Oligothiophene-linked bisnaphthopyrans: Sequential and temperature- dependent photochromism

Chemistry - A European Journal

Volumn 13, Issue 9, 2007, Pages 2671-2685

  Zhao, Weili ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Dyes pigments; Heterocycles; Oligothiphene; Photochromism; Sensors

Indexed keywords

PHOTOCHROMISM; REACTION KINETICS; SENSORS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

DYES/PIGMENTS; HETEROCYCLES; OLIGOTHIPHENE;

OLIGOMERS;

EID: 34250771201     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600958     Document Type: Article

References (75)

1. J. C. Crano, R. Guglielmetti, Organic Photochromic and Thermochromic Compounds, Plenum Press, New York, 1999.
2. a) H. Dürr, H. Bouas-Laurent, Photochromism: Molecules and Systems, Elsevier, Amsterdam, 2003;
3. b) I. Willner, Acc. Chem. Res. 1997, 30, 347-356;
4. c) B. L. Feringa, Molecular Switches, Wiley-VCH, Weinheim, 2001.
5. For diarylethene, see: a) A. Peters, N. R. Branda, Adv. Mater. Opt. Electron. 2000, 10, 245-249;
6. b) K. Yagi, M. Irie, Chem. Lett. 2003, 32, 848-849;
7. c) K. Higashiguchi, K. Matsuda, M. Matsuo, T. Yamada, M. Irie, J. Photochem. Photobiol. A 2002, 152, 141-146;
8. d) A. Osuka, D. Fujikane, H. Shinmor, S. Kobatake, M. Irie, J. Org. Chem. 2001, 66, 3913-3923;
9. e) T. Kaieda, S. Kobatake, H. Miyasaka, M. Murakami, N. Iwai, Y. Nagata, A. Itaya, M. Irie, J. Am. Chem. Soc. 2002, 124, 2015-2024;
10. f) T. Kawai, T. Sasaki, M. Irie, Chem. Commun. 2001, 711-712;
11. g) K. Higashiguchi, K. Matsuda, M. Irie, Angew. Chem. 2003, 115, 3661-3664;
12. Angew. Chem. Int. Ed. 2003, 42, 3537-3540;
13. h) S. Kobatake, M. Irie, Tetrahedron 2003, 59, 8359-8364;
14. i) K. Matsuda, M. Irie, J. Am. Chem. Soc. 2001, 125, 9896-9897;
15. j) B. Chen, M. Wang, Q. Luo, H. Tian, Synth. Met. 2003, 137, 985-987;
16. k) Q. Luo, B. Chen, M. Wang, H. Tian, Adv. Funct Mater. 2003, 13, 233-239;
17. l) K. Higashiguchi, K. Matsuda, N. Tanifuji, M. Irie, J. Am. Chem. Soc. 2005, 127, 8922-8923.
18. For benzodihydropyrene, see: a) R. H. Mitchell, S. Bandyopadhyay, Org. Lett. 2004, 6, 1729-1732;
19. b) R.H. Mitchell, T. R. Ward, Y. Chen, Y. Wang, S. A. Weerawarna, P. W. Dibble, M. J. Marsellam, A. Almutair, Z. Wang, J. Am. Chem. Soc. 2003, 125, 2974-2988;
20. c) R. H. Mitchell, T. R. Ward, Y. Wang, P. W. Dibble, J. Am. Chem. Soc. 1999, 121, 2601-2602.
21. For spiropyrans, see: a) S. R. Keum, H.H. Lee, M. Seok, C.M. Yoon, Bull. Korean Chem. Soc. 1994, 15, 275-277;
22. b) S. R. Keum, H. H. Lee, M. K. Seok, Dyes Pigm. 1994, 25, 21-29;
23. c) S. R. Keum, S. S. Lee, B. H. Min, P. M. Kazmaier, E. Buncel, Dyes Pigm. 1996, 30, 225-234;
24. d) S. R. Keum, S.S. Lim, B. H. Min, Bull. Korean Chem. Soc. 1995, 16, 1007-1009;
25. e) S. R. Keum, Y. K. Choi, S. H. Kim, C.M. Yoon, Dyes Pigm. 1999, 41, 41-47;
26. f) Y.J. Cho, K. Y. Rho, S. H. Kim, S. R. Keum, C. M. Yoon, Dyes Pigm. 1999, 44, 19-25;
27. g) J. Filley, M. A. Ibrahim, M. R. Nimlos, A. S. Watt, D.M. Blake, J. Photochem. Photobiol. A 1998, 117, 193-198;
28. h) A. N. Flerova, N. P. Prokhoda, N. P. Yudina, E. L. Zaitseva, V. A. Krongauz, Chem. Heterocycl. Compd. 1973, 9, 1476-1482;
29. i) Ya. N. Malkin, V. A. Kuz'min, G. G. Dyadyusha, A. N. Boguslavskaya, F. A. Mikhailenko, Russ. Chem. Bull 1976, 25, 536-540;
30. j) F. Ribes, R. Guglielmetti, J. Metzger, Bull. Soc. Chim. Fr. 1972, 143-147;
31. k) Y. Strokach, M. Alfimov, V. Barachevsky, V. Arsenov, A. Gorelik, Mol. Cryst. Liq. Cryst. 1997, 295, 97-103;
32. l) A limited number of other bisspiropyrans have also been reported, however their photochromic properties were not addressed in detail, see for example : B. C. Bertelson, Photochromism (Ed.: G. H. Brown), Wiley-Interscience, New York, 1971, pp. 733-840.
33. For spirooxazines, see: a) T. J. Kang, S. H. Chang, D. J. Kim, Mol. Cryst. Liq. Cryst. 1996, 278, 181-188;
34. b) M. Melzig, H. Zinner, Eur. Patent EP 686685 A2, 1995;
35. c) H. Dürr, Y. Ma, German Patent DE 4444244, 1994.
36. For dihydroindolizines, see: a) M. Holderbaum, H. Dürr, E. Hadjoudis, J. Photochem. Photobiol. A 1991, 58, 37-50;
37. b) H. Bleisinger, P. Scheidhauer, H. Dürr, V. Wintgens, P. Valat, J. Kossanyi, J. Org. Chem. 1998, 63, 990-1000;
38. c) C. Weber, H. Dürr, R. Bonneau, Synthesis 1999, 1005-1012.
39. For diarylnaphthopyrans, see: a) A. Samat, V. Lokshin, K. Chamontin, D. Levi, G. Pepe, R. Guglielmetti, Tetrahedron 2001, 57, 7349-7359;
40. b) D. Coen, C. Moustrou, M. Frigoli, M. Julliard, A. Samat, R. Guglielmetti, J. Photochem. Photobiol. A 2001, 139, 1-4;
41. c) F. Ortica, D. Levi, P. Brun, R. Guglielmetti, U. Mazzucato, G. Facaro, J. Photochem. Photobiol. A 2001, 139, 133-141;
42. d) F. Ortica, D. Levi, P. Brun, R. Guglielmetti, U. Mazzucato, G. Favaro, J. Photochem. Photobiol. A 2001, 138, 123-128;
43. e) M. Frigoli, C. Moustrou, A. Samat, R. Guglielmetti, Helv. Chim. Acta 2000, 83, 3043-3052;
44. f) D. B. Knowles, B. Van Gemert, US Patent US 5464567, 1995;
45. g) G. Facaro, D. Levi, F. Ortica, A. Samat, R. Guglielmetti, J. Photochem. Photobiol. A 2002, 149, 91-100;
46. h) C. D. Gabbutt, T. Helbrich, J. D. Hepworth, B. M. Heron, M. B. Hursthouse, S. M. Partington, D. A. Thomas, Dyes Pigm. 2002, 54, 79-93;
47. i) K. Tanaka, H. Aoki, H. Hosomi, S. Ohba, Org. Lett. 2000, 2, 2133-2134;
48. j) A. E. Navarro, F. Moggia, C. Moustrou, A. Heynderickx, F. Pages, P. Leriche, H. Brisset, Tetrahedron 2005, 67, 423-428.
49. W. Zhao, E. M. Carreira, J. Am. Chem. Soc. 2002, 124, 1582-1583.
50. a) A. Yassar, N. R. Galy, M. Frigoli, C. Moustrou, A. Samat, R. Guglielmetti, A. Jaafari, Synth. Met. 2001, 124, 23-27;
51. b) A. Yassar, H. Jaafari, N. R. Galy, M. Frigoli, C. Moustrou, A. Samat, R. Guglielmetti, Eur. Phys. J. Appl. Phys. 2002, 5, 3-8.
52. N. Rebiere, C. Moustrou, M. Meyer, A. Samat, R. Guglielmetti, J. C. Micheau, J. Aubard, J. Phys. Org. Chem. 2000, 13, 523-530.
53. D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636-3638.
54. B. Von Gemert, Benzo and Naphthopyrans (Chromenes), in Organic Photochromic and Thermochromic Compounds, Vol. 1 (Eds.: J. C. Crano, R. Guglielmetti), Plenum Press. New York, 1999.
55. W. Zhao, E. M. Carreira, Org. Lett. 2003, 5, 4153-4154.
56. P. J. Coelho, M. A. Salvador, M. M. Oliveira, L. M. Carvalho, Tetrahedron 2004, 60, 2593-2599.
57. C. Moustrou, N. Rebiere, A. Samat, R. Guglielmetti, A. E. Yassar, R. Dubest, J. Aubard, Helv. Chim. Acta, 1998, 81, 1293-1302.
58. Lithium acetylide diamine complex (1.5 equiv) was used instead of sodium acetylide/acetylene gas.
59. a) M. Frioli, V. Pimienta, C. Moustrou, A. Samat, R. Guglielmetti, J. Aubard, F. Maurel, J. C. Micheau, Photochem. Photobiol. Sci. 2003, 2, 888-892;
60. b) S. Delbaere, J. C. Micheau, G. Vermeersch, J. Org. Chem. 2003, 68, 8968-8973.
61. R. Guglielmetti, Photochromism: Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam, 1990, p. 333.
62. a) G. Ottavi, G. Favaro, V. Malatesta, J. Photochem. Photobiol. A 1998, 115, 123-128;
63. b) G. Ottavi, F. Ortica, G. Favaro, Int. J. Chem. Kinet. 1999, 31, 303-313;
64. c) H. Görner, A. K. Chibisov, J. Photochem. Photobiol. A 2002, 149, 83-89.
65. R. S. Becker, A. P. Pelliccioli, A. Romani, G. Favaro. J. Am. Chem. Soc. 1999, 121, 2104-2109.
66. S. Delbaere, B. Buccioni-Houze, C. Bochu, Y. Teral, M. Campredon. G. Vermeersch, J. Chem. Soc. Perkin Trans. 2 1998, 1153-1157.
67. S. L. Murov, L. Carmichael, G. L. Hug, Handbook of Photochemistry, Marcel Dekker, New York, Basel, 1993, pp. 298-305.
68. J. V. Morris, M. A. Mahaney, J. R. Huber, J. Phys. Chem. 1976, 80, 969-974.
69. V. Malatesta, Photodegradation of Organic Photochromes, in: Organic Photochromic and Thermochromic Compounds, Vol. 2 (Eds.: J. C. Crano, R. Guglielmetti), Plenum Press, New York, 1999.
70. It is difficult to evaluate the stability of metastable open forms of pyrans in accurate manner, however, comparison of the absorbance at absorption maxima of open-open and closed-open forms permits such a conclusion. In the fatigue-resistance study of the closely-related spiropyrans, it is generally accepted that the open form (merocyanine) is more fatigue-prone than spiropyran itself, see the ref. [25].
71. R. Wu, J. S. Schumm, D. L. Pearson, J. M. Tour, J. Org. Chem. 1996, 61, 6906-6921.
72. E. J. Stoner, D. A. Cothron, M. K. Balmer, B. A. Roden, Tetrahedron 1995, 51, 11043-11062.
73. K. O. Jeon, J. H. Jun, J. S. Yu, C. K. Lee, J. Heterocycl. Chem. 2003, 40, 763-771.
74. O. Rahman, T. Kihlberg, B. Langström, Eur. J. Org. Chem. 2004, 3, 474-478.
75. D. R. Arnold, R. J. Birtwell, J. Am. Chem. Soc. 1973, 95, 4599-4606.