Multi-mode switching based on dihydroazulene/vinylheptafulvene photochromism: Synergism of photochromism and redox switching in heteroaryl-functionalized systems

Chemistry - A European Journal

Volumn 2, Issue 9, 1996, Pages 1150-1158

  Spreitzer, Hubert ^a,b   Daub, Jörg ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b SANOFI   (France)

Author keywords

Cyclic voltammetry; Electrochromes; Heterocycles; Optical memory; Photochromes

Indexed keywords

ELECTROCHROMES; HETEROCYCLES; HIGH SENSITIVITY; ONE-ELECTRON TRANSFER; OXIDATION AND REDUCTION; OXIDATIVE DIMERIZATION; PHOTOCHROMES; REDOX SWITCHING;

CYCLIC VOLTAMMETRY; ELECTRONIC PROPERTIES; FREE RADICAL REACTIONS; FUNCTIONAL GROUPS; OPTICAL DATA STORAGE; SPECTROELECTROCHEMISTRY;

PHOTOCHROMISM;

EID: 0000886127     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020918     Document Type: Article

References (64)

1. Preceeding publication: J. Daub, M. Beck, A. Knorr, H. Spreitzer, Pure Appl. Chem., 1996, 68, 1399.
2. a) Molecular Electronics - Science and Technology, AIP Conference Proceedings 262 (Ed. A. Aviram), American Institute of Physics, New York, 1992;
3. b) A. Aviram, J. Am. Chem. Soc. 1988, 110, 5687-5692;
4. c) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267;
5. d) J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1990, 29, 1304;
6. e) Photochemistry and Polymer Systems (Eds.: J. M. Kelly, C. B. McArdle, M. J. de F. Maunder), Royal Society of Chemistry, Cambridge, 1993.
7. a) J. Daub, J. Salbeck, T. Knöchel, C. Fischer, H. Kunkely, K. M. Rapp, Angew. Chem. 1989, 101, 1541;
8. Angew. Chem. Int. Ed. Engl. 1989, 28, 1494;
9. b) J. Daub, C. Fischer, J. Salbeck. K. Ulrich, Adv. Mater. 1990, 2, 366;
10. c) J. Achatz, C. Fischer, J. Salbeck, J. Daub, J. Chem. Soc. Chem. Commun. 1991, 504;
11. d) J. Daub, S. Gierisch, J. Salbeck, Tetrahedron Lett. 1990, 31, 3113;
12. e) J. Daub, C. Fischer, S. Gierisch, J. Sixt, Mol. Cryst. Liq. Cryst. 1992, 217, 177;
13. f) P. A. Bross, A. Mirlach, J. Salbeck, J. Daub, DECHEMA Monogr. 1990, 121, 375-382.
14. a) T. Iyoda, T. Saika, K. Honda, T. Shimidzu, Tetrahedron Lett. 1989, 30, 5429;
15. b) Z. F. Liu, K. Hashimoto, A. Fujishima, Nature 1990, 347, 658-660;
16. c) A. A. Solov'ev, E. Y. Katz, V. A. Shuvalov, Y. E. Erokhin, Bioelectrochem. Bioenerg. 1991, 26, 29-41;
17. d) Z. F. Liu, B. H. Loo, K. Hashimoto, A. Fujishima, J. Etectroanal. Chem. 1991, 297, 133-144;
18. e) T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Perkin Trans. 2 1993, 1181;
19. f) V. Goulle, A. Harriman, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1034-1036;
20. g) T. Saika, M. Irie, T. Shimidzu, ibid. 1994, 2123 2124;
21. h) M. Lion-Dagan, E. Katz, I. Willner, J. Am. Chem. Soc. 1994, 116, 7913-7914;
22. i) M. Nakagawa, M. Rikukawa, M. Watanabe, K. Sanui, N. Ogata, Chem. Lett. 1994, 1785-1788;
23. j) S. H. Kawai, S. L. Gilat, R. Ponsinet, J.-M. Lehn, Chem. Eur. J. 1995, 1, 285-293;
24. k) S. L. Gilat, S. H. Kawai, J.-M. Lehn, ibid. 1995, 1, 275-284.
25. a) M. Campredon, G. Giusti, R. Guglielmetti. A. Samat, G. Gronchi, A. Alberti, M. Benaglia, J. Chem. Soc. Perkin Trans. 2 1993, 2089-2094;
26. b) J. F. Zhi, R. Baba, K. Hashimoto, A. Fujishima, Ber. Bunsenges. Phys. Chem. 1995, 99, 32-39;
27. c) A. K. Newell, J. H. P. Utley, J. Chem. Soc. Chem. Commun. 1992, 800.
28. H. Spreitzer, Thesis, University of Regensburg, 1995.
29. J. Salbeck, V. M. Komissarov, V. I. Minkin, J. Daub, Angew. Chem. 1992, 104, 1498;
30. Angew. Chem. Int. Ed. Engl. 1992, 31, 1498.
31. a) Phenothiazines and 1,4-Benzothiazines - Chemical and Biochemical Aspects (Ed.: R. R. Gupta), Elsevier, Amsterdam, 1988;
32. b) Comprehensive Heterocyclic Chemistry (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984.
33. a) C. Bodea, I. Silberg, Adv. Heterocycl. Chem. 1968, 9, 321-460;
34. b) Methoden Org. Chem. (Houben-Weyl), Vol. E9 (Ed.: E. Schaumann), Thieme, Stuttgart, 1995/96.
35. a) J. Daub, T. Knöchel, A. Mannschreck, Angew. Chem. 1984, 96, 980;
36. Angew. Chem. Int. Ed. Engl. 1984, 23, 960;
37. b) J. Daub, S. Gierisch, U. Klement, T. Knöchel, G. Maas, U. Seitz, Chem. Ber. 1986, 119, 2631;
38. c) S. Gierisch, J. Daub, ibid. 1989, 122, 69-75;
39. d) S. Gierisch, W. Bauer, T. Burgemeister, J. Daub, ibid. 1989, 122, 2341.
40. A. Hasenhündl, K. M. Rapp, J. Daub, Chem. Lett. 1979, 597.
41. S. Gierisch, Thesis, Regensburg University, 1989.
42. C. Fischer, J. Daub, Chem. Ber. 1993, 126, 1631.
43. A comparable hypochromic shift is also observed by the compounds with ortho-nitrophenyl at C-2: H. Görner, C. Fischer, J. Daub, J. Photochem. Photobiol. A: Chem. 1995, 85, 217-224.
44. We anticipate that because of the push/pull stabilization of the VHF forms, the DHA(a-e)/VHF(a-e) interconversion leads to an off/on switching of second-order hyperpolarizability (ref. [3e]). Qualitatively, the significant positive solvatochromism is strong indication of an exalted second-order hyperpolarizability in VHF (ref. [18a]).
45. S. Gierisch, J. Daub, Chem. Ber. 1989, 122, 69-75.
46. H. Görner, C. Fischer, S. Gierisch, J. Daub, J. Phys. Chem. 1993, 97, 4110.
47. a) J. Bindl, P. Seitz, U. Seitz, E. Salbeck, J. Salbeck, J. Daub, Chem. Ber. 1987, 120, 1747-1756;
48. b) M. Baumgarten, K. Müllen, Top. Curr. Chem. 1994, 169, 1-103.
49. Hubert Hirschlag, Diploma Thesis, Regensburg University, 1995.
50. Recommended Methods for Purification of Solvents and Tests for Impurities (Ed.: J. F. Coetze), Pergamon, Oxford, 1983.
51. a) J. Salbeck, I. Aurbach, J. Daub, DECHEMA Monogr. 1988, 112, 177;
52. b) J. Salbeck, J. Electroanal. Chem. 1992, 340, 169;
53. c) J. Salbeck, Anal. Chem. 1993, 65, 2169.
54. H. Spreitzer, M. Scholz, G. Gescheidt, J. Daub, Liebigs Ann., in press.
55. See: a) V. D. Pokhodenko, V. G. Koshechko, A. N. Inozemtsev, J. Chem. Soc. Chem. Commun. 1985, 72;
56. b) K. Shindo, S. Ishikawa, T. Nozoe, Bull. Chem. Soc. Jpn. 1989, 62, 1158.
57. H. Gilman, J. J. Dietrich, J. Am. Chem. Soc. 1957, 79, 6178.
58. cf. a) H. Gilman, S. H. Eidt, J. Am. Chem. Soc. 1956, 78, 2633;
59. b) B. D. Palmer, G. W. Rewcastle, G. J. Atwell, B. C. Baguley, W. A. Denny, J. Med. Chem. 1988, 31, 707;
60. c) B. D. Palmer, M. Boyd, W. A. Denny, J. Org. Chem. 1990, 55, 438.
61. H. H. Lee, W. A. Denny, J. Chem. Soc. Perkin Trans. 1, 1990, 1071.
62. a) T. Knöchel, Thesis, Regensburg University, 1985;
63. b) J. Daub, G. Hirmer, L. Jakob, G. Maas, W. Pickl, E. Pirzer, K. M. Rapp, Chem. Ber. 1985, 118, 1836-1856.
64. 6 (stored under argon) has to be used.