Using end groups to tune the linear and nonlinear optical properties of bis(dioxaborine)-terminated polymethine dyes

ChemPhysChem

Volumn 11, Issue 1, 2010, Pages 130-138

  Matichak, Jonathan D ^a   Hales, Joel M ^a   Ohira, Shino ^a   Barlow, Stephen ^a   Jang, Sei Hum ^b   Jen, Alex K Y ^a   Brédas, Jean Luc ^a   Perry, Joseph W ^a   Marder, Seth R ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Cyanines; Dioxaborine; Nonlinear optics; Polymethinesl Two photon absorption

Indexed keywords

ABSORPTION SPECTROSCOPY; AZO DYES; DIPOLE MOMENT; DYES; EXCITED STATES; GROUND STATE; OPTICAL PROPERTIES; TWO PHOTON PROCESSES;

ABSORPTION MAXIMA; CYANINES; DIOXABORINE; LINEAR AND NONLINEAR OPTICAL PROPERTIES; PENTAMETHINE DYES; TRANSITION DIPOLE MOMENTS; TWO PHOTON ABSORPTION; Z-SCAN MEASUREMENT;

NONLINEAR OPTICS;

EID: 77953415014     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.200900635     Document Type: Article

References (46)

1. G. I. Stegeman, in Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata), CRC Press, Boca Raton, 1997.
2. J. M. Hales, J. W. Perry, in Introduction to Organic Electronic and Optoelectronic Materials and Devices (Eds.: S.-S. Sun, L. Dalton), CRC Press, Orlando, 2008, pp. 521-579.
3. J. L. Brédas, C. Adant, O. Tackx, A. Persoons, B. M. Pierce, Chem. Rev. 1994, 94, 243-278.
4. S. R. Marder, J. W. Perry, G. Bourhill, C. B. Gorman, B. G. Tiemann, K. Mansour, Science 1993, 261, 186-189.
5. F. Meyers, S. R. Marder, B. M. Pierce, J. L. Brédas, J. Am. Chem. Soc. 1994, 116, 10703-10714.
6. S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J.-L. Brédas, B. M. Pierce, Science 1994, 265, 632-635.
7. S. Matsumoto, K. Kubodera, T. Kurihara, T. Kaino, Optics Commun. 1990, 76, 147-150.
8. J. M. Hales, S. Zheng, S. Barlow, S. R. Marder, J. W. Perry, J. Am. Chem. Soc. 2006, 128, 11362-11363.
9. T. Johr, W. Werncke, M. Pfeiffer, A. Lau, L. Dähne, Chem. Phys. Lett. 1995, 246, 521-526.
10. W. Werncke, M. Pfeiffer, T. Johr, A. Lau, W. Grahn, H.-H. Johannes, L. Dähne, Chem. Phys. 1997, 216, 337-347.
11. C. Kuhn, Synth. Met. 1991, 43, 3681-3688.
12. J. S. Craw, J. R. Reimers, G. B. Bacskay, A. T. Wong, N. S. Hush, Chem. Phys. 1992, 167, 77-99.
13. L. M. Tolbert, M. E. Ogle, Synth. Met. 1992, 51, 391-396.
14. C. B. Gorman, S. R. Marder, Chem. Mater. 1995, 7, 215-220.
15. R. S. Lepkowicz, O. V. Przhonska, J. M. Hales, J. Fu, D. J. Hagan, E. W. Van Stryland, M. V. Bondar, Y. L. Slominsky, A. D. Kachkovski, Chem. Phys. 2004, 305, 259-270.
16. L. M. Tolbert, X. Zhao, J. Am. Chem. Soc. 1997, 119, 3253-3258.
17. S. Barlow, L. M. Henling, M. W. Day, S. R. Marder, Chem. Commun. 1999, 1567-1568.
18. S. Barlow, L. M. Henling, M. W. Day, W. P. Schaefer, J. C. Green, T. Hascall, S. R. Marder, J. Am. Chem. Soc. 2002, 124, 6285-6296.
19. K. B. Simonsen, T. Geisler, J. C. Petersen, J. Arentoft, P. Sommer-Larsen, D. R. Greve, C. Jakobsen, J. Becher, M. Malagoli, J. L. Bredas, T. Bjornholm, Eur. J. Org. Chem. 1998, 2747-2757.
20. F. Terenziani, A. Painelli, C. Katan, M. Charlot, M. Blanchard-Desce, J. Am. Chem. Soc. 2006, 128, 15742-15755.
21. G. Görlitz, H. Hartmann, Heteroat. Chem. 1997, 8, 147-155.
22. V. S. Markin, P. I. Abramenko, I. I. Boiko, Zh. Vses. Khim. Obsh. 1984, 29, 457-459.
23. S. Barlow, H. E. Bunting, C. Ringham, J. C. Green, G. U. Bublitz, S. G. Boxer, J. W. Perry, S. R. Marder, J. Am. Chem. Soc. 1999, 121, 3715-3723.
24. M. Halik, H. Hartmann, Chem. Eur. J. 1999, 5, 2511-2517.
25. UV/Vis plots with various concentrations did not show any dependence upon concentration. The most likely explanation for the broadened spectra is a different vibronic structure.
26. J. Ridley, M. Zerner, Theor. Chim. Acta 1973, 32, 111-134.
27. J. A. Pople, D. L. Beveridge, P. A. Dobosh, J. Chem. Phys. 1967, 47, 2026-2033.
28. S. Ohira, I. Rudra, K. Schmidt, S. Barlow, S.-J. Chung, Q. Zhang, J. Matichak, S. R. Marder, J. L. Brédas, Chem. Eur. J. 2008, 14, 11082-11091.
29. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100.
30. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
31. P. A. M. Dirac, Proc. R. Soc. Lond. A 1929, 123, 714-733.
32. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
33. J. C. Slater, Phys. Rev. 1951, 81, 385-390.
34. R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165-169.
35. K. J. Thorley, J. M. Hales, H. L. Anderson, J. W. Perry, Angew. Chem. 2008, 120, 7203-7206.
36. K. J. Thorley, J. M. Hales, H. L. Anderson, J. W. Perry, Angew. Chem. Int. Ed. 2008, 47, 7095-7098.
37. M. Sheik-bahae, A. A. Said, E. W. Van Stryland, Opt. Lett. 1989, 14, 955-957.
38. C. W. Dirk, L.-T. Cheng, M. G. Kuzyk, Int. J. Quantum Chem. 1992, 43, 27-36.
39. E. Zojer, D. Beljonne, T. Kogej, H. Vogel, S. R. Marder, J. W. Perry, J. L. Brédas, J. Chem. Phys. 2002, 116, 3646-3658.
40. J. Fu, L. A. Padilha, D. J. Hagan, E. W. Van Stryland, J. Opt. Soc. Am. B 2007, 24, 56-66.
41. G. I. Stegeman, R. H. Stolen, J. Opt. Soc. Am. B 1989, 6, 652-662.
42. V. Mizrahi, K. W. DeLong, G. I. Stegeman, Opt. Lett. 1989, 14, 1140-1142.
43. 4 to avoid possible hazards caused by using perchlorate salts.
44. A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518-1520.
45. Trans-4-acetylstilbene was synthesized using similar Heck coupling conditions as reported in S. Barlow, C. Risko, S.-J. Chung, N. M. Tucker, V. Coropceanu, S. C. Jones, Z. Levi, J. L. Brédas, S. R. Marder, J. Am. Chem. Soc. 2005, 127, 16900-16911.
46. 1H NMR spectrum was consistent with that reported by R. K. Arvela, N. E. Leadbeater, J. Org. Chem. 2005, 70, 1786-1790.