, 4662 (2002); S. Liu, M. A. Haller, H. Ma, L. R. Dalton, S. H. Jang, and A. K.-Y. Jen, Adv. Mater. (Weinheim, Ger.) 0935-9648 15, 603 (2003); Y. Liao, B. E. Eichinger, K. A. Firestone, J. Am. Chem. Soc. 127, 2758 (2005).
15. M. He, T. M. Leslie, and J. A. Sinicropi, Chem. Mater. 0897-4756 14, 4662 (2002); S. Liu, M. A. Haller, H. Ma, L. R. Dalton, S. H. Jang, and A. K.-Y. Jen, Adv. Mater. (Weinheim, Ger.) 0935-9648 15, 603 (2003); Y. Liao, B. E. Eichinger, K. A. Firestone, J. Am. Chem. Soc. 127, 2758 (2005).
16. B. H. Robinson, L. R. Dalton, A. W. Harper, Chem. Phys. 245, 35 (1999).
17. E. Gudriniece, P. Pastors, and A. Levins, Dokl. Akad. Nauk SSSR 0002-3264 204, 874 (1972); J. M. Raimundo, P. Blanchard, I. Ledoux-Rak, R. Hierle, L. Michaux, and J. Roncali, Chem. Commun. (Cambridge) 1359-7345 2000, 1597; J. M. Raimundo, P. Blanchard, P. Frere, N. Mercier, I. Ledoux-Rak, R. Hierle, and J. Roncali, Tetrahedron Lett. 0040-4039 42, 1507 (2001); Z. Y. Hu, A. Fort, M. Barzoukas, A. K. K.-Y. Jen, S. Barlow, and S. R. Marder, J. Phys. Chem. B 108, 8626 (2004).
18. E. Gudriniece, P. Pastors, and A. Levins, Dokl. Akad. Nauk SSSR 0002-3264 204, 874 (1972); J. M. Raimundo, P. Blanchard, I. Ledoux-Rak, R. Hierle, L. Michaux, and J. Roncali, Chem. Commun. (Cambridge) 1359-7345 2000, 1597; J. M. Raimundo, P. Blanchard, P. Frere, N. Mercier, I. Ledoux-Rak, R. Hierle, and J. Roncali, Tetrahedron Lett. 0040-4039 42, 1507 (2001); Z. Y. Hu, A. Fort, M. Barzoukas, A. K. K.-Y. Jen, S. Barlow, and S. R. Marder, J. Phys. Chem. B 108, 8626 (2004).
19. E. Gudriniece, P. Pastors, and A. Levins, Dokl. Akad. Nauk SSSR 0002-3264 204, 874 (1972); J. M. Raimundo, P. Blanchard, I. Ledoux-Rak, R. Hierle, L. Michaux, and J. Roncali, Chem. Commun. (Cambridge) 1359-7345 2000, 1597; J. M. Raimundo, P. Blanchard, P. Frere, N. Mercier, I. Ledoux-Rak, R. Hierle, and J. Roncali, Tetrahedron Lett. 0040-4039 42, 1507 (2001); Z. Y. Hu, A. Fort, M. Barzoukas, A. K. K.-Y. Jen, S. Barlow, and S. R. Marder, J. Phys. Chem. B 108, 8626 (2004).
20. E. Gudriniece, P. Pastors, and A. Levins, Dokl. Akad. Nauk SSSR 0002-3264 204, 874 (1972); J. M. Raimundo, P. Blanchard, I. Ledoux-Rak, R. Hierle, L. Michaux, and J. Roncali, Chem. Commun. (Cambridge) 1359-7345 2000, 1597; J. M. Raimundo, P. Blanchard, P. Frere, N. Mercier, I. Ledoux-Rak, R. Hierle, and J. Roncali, Tetrahedron Lett. 0040-4039 42, 1507 (2001); Z. Y. Hu, A. Fort, M. Barzoukas, A. K. K.-Y. Jen, S. Barlow, and S. R. Marder, J. Phys. Chem. B 108, 8626 (2004).
21. W. J. Middleton and V. A. Engelhardt, J. Am. Chem. Soc. 0002-7863 80, 2788 (1958); I. T. Suydam and S. G. Boxer, Biochemistry 42, 12050 (2003).
22. W. J. Middleton and V. A. Engelhardt, J. Am. Chem. Soc. 0002-7863 80, 2788 (1958); I. T. Suydam and S. G. Boxer, Biochemistry 42, 12050 (2003).
23. P. R. Varanasi, A. K.-Y. Jen, J. Chandrasekhar, I. N. N. Namboothiri, and A. Rathna, J. Am. Chem. Soc. 0002-7863 10.1021/ja960136q 118, 12443 (1996); I. D. L. Albert, T. J. Marks, and M. A. Ratner, J. Am. Chem. Soc. 0002-7863 10.1021/ja962968u 119, 6575 (1997); C. F. Shu and Y. K. Wang, J. Mater. Chem. 0959-9428 8, 833 (1998); E. Breitung, C. F. Shu, and R. J. MacMahon, J. Am. Chem. Soc. 122, 1154 (2000).
24. P. R. Varanasi, A. K.-Y. Jen, J. Chandrasekhar, I. N. N. Namboothiri, and A. Rathna, J. Am. Chem. Soc. 0002-7863 10.1021/ja960136q 118, 12443 (1996); I. D. L. Albert, T. J. Marks, and M. A. Ratner, J. Am. Chem. Soc. 0002-7863 10.1021/ja962968u 119, 6575 (1997); C. F. Shu and Y. K. Wang, J. Mater. Chem. 0959-9428 8, 833 (1998); E. Breitung, C. F. Shu, and R. J. MacMahon, J. Am. Chem. Soc. 122, 1154 (2000).
25. P. R. Varanasi, A. K.-Y. Jen, J. Chandrasekhar, I. N. N. Namboothiri, and A. Rathna, J. Am. Chem. Soc. 0002-7863 10.1021/ja960136q 118, 12443 (1996); I. D. L. Albert, T. J. Marks, and M. A. Ratner, J. Am. Chem. Soc. 0002-7863 10.1021/ja962968u 119, 6575 (1997); C. F. Shu and Y. K. Wang, J. Mater. Chem. 0959-9428 8, 833 (1998); E. Breitung, C. F. Shu, and R. J. MacMahon, J. Am. Chem. Soc. 122, 1154 (2000).
26. P. R. Varanasi, A. K.-Y. Jen, J. Chandrasekhar, I. N. N. Namboothiri, and A. Rathna, J. Am. Chem. Soc. 0002-7863 10.1021/ja960136q 118, 12443 (1996); I. D. L. Albert, T. J. Marks, and M. A. Ratner, J. Am. Chem. Soc. 0002-7863 10.1021/ja962968u 119, 6575 (1997); C. F. Shu and Y. K. Wang, J. Mater. Chem. 0959-9428 8, 833 (1998); E. Breitung, C. F. Shu, and R. J. MacMahon, J. Am. Chem. Soc. 122, 1154 (2000).
27. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc. 107, 3902 (1985).
28. J. A. Pople, D. L. Beveridge, and P. A. Dobosh, J. Chem. Phys. 47, 2026 (1967).
29. N. Mataga and K. Nishimoto, Z. Phys. Chem. 13, 140 (1957).
30. J. Orr and J. F. Ward, Mol. Phys. 20, 513 (1971).
31. J. L. Oudar and D. S. Chemla, J. Chem. Phys. 0021-9606 10.1063/1.434213 66, 2664 (1977); J. L. Oudar, J. Chem. Phys. 67, 446 (1977).
32. J. L. Oudar and D. S. Chemla, J. Chem. Phys. 0021-9606 10.1063/1.434213 66, 2664 (1977); J. L. Oudar, J. Chem. Phys. 67, 446 (1977).
33. H. D. Cohen and C. C. J. Roothaan, J. Chem. Phys. 43, 34 (1965).
34. P. Chopra, L. Carlacci, H. F. King, and P. N. Prasad, J. Phys. Chem. 93, 7120 (1989).
35. M. N. Nakano, I. Shigemoto, S. Yamada, and K. Yamaguchi, J. Chem. Phys. 103, 4175 (1995).
36. V. M. Geskin and J. L. Bŕdas, J. Chem. Phys. 0021-9606 10.1063/1.477244 109, 6163 (1998); V. M. Geskin, C. Lambert, and J. L. Bŕdas, J. Am. Chem. Soc. 125, 15651 (2003).
37. V. M. Geskin and J. L. Bŕdas, J. Chem. Phys. 0021-9606 10.1063/1.477244 109, 6163 (1998); V. M. Geskin, C. Lambert, and J. L. Bŕdas, J. Am. Chem. Soc. 125, 15651 (2003).
38. M. Halik, W. Wenseleers, C. Grasso, F. Stellacci, E. Zojer, S. Barlow, J. L. Bŕdas, J. W. Perry, and S. R. Marder, Chem. Commun. (Cambridge) 1359-7345 2003, 1490; E. Zojer, W. Wenseleers, M. Halik, C. Grasso, S. Barlow, J. W. Perry, S. R. Marder, and J. L. Bŕdas, ChemPhysChem 5, 982 (2004).
39. M. Halik, W. Wenseleers, C. Grasso, F. Stellacci, E. Zojer, S. Barlow, J. L. Bŕdas, J. W. Perry, and S. R. Marder, Chem. Commun. (Cambridge) 1359-7345 2003, 1490; E. Zojer, W. Wenseleers, M. Halik, C. Grasso, S. Barlow, J. W. Perry, S. R. Marder, and J. L. Bŕdas, ChemPhysChem 5, 982 (2004).
40. B. Domercq, C. Grasso, J. L. Maldonado, M. Halik, S. Barlow, S. R. Marder, and B. Kippelen, J. Phys. Chem. B 1089-5647 10.1021/jp036779r 108, 8647 (2004); C. Risko, E. Zojer, P. Brocorens, S. R. Marder, and J. L. Bŕdas, Chem. Phys. 313, 151 (2005).
41. B. Domercq, C. Grasso, J. L. Maldonado, M. Halik, S. Barlow, S. R. Marder, and B. Kippelen, J. Phys. Chem. B 1089-5647 10.1021/jp036779r 108, 8647 (2004); C. Risko, E. Zojer, P. Brocorens, S. R. Marder, and J. L. Bŕdas, Chem. Phys. 313, 151 (2005).
42. D. Jacquemin, D. Beljonne, B. Champagne, V. M. Geskin, J. L. Bŕdas, and J. M. Andre, J. Chem. Phys. 115, 6766 (2001).