Photoinduced control over the self-organized orientation of amorphous molecular materials using polarized light

Journal of Physical Chemistry B

Volumn 114, Issue 3, 2010, Pages 1227-1232

  Kawamoto, Masuki ^a   Sassa, Takafumi ^a   Wada, Tatsuo ^a  

^a RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOTROPY; AZOBENZENE; GRAIN BOUNDARIES; IRRADIATION; LIGHT POLARIZATION; MOLECULAR ORIENTATION; THIN FILMS;

AMORPHOUS MOLECULAR MATERIALS; ANISOTROPIC ORIENTATIONS; AZOBENZENE MOIETY; ELLIPTICALLY POLARIZED LIGHT; HIGH EFFICIENCY; INCIDENT LIGHT; LINEARLY POLARIZED LIGHT; PHOTO-INDUCED; PHOTO-IRRADIATION; PHOTOINDUCED ORIENTATION; PHOTOINDUCED POLARIZATION; PHOTORESPONSIVE; POLARIZED LIGHT; RESPONSE TIME; SELF-ORGANIZED; TERMINAL GROUPS;

AMORPHOUS MATERIALS;

EID: 76249087074     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp906625a     Document Type: Article

References (50)

1. Lough, W. J., Wainer, I. W., Eds. Chirality in Natural and Applied Science; Blackwell Science: Oxford, England, 2002.
2. For reviews, see (a) Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 708, 1.
3. (b) Ikeda, T.; Mamiya, J.; Yu, Y. Angew. Chem., Int. Ed. 2007, 46, 506.
4. (c) Yashima, E.; Maeda, K.; Nishimura, T. Chem-Eur. J. 2004, 10, 42.
5. (d) Elemans, J. A. A. W.; Rowan, A. E.; Nolte, R. J. M. J. Mater. Chem. 2003, 13, 2661.
6. (e) Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 700, 3483.
7. (f) Rebek, J., Jr. Ace. Chem. Res. 1999, 32, 278.
8. (g) Feringa, B. L.; van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418.
9. For reviews, see: (a) Natansohn, A.; Rochon, P. Chem. Rev. 2002, 702, 4139.
10. (b) Ichimura, K. Chem. Rev. 2000, 700, 1847, and references therein.
11. Todorov, T.; Nikolova, L.; Tomova, N. Appl. Opt. 1984, 23, 4309.
12. Ikeda, T. J. Mater. Chem. 2003, 13, 2037.
13. For example, (a) Zhang, Q.; Bazuin, C. G.; Barrett, C. J. Chem. Mater. 2008, 20, 29.
14. (b) Okano, K.; Tsutsumi, O.; Shishido, A.; Ikeda, T. J. Am. Chem. Soc. 2006, 728, 15368.
15. (c) Ivanov, M.; Ilieva, D.; Minchev, G.; Petrova, Ts.; Dragostinova, V.; Todorov, T.; Nikolova, L. Appl. Phys. Lett. 2005, 86, 181902.
16. (d) Lachut, B. L.; Maier, S. A.; Atwater, H. A.; de Dood, M. J. A.; Polman, A.; Hagen, R.; Kostromine, S. Adv. Mater. 2004, 16, 1746.
17. (e) Zebger, L; Rutloh, M.; Hoffmann, U.; Stumpe, J.; Siesler, H. W.; Hvilsted, S. J. Phys. Chem. A 2002, 706, 3454.
18. (f) Stracke, A.; Wendorff, J. H.; Mahler, J.; Rafler, G. Macromolecules 2000, 33, 2605.
19. For review, see Choi, S.-W.; Kawauchi, S.; Ha, N. Y.; Takezoe, H. Phys. Chem. Chem. Phys. 2007, 9, 3671, and references therein.
20. (a) Nikolova, L.; Todorov, T.; Andruzzi, F.; Hvilsted, S.; Ramanujam, P. S. Opt. Mater. 1997, 8, 255.
21. (b) Naydenova, I.; Nikolova, L.; Ramanujam, P. S.; Hvilsted, S. J. Opt. A: Pure Appl. Opt. 1999, 7, 439.
22. (c) Ivanov, M.; Naydenova, L.; Todorov, T.; Nikolova, L.; Petrova, T.; Tomova, N.; Dragostinova, V. J. Mod. Opt. 2000, 47, 861.
23. (d) Nikolova, L.; Nedelchev, L.; Todorov, T.; Petrova, Tz.; Tomova, N.; Dragostinova, V.; Ramanujam, P. S.; Hvilsted, S. Appl. Phys. Lett. 2000, 77, 657.
24. (a) Iftime, G.; Labarthet, F. L.; Nathansohn, A.; Rochon, P. J. Am. Chem Soc. 2000, 722, 12646.
25. (b) Hore, D.; Wu, Y.; Natansohn, A.; Rochon, P. J. Appl. Phys. 2003, 94, 2162.
26. (c) Wu, Y.; Natansohn, A.; Rochon, P. Macromolecules 2004, 37, 6801.
27. (a) Choi, S- W.; Kang, S.; Takanishi, Y.; Ishikawa, K.; Watanabe, J.; Takezoe, H. Angew. Chem., Int. Ed. 2006, 45, 6503.
28. (b) Choi, S- W.; Izumi, T.; Hoshino, Y.; Takanishi, Y.; Ishikawa, K.; Watanabe, J.; Takezoe, H. Angew. Chem., Int. Ed. 2006, 45, 1382.
29. (c) Choi, S-. W.; Ha, N. Y.; Shiromo, K.; Rao, N. V. S.; Paul, M. K.; Toyooka, T.; Nishimura, S.; Wu, J. W.; Park, B.; Takanishi, Y.; Ishikawa, K.; Takezoe, H. Phys. Rev. E 2006, 73, 021702.
30. (a) Takaishi, K.; Kawamoto, M.; Tsubaki, K.; Wada, T. J. Org. Chem. 2009, 74, 5723.
31. (b) Kawamoto, M.; Aoki, T.; Shiga, N.; Wada, T. Chem. Mater. 2009,27, 564.
32. (c) Kawamoto, M.; Aoki, T.; Wada, T. Chem. Commun. 2007, 930.
33. (a) Shirota, Y. J. Mater. Chem. 2005, 75, 75.
34. (b) Shirota, Y. J. Mater. Chem. 2001, 70, 1.
35. (c) Nakano, H.; Tanino, T.; Takahashi, T.; Ando, H.; Shirota, Y. J. Mater. Chem. 2008, 78, 242.
36. (d) Tanino, T.; Yoshikawa, S.; Ujike, T.; Nagahama, D.; Moriwaki, K.; Takahashi, T.; Kotani, Y.; Nakano, H.; Shirota, Y. J. Mater. Chem. 2007, 17, 4953.
37. (e) Ueda, H.; Tanino, T.; Ando, H.; Nakano, H.; Shirota, Y. Chem. Lett. 2004, 33, 1152.
38. (f) Ando, H.; Takahashi, T.; Nakano, H.; Shirota, Y. Chem. Lett. 2003, 32, 710.
39. (g) Nakano, H.; Takahashi, T.; Kadota, T.; Shirota, Y. Adv. Mater. 2002, 14, 1157.
40. For example, Delaire, J. A.; Nakatani, K. Chem. Rev. 2000, 700, 1817.
41. Mitsunobu, O. Synthesis 1981, 1.
42. (a) Di Bari, L.; Pescitelli, G.; Salvadoři, P. J. Am. Chem. Soc. 1999, 727, 7998.
43. (b) Di Bari, L.; Pescitelli, G.; Marchetti, F.; Salvadoři, P. J. Am. Chem. Soc. 2000, 722, 6395.
44. Circular Dichroism, Principles and Applications; Bérova, N., Nakanishi, K., Eds, Wiley-VCH: New York, Wiley-VCH: New York, 2000.
45. Natansohn, A.; Rochon, P. In ACS Symposium Series: Photonic and Optoelectronic Polymers; Samson, K. J. W., Jenekhe, A., Eds.; American Chemical Society: Washington, DC, 1997; Vol.672, p 236.
46. Ho, M. S.; Natansohn, A.; Rochon, P. Macromolecules 1995, 28, 6124.
47. The growth of birefringence can be described by a biexponential equation as follows: y = A(l-exp(-f/ti) + B(l-exp(-ř/r2)). The fitted parameters obtained are summarized in Table Sl. It is tempting to speculate that photoinduced behavior results from two processes, fast-ci's isomerization and slower reorientation of azobenzene moieties, which is similar to that reported in amorphous polymers containing DRl moieties in ref 18. However, we think the growth of birefringence cannot simply be interpreted in terms of photochemical and reorientation processes, because it includes the effects of changes in aggregation of the azobenzene moieties and/or in the free volume of the local distribution around the chromophores during excitation.
48. A negative value of cp indicates a left-handed polarization rotation.
49. Sumimura, H.; Fukuda, T.; Kim, J. Y.; Barada, D.; Itoh, M.; Yatagai, T. Jpn. J. Appl. Phys. 2006, 45, 451.
50. According to the results of MOPAC, the dihedral angles of the materials are about 90°.