A new 4-(N,N-dimethylamino)benzonitrile (DMABN) derivative with tetrathiafulvalene unit: modulation of the dual fluorescence of DMABN by redox reaction of tetrathiafulvalene unit

Tetrahedron Letters

Volumn 49, Issue 8, 2008, Pages 1361-1364

  Tan, Wei ^a,b   Zhang, Deqing ^a   Wu, Hui ^a,b   Zhu, Daoben ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

DMABN; Fluorescence switch; Tetrathiafulvalene; TICT

Indexed keywords

4 DIMETHYLAMINOBENZONITRILE; BENZONITRILE; FERRIC ION; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; FLUORESCENCE; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 38349157778     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.087     Document Type: Article

References (32)

1. Lippert E., Lüder W., Moll F., Nagele H., Boos H., Prigge H., and Siebold-Blankenstein I. Angew. Chem. 73 (1961) 695
2. Rettig W. Angew. Chem., Int. Ed. Engl. 25 (1986) 971 and references therein
3. Rotkiewicz K., Grellmann K.H., and Grabowski Z.R. Chem. Phys. Lett. 19 (1973) 315
4. Grabowski Z.R., Rotkiewicz K., and Rettig W. Chem. Rev. 103 (2003) 3899 and references therein
5. Rettig W., Bliss B., and Dirnberger K. Chem. Phys. Lett. 305 (1999) 8
6. Rettig W., and Zietz B. Chem. Phys. Lett. 317 (2000) 187
7. Rettig W., and Lutze S. Chem. Phys. Lett. 341 (2001) 263
8. Dobkowski J., Wójcik J., Kozminski W., Kolos R., Waluk J., and Michl J. J. Am. Chem. Soc. 124 (2002) 2406
9. Rappoport D., and Furche F. J. Am. Chem. Soc. 126 (2004) 1277
10. Jamorski Jodicke C., and Luthi H.P. J. Am. Chem. Soc. 125 (2003) 252
11. Mennucci B., Toniolo A., and Tomasi J. J. Am. Chem. Soc. 122 (2000) 10621
12. Wu F.Y., and Jiang Y.B. Chem. Phys. Lett. 355 (2002) 438
13. Wu F.Y., Ma L.H., and Jiang Y.B. Anal. Sci. 17 (2001) i801
14. Wu F.Y., Li Z., Wen Z.C., Zhou N., Zhao Y.F., and Jiang Y.B. Org. Lett. 4 (2002) 3203
15. Wen Z.C., and Jiang Y.B. Tetrahedron 60 (2004) 11109
16. Collins G.E., Choi L.S., and Callahan J.H. J. Am. Chem. Soc. 120 (1998) 1474
17. Tan W., Zhang D.Q., Wang Z., Liu C.M., and Zhu D.B. J. Mater. Chem. 17 (2007) 1964
18. Tan W., Zhang D.Q., and Zhu D.B. Bioorg. Med. Chem. Lett. 17 (2007) 2629
19. Jørgensen T., Hansen T.K., and Becher J. Chem. Soc. Rev. 23 (1994) 41
20. Nielsen M.B., and Becher J. Liebigs Ann. Recl. (1997) 2177
21. In: Yamada J., and Sugimoto T. (Eds). TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalene (2004), Kodansha-Springer, Tokyo and references therein
22. Bendikov M., Wudl F., and Perepichka D.F. Chem. Rev. 104 (2004) 4891
23. Bryce M.R. Adv. Mater. 11 (1999) 11
24. Segura J.L., and Martín N. Angew. Chem., Int. Ed. 40 (2001) 1372
25. Gorgues A., Hudhomme P., and Sallé M. Chem. Rev. 104 (2004) 5151
26. Zhou Y.C., Wu H., Qu L., Zhang D.Q., and Zhu D.B. J. Phys. Chem. B 110 (2006) 15676
27. Zhang G.X., Zhang D.Q., Guo X.F., and Zhu D.B. Org. Lett. 6 (2004) 1209
28. Zhou Y.C., Zhang D.Q., Zhu L.Y., Shuai Z.G., and Zhu D.B. J. Org. Chem. 71 (2006) 2123
29. Spanggaard H., Prehn J., Nielsen M.B., Levillain E., Allain M., and Becher J. J. Am. Chem. Soc. 122 (2000) 9486
30. +): 485.9515; found: 485.9520.
31. 3+ were added, typical absorption bands for the dication of TTF unit were observed. The fluorescence intensities of both A band and B band decreased slightly.
32. 2 (ox) (vs Ag/AgCl) = 0.93 V were detected for compound 1.