Photochromic properties of thermally irreversible 6-aryloxy-5,12-naphthacenequinones

Chemistry Letters

Volumn , Issue 5, 1996, Pages 355-356

  Yokoyama, Yasushi ^a   Fukui, Shin Ya ^a   Yokoyama, Yayoi ^b  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

^b TOKYO KASEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030500058     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.355     Document Type: Article

References (11)

1. Yu. E. Gerasimenko and N. T. Poteleshenko, Zh. Vses. Khim. Ova., 16, 105 (1971).
2. Yu. E. Gerasimenko and N. T. Poteleshenko, Zh. Org. Khim., 7, 2413 (1971).
3. With our preliminary experiments, 3-para was stable for more than 10 h in toluene at 78°C. To the contrary, 3-ana decomposed gradually and irreversibly (ca. 0.5 mol% per h), but did not form 3-para under these conditions. Addition of water accelerated the decomposition.
4. J. Malkin, A. Zelichenok, V. Krongauz, A. S. Dvornikov, and P. M. Rentzepis, J. Am. Chem. Soc., 116, 1101 (1994).
5. A review has been published: A. V. El'tsov, A. I. Ponyaev, E. R. Zakhs, D. Klemm, and E. Klemm, "Photochromic Peri-aryloxy-p-quinones," in "Organic Photochromes," ed by A. V. El'tsov, translated from Russian by Y. E. Sviridov, and the translation ed by J. Whittall, Consultants Bureau, New York (1990), part of Chap. 4, pp. 210-217.
6. Yu. E. Gerasimenko, A. A. Parshutkin, N. T. Poteleshenko, V. P. Poteleshenko, and V. V. Romanov, Zh. Prikl. Spektrosk., 30, 954 (1979).
7. Z. Fang, S. Wang, Z. Yang, B. Chen., F. Li, J. Wang, Z. Jiang, and T. Fang, J. Photochem. Photobiol. A: Chem., 88, 23 (1995).
8. F. Buchholtz, A. Zelichenok, and V. Krongauz, Macromolecules, 26, 906 (1993).
9. Analyses of photochromic reactions were done with the same procedures as for fulgides, which were reported in our recent paper: Y. Yokoyama, T. Inoue, M. Yokoyama, T. Goto, T. Iwai, N. Kera, I. Hitomi, and Y. Kurita, Bull. Chem. Soc. Jpn., 67, 3297 (1994). It is an important fact that the para-and ana-forms of 1-5 were stable and did not isomerize to each other in the silica-gel HPLC columns.
10. ZINDO calculations were done on a CAChe system.
11. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985). AMI calculations were done on a CAChe system for the ana-form of each compound to give the most stable conformation, for which vibrational analysis ascertained its appropriateness.