Large geometrical structure changes of photochromic diarylethenes upon photoirradiation

Tetrahedron Letters

Volumn 45, Issue 6, 2004, Pages 1155-1158

  Morimitsu, Kentaro ^a   Kobatake, Seiya ^a   Irie, Masahiro ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Diarylethene; Photochromism; Substituent effect

Indexed keywords

CARBON; ETHYLENE DERIVATIVE;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; GEOMETRY; IRRADIATION; ISOMERIZATION; QUANTUM CHEMISTRY; SYNTHESIS;

EID: 0742287096     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.005     Document Type: Article

References (23)

1. Dürr H., Bouas-Laurent H. Photochromism: Molecules and Systems. 1990;Elsevier, Amsterdam.
2. Irie M., Uchida K. Bull. Chem. Soc. Jpn. 71:1998;985-996.
3. Irie M. Chem. Rev. 100:2000;1685-1716.
4. Irie M., Kobatake S., Horichi M. Science. 291:2001;1769-1772.
5. Irie M., Fukaminato T., Sasaki T., Tamai N., Kawai T. Nature. 420:2002;759-760.
6. 2: C, 71.09; H, 3.20. Found: C, 71.07; H, 3.16.
7. Pereira R., Iglesias B., de Lera A.R. Tetrahedron. 57:2001;7871-7881.
8. 2: C, 69.37; H, 2.83. Found: C, 69.03; H, 2.74.
9. 2: C, 67.29; H, 4.20. Found: C, 67.36; H, 4.24.
10. 2: C, 65.02; H, 3.87. Found: C, 65.03; H, 3.85.
11. 1b was isolated by HPLC (silica gel; hexane/ethyl acetate=90/10 as the eluent). 1a and 1b were eluted at 20 and 32 min, respectively.
12. Irie M., Lifka T., Kobatake S., Kato N. J. Am. Chem. Soc. 122:2000;4871-4876.
13. Shibata K., Kobatake S., Irie M. Chem. Lett. 2001;618-619.
14. Morimitsu K., Shibata K., Kobatake S., Irie M. J. Org. Chem. 67:2002;4574-4578.
15. Morimitsu K., Shibata K., Kobatake S., Irie M. Chem. Lett. 2002;572-573.
16. Morimitsu K., Kobatake S., Nakamura S., Irie M. Chem. Lett. 32:2003;858-859.
17. 2b was isolated by HPLC (silica gel; hexane/ethyl acetate=99/1 as the eluent). 2a and 2b were eluted at 29 and 41 min, respectively.
18. 4b was isolated by HPLC (silica gel; hexane/ethyl acetate=90/10 as the eluent). 4a and 4b were eluted at 26 and 35 min, respectively.
19. 5b was isolated by HPLC (silica gel; hexane/ethyl acetate=99/1 as the eluent). 5a and 5b were eluted at 27 and 30 min, respectively.
20. Uchida K., Tsuchida E., Aoi Y., Nakamura S., Irie M. Chem. Lett. 1999;63-64.
21. 3, goodness of fit=0.964, R1[I>2σ(I)]=0.0527 , wR2(all data)=0.1339 . Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 219008.
22. 3, goodness of fit=1.020, R1[I>2σ(I)]=0.0623 , wR2(all data)=0.1690 . Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 219009.
23. Kobatake S., Uchida K., Tsuchida E., Irie M. Chem. Commun. 2002;2804-2805.