1,3-Dithiole-2-thione derivatives featuring an anthracene unit: New selective chemodosimeters for Hg(II) ion

Chemical Communications

Volumn , Issue 16, 2005, Pages 2161-2163

  Zhang, Guanxin ^a,b   Zhang, Deqing ^a   Yin, Shiwei ^a,b   Yang, Xiaodi ^a,b   Shuai, Zhigang ^a   Zhu, Daoben ^a  

^a Institute of Chemistry   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DITHIOLE 2 THIONE DERIVATIVE; 1,3 DITHIOLE DERIVATIVE; 4 [2 (9 ANTHRYLOXY)ETHYL]THIO 1,3 DITHIOLE 2 THIONE; 4 [2 (9 ANTHRYLOXY)ETHYL]THIO 5 (2 CYANOETHYLTHIO) 1,3 DITHIOL 2 ONE; 4 [2 (9 ANTHRYLOXY)ETHYL]THIO 5 (2 CYANOETHYLTHIO) 1,3 DITHIOLE 2 THIONE; ANTHRACENE DERIVATIVE; BARIUM ION; COBALT; FERRIC ION; LEAD; MANGANESE; MERCURY; NICKEL; SILVER; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG; ZINC ION;

AQUEOUS SOLUTION; ARTICLE; CHEMODOSIMETER; DOSIMETER; ELECTRON TRANSPORT; ENERGY TRANSFER; FLUORESCENCE; FLUORESCENCE RESONANCE ENERGY TRANSFER; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; POLLUTION MONITORING; QUANTUM YIELD; SOLUBILITY; THIN LAYER CHROMATOGRAPHY; WATER CONTAMINATION;

EID: 18544378600     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417952h     Document Type: Article

References (27)

1. (a) A. Renzoni, F. Zino and E. Franchi, Environ. Res., 1998, 77, 68-72
2. (b) O. Malm, Environ. Res., 1998, 77, 73-78.
3. P. Grandjean, P. Heihe, R. F. White and F. Debes, Environ. Res., 1998, 77, 165-172.
4. (a) A. B. Descalzo, R. Martinez-Máñez, R. Radeglia, K. Rurack and J. Soto, J. Am. Chem. Soc., 2003, 125, 3418-3419
5. (b) X.-B. Zhang, C.-C. Guo, Z.-Z. Li, G.-L. Shen and R.-Q. Yu, Anal. Chem., 2002, 74, 821-825
6. (c) A. Ono and H. Togashi, Angew. Chem. Int. Ed., 2004, 43, 4300-4302
7. (d) K. Rurack, M. Kollmannsberger, U. Resch-Genger and J. Daub, J. Am. Chem. Soc., 2000, 122, 968-969
8. (e) K. Rurack, U. Resch-Genger, J. L. Bricks and M. Spieles, Chem. Commun., 2000, 2103-2104
9. (f) L. Prodi, C. Bargossi, M. Montalti, N. Zaccheroni, N. Su, J. S. Bradshaw, R. M. Izatt and P. B. Savage, J. Am. Chem. Soc., 2000. 122, 6769-6770
10. (g) H. Sakamoto, J. Ishikawa, S. Nakao and H. Wada, Chem. Commun., 2000, 2395-2396
11. (h) D. Y. Sasaki and B. E. Padilla, Chem. Commun., 1998, 1581-1582
12. (i) E. M. Nolan and S. J. Lippard, J. Am. Chem. Soc., 2003, 125, 14270-14271
13. (j) E. Palomares, R. Vilar and J. R. Durrant, Chem. Commun., 2004, 362-363
14. (k) X. F. Guo, X. H. Qian and L. H. Jia. J. Am. Chem. Soc., 2004, 126, 2272-2273.
15. M. Y. Chea and A. W. Czarnik, J. Am. Chem. Soc., 1992, 114, 9704-9705.
16. (a) G. Zhang, D. Zhang, X. Guo and D. Zhu, Org. Lett., 2004, 6, 1209-1212
17. (b) X. Li, G. Zhang, H. Ma, D. Zhang, J. Li and D. Zhu, J. Am. Chem. Soc., 2004, 126, 11543-11548
18. (c) G. Zhang, X. Li, H. Ma. D. Zhang, J. Li and D. Zhu, Chem. Commun., 2004, 18, 2072-2073.
19. The synthesis and characterization of compounds 1, 3 and 4 are described in the Electronic Supplementary Information.
20. The fluorescence quantum yields were determined by using 9,10-diphenylanthracene in THF as a reference.
21. (a) C. Jia, D. Zhang, W. Xu and D. Zhu, Org. Lett., 2001, 3, 1941
22. (b) C. Jia, D. Zhang, X. Guo, S. Wan, W. Xu and D. Zhu, Synthesis, 2002, 15, 2177.
23. The results of the preliminary theoretical calculation with compounds 6 and 7 (see ES1) indicate that compound 6 shows strong absorption at longer wavelength compared with compound 7. Moreover, the calculation results also show that the HOMO energy of compound 6 is higher than that of compound 7, which is in agreement with the fact that compound 6 shows lower oxidation potential than compound 7.
24. 2/εr = -0.1 eV. see (a) D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 259.
25. (b) Z. R. Grabowski and J. Dobkowski, Pure Appl. Chem., 1983, 55, 245.
26. (a) F. Challenger, E. A. Mason, E. C. Holdsworth and R. Enimott, J. Chem. Soc., 1953, 292
27. (b) see Ref. 4.