Thermally reversible photochromism of pyrazole derivatives

Chemistry Letters

Volumn 33, Issue 2, 2004, Pages 106-107

  Yokoyama, Yasushi ^a   Kurimoto, Yuko ^a   Saito, Yasuyo ^b   Katsurada, Manabu ^b   Okada, Itaru ^b   Osano, Yasuko T ^b   Sasaki, Chizuko ^b   Yokoyama, Yayoi ^c   Tukada, Hideyuki ^d   Adachi, Masafumi ^b   Nakamura, Shinichiro ^b   Murayama, Tetsuo ^b   Harazono, Toshie ^b   Kodaira, Tetsuya ^e  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

^b MITSUBISHI CHEMICAL CORPORATION   (Japan)

^c TOKYO KASEI GAKUIN UNIVERSITY   (Japan)

^d YOKOHAMA CITY UNIVERSITY   (Japan)

^e NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ETHYL 4 FORMYL 1,3 DIMETHYLPYRAZOLE 5 CARBOXYLATE; FURAN DERIVATIVE; HYDROGEN; METHYL GROUP; OXYGEN; PYRAZOLE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DISSOLUTION; LIGHT; LIGHT IRRADIANCE; LOW TEMPERATURE; PHOTOCHEMISTRY; REACTION ANALYSIS; ROOM TEMPERATURE; SOLID STATE; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; THERMAL ANALYSIS;

EID: 11144356539     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.106     Document Type: Article

References (16)

1. a) "Photochromism: Molecules and Systems," ed. by H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam (1990).
2. b) "Organic Photochromic and Thermochromic Compounds," ed. by J. C. Crano and R. Guglielmetti, Plenum Publishers, New York (1999).
3. a) M. Irie, S. Kobatake, and M. Horichi, Science, 291, 1769 (2001).
4. b) K. Tanaka and F. Toda, J. Chem. Soc., Perkin Trans. 1, 2000, 873.
5. E.g. a) V. A. Kumar and K. Venkatesan, J. Chem. Soc., Perkin Trans. 2, 1991, 829. b) T. K. Sakar, S. K. Ghosh, J. N. Moodthy, J.-M. Fang, S. K. Nandy, N. Sathyamurthy, and D. Chakraborty, Tetrahedron Lett., 41, 6909 (2000).
6. E.g. a) V. A. Kumar and K. Venkatesan, J. Chem. Soc., Perkin Trans. 2, 1991, 829. b) T. K. Sakar, S. K. Ghosh, J. N. Moodthy, J.-M. Fang, S. K. Nandy, N. Sathyamurthy, and D. Chakraborty, Tetrahedron Lett., 41, 6909 (2000).
7. The ester cognates of 1 (methyl and propyl) showed coloration. However, 2-propyl and butyl esters did not.
8. N. J. Turro, "Modern Molecular Photochrmistry," The Benjamin/Cummings Publishing Co., Inc., Menlo Park (1978), Chap. 10.
9. S. Maeda, I. Okada, and M. Katsurada, Jpn. Kokai Tokkyo Koho JP11 05972 [99 05972] (1999); Chem. Abstr., 130, 131620c (1999).
10. 3, TMS): 1.44 (3H, t, J/Hz = 7.09), 2.49 (3H, s), 4.14 (3H, s), 4.47 (2H, q, J/Hz = 7.25), 10.39 (1H, s).
11. ZINDO (INDO/S) calculations were done for AM1-optimized conformation of 1Q.
12. B. A. Johnson, A. Gamarnik, and M. A. Garcia-Garibay, J. Am. Chem. Soc., 100, 4697 (1996).
13. Although the colored species can be a singlet biradical, we also ruled it out from the energetic consideration. Details including other possible isomers of 1Q will be reported in due course.
14. Crystallographic data reported in this paper have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-221042. Copies of the data can be obtained free of charge via www.ccdc.cam.ac.uk/ conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk). Instruction for depositing the crystallographic data is available on the Web at http://www.ccdc.cam.ac.uk/ conts/depositing. html.
15. L. J. Bellamy, "The Infra-red Spectra of Complex Molecules," 3rd ed., Halsted Press, New York (1975), Part 1, Chap. 6, pp 107-128; Part 2, Chap. 8, pp 240-292.
16. L. J. Bellamy, "The Infra-red Spectra of Complex Molecules," 3rd ed., Halsted Press, New York (1975), Part 1, Chap. 6, pp 107-128; Part 2, Chap. 8, pp 240-292.