Optical ON/OFF switching of intramolecular photoinduced charge separation in a donor-bridge-acceptor system containing dithienylethene

Journal of the American Chemical Society

Volumn 122, Issue 13, 2000, Pages 3037-3046

  Endtner, Jochen M ^a   Effenberger, Franz ^a   Hartschuh, Achim ^a   Port, Helmut ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE; ETHYLENE; PYRIDINIUM DERIVATIVE; THIOPHENE;

ARTICLE; CONJUGATION; CYCLIC POTENTIOMETRY; CYCLIZATION; ELECTRON TRANSPORT; ISOMERISM; OPTICS; PHOTOACTIVATION; SURFACE CHARGE; THERMODYNAMICS; ULTRAVIOLET SPECTROSCOPY;

EID: 0034607378     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9938736     Document Type: Article

References (70)

1. (a) Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, 1995; Chapter 8, pp 89-138.
2. (b) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: New York, 1991; Chapter 12, pp 355-394.
3. (c) Ashwell, G. J. Molecular Electronics; Research Studies Press: Taunton, Somerset, 1992.
4. (a) Kurreck, H.; Huber, M. Angew. Chem. 1995, 107, 929-447; Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
5. (a) Kurreck, H.; Huber, M. Angew. Chem. 1995, 107, 929-447; Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
6. (b) Gust, D. Nature 1997, 386, 21-22 and references therein.
7. (a) Hartschuh, A.; Port, H.; Wolf, H. C.; Miehlich, B.; Endtner, J. M.; Vollmer, M. S.; Effenberger, F. J. Lumin. 1998, 76 and 77, 655-657.
8. (b) Hirsch, T.; Port, H.; Wolf, H. C.; Miehlich, B.; Effenberger, F. J. Phys. Chem. 1997, B101, 4525-4535.
9. (a) Vollmer, M. S.; Effenberger, F.; Stümpfig, T.; Hartschuh, A.; Port, H.; Wolf, H. C. J. Org. Chem. 1998, 63, 5080-5087.
10. (b) Vollmer, M. S.; Würthner, F.; Effenberger, F.; Emele, P.; Meyer, D. U.; Stümpfig, T.; Port, H.; Wolf, H. C. Chem. - Eur. J. 1998, 4, 260-269.
11. (c) Würthner, F.; Vollmer, M. S.; Effenberger, F.; Emele, P.; Meyer, D. U.; Port, H.; Wolf, H. C. J. Am. Chem. Soc. 1995, 117, 8090-8099.
12. (a) Walz, J.; Ulrich, K.; Port, H.; Wolf, H. C.; Wonner, J.; Effeberger, F. Chem. Phys. Lett. 1993, 213, 321-324.
13. (b) Port, H.; Hennrich, M.; Seibold, M.; Wolf, H. C. Proc. - Electrochem. Soc. 1998, 98-25 (Excitonic Processes in Condensed Matter), 61-70.
14. Tsuchiya, S. J. Am. Chem. Soc. 1999, 121, 48-53.
15. Gosztola, D.; Niemczyk, M. P.; Wasielewski, M. R. J. Am. Chem. Soc. 1998, 120, 5118-5119.
16. Lainé, P.; Marvaud, V.; Gourdon, A.; Launay, J.-P.; Argazzi, R.; Bignozzi, C.-A. Inorg. Chem. 1996, 35, 711-714.
17. Gilat, S. L.; Kawai, S. H.; Lehn, J.-M. Chem. - Eur. J. 1995, 1, 275-284.
18. Effenberger, F.; Niesert, C.-P. Synthesis 1992, 1137-1144.
19. Effenberger, F.; Miehlich, B.; Endtner, J. M.; Vollmer, M. S.; Münter, J. S. R.; Hartschuh, A.; Lehle, J.; Port, H.; Wolf, H. C. Publication in preparation.
20. (a) Irie, M.; Mohri, M. J. Org. Chem. 1988, 53, 803-808.
21. (b) Hanazawa, M.; Sumiya, R.; Horikawa, Y.; Irie, M. J. Chem. Soc., Chem. Commun. 1992, 206-207.
22. Irie, M.; Uchida, K. Bull. Chem. Soc. Jpn. 1998, 71, 985-996.
23. (a) Fernández-Acebes, A.; Lehn, J.-M. Adv. Mater. 1998, 10, 1519-1522.
24. (b) Tsivgoulis, G. M.; Lehn, J.-M. Adv. Mater. 1997, 9, 39-42.
25. (c) Kawai, S. H.; Gilat, S. L.; Ponsinet, R.; Lehn, J.-M. Chem. - Eur. J. 1995, 1, 285-293.
26. (d) Irie, M.; Eriguchi, T.; Takada, T.; Uchida, K. Tetrahedron 1997, 53, 12263-12271.
27. (e) Bens, A. T.; Frewert, D.; Kodatis, K.; Kryschi, C.; Martin, H.-D.; Trommsdorff, H. P. Eur. J. Org. Chem. 1998, 2333-2338.
28. Tsivgoulis, G. M.; Lehn, J.-M. Chem.-Eur. J. 1996, 2, 1399-1406.
29. Brandsma, L.; Verkruijsse, H. D. Preparative Polar Organometallic Chemistry 1; Springer: Berlin, 1987; p 124.
30. Endtner, J. Dissertation in preparation. Universität Stuttgart.
31. Davies, S. G.; Goodfellow, C. L. Synlett 1989, 59-62.
32. Lau, C. K.; Dufresne, C.; Bélanger, P. C.; Piétré, S.; Scheigetz, J. J. Org. Chem. 1986, 51, 3038-3043.
33. Tsivgoulis, G. M.; Lehn, J.-M. Adv. Mater. 1997, 9, 627-630.
34. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
35. (b) Martin, A. R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221-230.
36. (c) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513-519.
37. (d) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
38. (e) Zhang, H.; Kwong, F. Y.; Tian, Y.; Chan, K. S. J. Org. Chem. 1998, 63, 6886-6890.
39. (a) Vollmer, M. S. Dissertation, Universität Stuttgart, 1996.
40. (b) Spitzner, D. In Houben Weyl, Methoden der Organischen Chemie, 4th ed.; Kreher, R. P., Ed.; Thieme: Stuttgart, 1992; Vol. E7b, Part 2, pp 678-680 and references therein.
41. BIOSYM Insight II, Discover 95.0/3.00, CVFF Force field.
42. Saika, T.; Irie, M.; Shimidzu, T. J. Chem. Soc., Chem. Commun. 1994, 2123-2124.
43. (a) Knoll, K.; Schrock, R. R. J. Am. Chem. Soc. 1989, 111, 7989-8004.
44. (b) Brédas, J. L.; Silbey, R.; Boudreaux, D. S.; Chance, R. R. J. Am. Chem. Soc. 1983, 105, 6555-6559.
45. (c) Kiehl, A.; Eberhardt, A.; Adam, M.; Enkelmann, V.; Mullen, K. Angew. Chem. 1992, 104, 1623-1626; Angew. Chem., Int. Ed. Engl. 1992, 31, 1588-1591.
46. (c) Kiehl, A.; Eberhardt, A.; Adam, M.; Enkelmann, V.; Mullen, K. Angew. Chem. 1992, 104, 1623-1626; Angew. Chem., Int. Ed. Engl. 1992, 31, 1588-1591.
47. Irie, M.; Sakemura, K.; Okinaka, M.; Uchida, K. J. Org. Chem. 1995, 60, 8305-8309.
48. (a) Würthner, F. Dissertation, Universität Stuttgart, 1993.
49. (b) Steiner, R. P.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6861-6867.
50. Sawicki, E.; Hauser, T. R.; Stanley, T. W. Int. J. Air Pollul. 1960, 2, 253-272.
51. (a) Kaim, W.; Ernst, S.; Kohlmann, S. Chem. Unserer Zeit 1987, 21, 50-58.
52. (b) Lever, A. B. P. Inorganic Electronic Spectroscopy; Elsevier: Amsterdam, 1984.
53. (c) Scherer, O. J.; Schwalb, J.; Swarowsky, H.; Wolmershäuser, G.; Kaim, W.; Gross, R. Chem. Ber. 1988, 121, 443-449.
54. Heinze, J. Angew. Chem. 1984, 96, 823-840; Angew. Chem., Int. Ed. Engl. 1984, 23, 831-848.
55. Heinze, J. Angew. Chem. 1984, 96, 823-840; Angew. Chem., Int. Ed. Engl. 1984, 23, 831-848.
56. Wallis, J. M.; Kochi, J. K. J. Am. Chem. Soc. 1988, 110, 8207-8223.
57. Beck, F. Elektroorganische Chemie: Grundlagen und Anwendungen; Verlag Chemie: Weinheim. 1974; pp 103 and 208.
58. Pragst, F.; Santrucek, M. J. Prakt. Chem. 1987, 329, 67-80.
59. Shida, T. Electronic absorption spectra of radical ions (Physical sciences data 34): Elsevier: Amsterdam, 1988.
60. Hartschuh, A. Dissertation in preparation, Universität Stuttgart.
61. (a) Larsson, S.; Braga, M. Chem. Phys. 1993, 176, 367-375.
62. (b) Joachim, C., Launay, J. P.; Woitellier, S. Chem. Phys. 1990, 147, 131-141.
63. Ephardt, H.; Fromherz, P. J. Phys. Chem. 1991, 95, 6792-6797.
64. Anowski, S.; Voss, J. J. Prakt. Chem. 1996, 338, 337-344.
65. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259-271.
66. Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401-449.
67. Hanschuh, A.; Endtner, J. M. Unpublished results.
68. 0.0 transitions.
69. Handschuh, M.; Seibold, M.; Port, H.; Wolf, H. C. J. Phys. Chem. 1997, A101, 502-506.
70. Buu-Hoï, Ng. Ph.; Lavit, D.; Xuong, Ng. D. J. Chem. Soc. 1955, 1581-1583.