Photochromism of dithienylethenes containing fluorinated thiophene rings

European Journal of Organic Chemistry

Volumn , Issue 1, 2004, Pages 91-97

  Higashiguchi, Kenji ^a,b   Matsuda, Kenji ^b   Asano, Yukako ^c   Murakami, Akinori ^c   Nakamura, Shinichiro ^c   Irie, Masahiro ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c MITSUBISHI CHEMICAL CORPORATION   (Japan)

Author keywords

Density functional calculations; Diarylethenes; Fluorine; Photochromism; UV Vis spectroscopy

Indexed keywords

1,2 BIS(2 FLUORO 3 THIENYL)PERFLUOROCYCLOPENTENE; 1,2 BIS(5 FLUORO 2 METHYL 3 THIENYL)PERFLUOROCYCLOPENTENE; BIS(3 THIENYL)PERFLUOROCYCLOPENTENE; DITHIENYLETHENE DERIVATIVE; ETHYLENE DERIVATIVE; FLUORINE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; COLOR; DENSITY FUNCTIONAL THEORY; ISOMER; ISOMERIZATION; LIGHT; LIGHT ABSORPTION; PHOTOCHROMISM; QUANTUM YIELD; REACTION ANALYSIS; REPRODUCIBILITY; STRUCTURE ANALYSIS; SYNTHESIS; THERMOSTABILITY;

EID: 11844297382     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400441     Document Type: Article

References (47)

1. [1a] Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2001.
2. [1b] G. H. Brown, Photochromism, Wiley-Interscience. New York, 1971.
3. [1c] H. Dürr, H. Bouas-Laurent, Photochromism: Molecules and Systems, Elsevier, Amsterdam, 2003.
4. [1d] H. Bouas-Laurent, H. Dürr, Pure Appl. Chem. 2001, 73, 639-665.
5. [2a] C. B. McArdle, Applied Photochromic Polymer Systems, Blackie, Glasgow, 1992.
6. [2b] J. C. Crano, R. J. Guglielmetti, Organic Photochromic and Thermochromic Compounds, Plenum Press, New York, London, 1999.
7. [2c] M. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Nature 2002, 420, 759-760.
8. [3a] H. Stobbe, Ber. Dtsch. Chem. Ges. 1904, 37, 2232-2236.
9. [3b] H. G. Heller, T. J. Hart, J. Chem. Soc., Perkin Trans. 1 1972, 1321-1324.
10. [4a] M. Irie, Chem. Rev. 2000, 100, 1685-1716.
11. [4b] M. Irie, K. Uchida, Bull. Chem. Soc. Jpn. 1998, 71, 985-996.
12. [4c] L. N. Lucas, J. van Esch, R. M. Kellogg, B. L. Feringa, Chem. Commun. 1998, 2313-2314.
13. [4d] J. J. D. de Jong, L. N. Lucas, R. Hania, A. Pugzlys, R. M. Kellogg, B. L. Feringa, K. Duppen, J. H. van Esch, Eur. J. Org. Chem. 2003, 1887-1893.
14. F. Buchholtz, A. Zelichenok, V. Krongauz, Macromolecules 1993, 26, 906-910.
15. J. H. Simons, Fluorine Chemistry, Academic Press, New York, 1954.
16. [7a] O. Ruff, O. Z. Bretschneider, Z. Anorg. Allg. Chem. 1933, 210, 173-183.
17. [7b] J. H. Simons, R. L. Bond, R. E. McArthur, J. Am. Chem. Soc. 1940, 62, 3477-3480.
18. [8a] A. V. Grosse, G. H. Cady, Ind. Eng. Chem. 1947, 39, 367-374.
19. [8b] R. Y. Tompson, P. Tarrant, L. A. Bigelow, J. Am. Chem. Soc. 1946, 68, 2187-2192.
20. O. Ruff, R. Z. Keim, Z. Anorg. Allg. Chem. 1930, 192, 249-256.
21. [10a] J. H. Simons, L. P. Block, J. Am. Chem. Soc. 1939, 61, 2962-2966.
22. [10b] J. H. Simons, L. P. Block, J. Am. Chem. Soc. 1937, 59, 1407-1408.
23. [11a] D. E. Bergstom, D. J. Swartling, Fluorine-Containing Molecules (Ed.: J. F. Liebman), VCH, New York, 1988, p. 259-308.
24. [11b] R. Filler, Organofluorine Compounds in Medicinal Chemistry and Biochemical Applications, Elsevier, Amsterdam, 1993.
25. L. N. Lucas, J. V. Esch, R. M. Kellog, B. L. Feringa, Tetrahedron Lett. 1999, 40, 1775-1778.
26. [13a] D. Nees, M. A. Koschade, T. Wolff, P. Baglioni, L. Dei, Prog. Colloid Polym. Sci. 1996, 101, 75-85.
27. [13b] T. Saika, M. Irie, T. Shimidzu, J. Chem. Soc., Chem. Commun. 1994, 2123-2124.
28. T. Yamada, S. Kobatake, M. Irie, Bull. Chem. Soc. Jpn. 2002, 75, 167-173.
29. S. Kobatake, T. Yamada, K. Uchida, N. Kato, M. Irie, J. Am. Chem. Soc. 1999, 121, 2380-2386.
30. K. Higashiguchi, K. Matsuda, T. Yamada, T. Kawai, M. Irie, Chem. Lett. 2000, 1358-1359.
31. Y. Sakamoto, S. Komatsu, T. Suzuki, J. Am. Chem. Soc. 2001, 123, 4643-4644.
32. [18a] M. Irie, O. Miyatake, K. Uchida, T. Eriguchi, J. Am. Chem. Soc. 1994, 116, 9894-9900.
33. [18b] M. Takeshita, N. Kato, S. Kawauchi, T. Imase, J. Watanabe, M. Irie, J. Org. Chem. 1998, 63, 9306-9313.
34. K. Morimitsu, S. Kobatake, S. Nakamura, M. Irie, Chem. Lett. 2003, 32, 858-859.
35. [20a] S. Kobatake, K. Uchida, E. Tsuchida, M. Irie, Chem. Commun. 2002, 23, 2804-2805.
36. [20b] K. Higashiguchi, K. Matsuda, M. Matsuo, T. Yamada, M. Irie, J. Photochem. Photobiol. A: Chem. 2002, 152, 141-146.
37. S. Nakamura, M. Irie, J. Org. Chem. 1988, 53, 6136-6138.
38. K. Shibata, K. Muto, S. Kobatake, M. Irie, J. Phys. Chem. A 2002, 106, 209-214.
39. It has been reported that the calculation using 6-31G* has a similar accuracy to the calculation using 6-31G in ref.[21]
40. D. Guillaumont, S. Nakamura, Dyes Pigm. 2000, 46, 85-92.
41. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, 1998.
42. The calculation was performed with HF/STO-3G to obtain the LCAO coefficient of the p- orbitals. The model was optimized by B3LYP/6-31G calculations.
43. M. Irie, M. Mohri, J. Org. Chem. 1988, 53, 803-808.
44. K. Uchida, M. Irie, Chem. Lett. 1995, 969-970.
45. K. Uchida, E. Tsuchida, Y. Aoi, S. Nakamura, M. Irie, Chem. Lett. 1999, 63-64.
46. SAINTPLUS Software Package, Version 6, Bruker AXS, Madison, WI, 2001.
47. SHELXTL Software Package, Version 5, Bruker AXS, Madison, WI, 2001.