A novel redox switch for fluorescence: Drastic UV-vis and fluorescence spectral changes upon electrolysis of a hexaphenylethane derivative of 10,10′-dimethylbiacridan

Tetrahedron Letters

Volumn 44, Issue 36, 2003, Pages 6837-6840

  Suzuki, Takanori ^a   Migita, Akira ^a   Higuchi, Hiroki ^a   Kawai, Hidetoshi ^a   Fujiwara, Kenshu ^a   Tsuji, Takashi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Acridinium; Biacridan; Dication; Electrochromism; Electron donor; Fluorescence; Redox switch

Indexed keywords

10,10' DIMETHYLBIACRIDAN; ALKANE DERIVATIVE; HEXAPHENYLETHANE; METHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHROMATOPHORE; COLOR; ELECTROCHEMISTRY; ELECTROLYSIS; FLUORESCENCE; OXIDATION REDUCTION REACTION; ULTRAVIOLET RADIATION;

EID: 0042074143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01717-9     Document Type: Article

References (27)

1. Rurack K., Resch-Genger U. Chem. Soc. Rev. 31:2002;116.
2. Trautman J.K., Macklin J.J., Brus L.E., Betzig E. Nature. 369:1994;40.
3. Michaelis J., Hettich C., Mlynek J., Sandoghdr V. Nature. 405:2000;325.
4. Bergonzi R., Fabbrizzi L., Licchelli M., Mangano C. Coord. Chem. Rev. 170:1998;31.
5. Fabbrizzi L., Licchelli M., Pallavicini P. Acc. Chem. Res. 32:1999;846.
6. Li H., Jeppesen J.O., Levillain E., Becher J. Chem. Commun. 2003;846.
7. Suzuki, T.; Higuchi, H.; Tsuji, T.; Nishida, J.; Yamashita, Y.; Miyashi, T. In Chemistry of Namomolecular System. Chapter 1: Dynamic Redox Systems; Nakamura, T.; Matsumoto, T.; Tada, H.; Sugiura, K., Eds.; Springer-Verlag: Heidelberg, 2003; p. 3.
8. Fukuzumi S., Kitano T., Mochida K. J. Am. Chem. Soc. 112:1990;3246.
9. Fukuzumi S., Kitano T., Ishikawa M. J. Am. Chem. Soc. 112:1990;5631.
10. Fukuzumi S., Tokuda Y., Kitano T., Okamoto T., Otera J. J. Am. Chem. Soc. 115:1993;8960.
11. Huber C., Fähnrich K., Krause C., Werner T. J. Photochem. Photobiol. A128:1999;111.
12. Bock H., Sievert M., Havlas Z. Chem. Eur. J. 4:1998;677.
13. Gerhard M., Berndt S. Z. Naturforsch. B40:1985;90.
14. 3): δ/ppm: 7.36-7.24 (m, 8H), 7.17 (br. dd, 2H, J=7.5, 7.5 Hz), 7.00 (br. dd, 2H, J=7.5, 7.5 Hz), 6.87 (br. d, 2H, J=7.5 Hz), 6.84 (ddd, 2H, J=7.5, 7.5, 1.0 Hz), 6.77 (br. d, 2H, J=7.5 Hz), 6.73 (br. d, 2H, J=7.5 Hz), 6.51 (br. d, 2H, J=7.5 Hz), 6.37 (ddd, 2H, J=7.5, 7.5, 1.0 Hz), 5.06 (s, 2H), 3.36 (s, 6H).
15. Mader F., Zanker V. Chem. Ber. 97:1964;2418.
16. -1, T=153 K. The final R value is 0.041 for 4995 independent reflections with I>3σI and 379 parameters.
17. Baldridge K.K., Battersby T.R., Clark R.V., Siegel J.S. J. Am. Chem. Soc. 119:1997;7048.
18. Suzuki T., Ono K., Nishida J., Takahashi H., Tsuji T. J. Org. Chem. 65:2000;4944.
19. Suzuki T., Ono K., Kawai H., Tsuji T. J. Chem. Soc., Perkin Trans. 2. 2001;1798.
20. Preuss J., Zanker V. Acta Crystallogr. B33:1977;2317.
21. Hounshell W.D., Dougherty D.A., Hummel J.P., Mislow K. J. Am. Chem. Soc. 99:1977;1916.
22. Maslak P., Narvaez J.N., Vallombroso T.M. Jr. J. Am. Chem. Soc. 117:1995;12373.
23. em 510 nm) exhibits the similar red shift (Ref. 19).
24. Jonker S.A., Ariese F., Verhoeven J.W. Recl. Trav. Chim. Pays-Bas. 108:1989;109.
25. Suzuki T., Nishida J., Tsuji T. Chem. Commun. 1998;2193.
26. Lu W., Gao J.P., Wang Z.Y., Qi Y., Sacripante G.G., Duff J.D., Sundararajan P.R. Macromolecules. 32:1999;8880.
27. Quinto M., Bard A.J. J. Electroanal. Chem. 498:2001;67.