Spirooxazine to merooxazine interconversion in the presence and absence of zinc: Approach to a bistable photochemical switch

Journal of Physical Chemistry A

Volumn 114, Issue 44, 2010, Pages 11900-11909

  Tian, Zhiyuan ^a   Stairs, Robert A ^b   Wyer, Martin ^a   Mosey, Nicholas ^a   Dust, Julian M ^c   Kraft, Thomas M ^a   Buncel, Erwin ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b TRENT UNIVERSITY   (Canada)

^c MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78149312775     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp106501e     Document Type: Article

References (50)

1. Crano, J. C., Guglielmetti, R. J., Eds.; Organic Photochromic and Thermochromic Compounds; Topics in Applied Chemistry; Kluwer Academic/Plenum: New York, 1999; Vols. 1 and 2.
2. Dürr, H., Bouas-Laurent, H., Eds. Photochromism, Molecules and Systems in Studies in Organic Chemistry; Elsevier: Amsterdam, 1990; Vol. 40.
3. Hirschberg, Y. J. Am. Chem. Soc. 1956, 78, 2304-2312
4. Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000, 100, 1741-1754
5. Kawata, S.; Kawata, Y. Chem. Rev. 2000, 100, 1777-1788
6. Irie, M. Chem. Rev. 2000, 100, 1630
7. Wojtyk, J. T. C.; Kazmaier, P. M.; Buncel, E. J. Chem. Soc., Chem. Commun. 1998, 1703-1704
8. Wojtyk, J. T. C.; Wasey, A.; Kazmaier, P. M.; Hoz, S.; Buncel, E. J. Phys. Chem. A. 2000, 104, 9046-9055
9. Feringa, B. L.; Lager, W. F.; DeLange, B. Tetrahedron 1993, 49, 8267-8310
10. Parthenopoulos, D. A.; Rentzepis, P. M. Science 1989, 245, 843-845
11. Piyaket, R.; Cokgor, I.; McCormick, F. B.; Esener, S.; Dvornikov, A. S.; Rentzepis, P. M. Opt. Lett. 1996, 14, 1032-1034
12. Dvornikov, A. S.; Walker, E. P.; Rentzepis, P. M. J. Phys. Chem. A. 2009, 113, 13633-13644
13. Piantik, M.; Schulze, G.; Koch, M.; Franke, K. J.; Leyssner, F.; Kruger, A.; Navia, C.; Miguel, J.; Bernien, M.; Wolf, M.; Kuch, W.; Tegeder, P.; Pascual, J. I. J. Am. Chem. Soc. 2009, 131, 12729-12735
14. Muhlstein, L. A.; Sauer, J.; Bein, T. Adv. Funct. Mater. 2009, 920, 332-341
15. Rosario, R.; Gust, D.; Hayes, M.; Springer, J.; Garcia, A. A. Langmuir 2003, 19, 8801-8806
16. Suzuki, T.; Lin, F. T.; Priyadashy, S.; Weber, S. G. Chem. Commun. 1998, 24, 2685-2686
17. Xiao, N. N.; Chen, Y.; Lemieux, R.; Buncel, E.; Iftime, G.; Kazmaier, P. M. Mol. Cryst. Liq. Cryst. 2005, 431, 337-344
18. Wojtyk, J. T. C.; Wasey, A.; Xiao, N. N.; Kazmaier, P. M.; Hoz, S.; Yu, C.; Lemieux, R. P.; Buncel, E. J. Phys. Chem. A. 2007, 111, 2511-2516
19. Wojtyk, J. T. C.; Kazmaier, P. M.; Buncel, E. Chem. Mater. 2001, 13, 2547-2551
20. Keum, S. R.; Ku, B. S.; Shin, J. T.; Ko, J. J.; Buncel, E. Tetrahedron 2005, 61, 6720-6725
21. Keum, S. R.; Lee, M. J.; Swansburg, S.; Buncel, E.; Lemieux, R. P. Dyes Pigments 1998, 39, 383-388
22. Harbron, E. J.; Davis, C. M.; Campbell, J. K.; Allred, R. M.; Kovary, M. T.; Economou, N. J. J. Phys. Chem.. C 2009, 113, 13707-13714
23. Raboin, L.; Matheron, M.; Biteau, J.; Gacoin, T.; Boilot, J. P. J. Mater. Chem.. 2008, 18, 3242-3248
24. Wu, Y.; Sasaka, T.; Kazushi, K.; Seo, T.; Sakurai, K. J. Phys. Chem. B 2008, 112, 7530-7536
25. Yee, L. H.; Hanley, T.; Evans, R. A.; Davis, T. P.; Ball, G. E. J. Org. Chem. 2010, 75, 2851-2860
26. Swansburg, S.; Choi, Y. K.; Keum, S. R.; Buncel, E.; Lemieux, R. P. Liq. Cryst. 1998, 24, 341-346
27. Whelan, J.; Wojtyk, J. T. C.; Buncel, E. Chem. Mater. 2008, 20, 3797-3799
28. Lokshin, V.; Samat, A.; Metelitsa, A. V. Russ. Chem. Rev. 2002, 71, 893-916
29. Bertelson, R. C. Photochromism; Brown, G. H., Ed.; Wiley-Interscience: New York, 1971; Ch. 3.
30. Bohne, C.; Fang, M. G.; Li, Z. J.; Liang, Y. C.; Lusztyk, J.; Scaiano, J. C. J. Photchem. Photobiol. A: Chem. 1992, 66, 79-90
31. Nishikiori, H.; Tanaka, N.; Takagi, K.; Fujii, T. J. Photochem. Photobiol. A: Chem. 2007, 189, 46-54
32. Nishikiori, H.; Tanaka, N.; Takagi, K.; Fujii, T. J. Photochem. Photobiol. A: Chem. 2006, 183, 53-58
33. Lokshin, V.; Samat, A.; Metelitsa, A. V. Russ. Chem.. Rev. 2002, 71, 893-916
34. Maurel, F.; Aubard, J.; Rajzmann, M.; Gugliemetti, R.; Samat, A. J. Chem. Soc. 2002, 1307-1315
35. Berthet, J.; Delbaere, S.; Carvalho, L. M.; Vermeersch, G.; Coelho, P. J. Tetrahedron Lett. 2006, 47, 4903-4905
36. Delbaere, S.; Bochu, C.; Azaroual, N.; Buntinx, G.; Vermeersch, G. J. Chem.. Soc. Perkin Trans 2 1997, 1499-1501
37. Berthet, J.; Delbaere, S.; Lokshin, V.; Bochu, C.; Samat, A.; Guglielmetti, R.; Vermeersch, G. Photochem. Photobiol. Sci. 2002, 1, 333-339
38. Preigh, M. J.; Lin, F. T.; Ismail, K. Z.; Weber, S. G. Chem. Commun. 1995, 2091-2092
39. Johnson, D. E.; Applied Multivariate Methods for Data Analysis; Duxbury Press: Pacific Grove, CA, U.S.A.; 1998; Ch. 5.
40. Chu, N. Y. C. Can. J. Chem. 1983, 61, 300-305
41. Grzybkowski, W.; Pilarczyk, M. Electrochim. Acta 1990, 35, 351-355
42. Diamond, A.; Fanelli, A.; Petrucci, S. Inorg. Chem. 1973, 12, 611-619
43. Kim, S. H.; Wang, S.; Ahn, C. H.; Choi, M. S. Fibers Polymers 2007, 8, 447-449
44. Jeliazkova, B. G.; Minkovska, S.; Deligeorgiev, T. J. Photochem. Photobiol. A. 2005, 171, 153-160
45. Bunnett, J. F. In Techniques in Organic Chemistry. Rates and Mechanisms of Reactions. Part 1; 2 nd ed.; Weissberger, A., Ed.; Interscience: New York, 1961, pp 199 ? 202.
46. Keum, R.; Hur, M. S.; Kazmaier, P. M.; Buncel, E. Can. J. Chem. 1991, 69, 1940-1947
47. Buncel, E.; Stairs, R.; Dust, J.; Tian, Z.; Wyer, M.; Kraft, T.; Mosey, N. Poster P7 presented at 10th Annual Centre for Research in Molecular Modelling Symposium, Concordia University, Montreal, Canada, 2010.
48. Hatchard, H.; Parker, C. A. Proc. Royal Soc. London A 1956, 235, 518-529
49. Montalti, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry, 3rd ed.; Taylor and Francis: Boca Raton, LA, U.S.A., 2006; pp 601 ? 604.
50. Zaichenko, N. L.; Shiyonok, A. I.; Kol'tsova, L. S.; Marevtsev, V. S. Mol. Cryst. Liq. Cryst. 2005, 431, 383-389