SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1545 - 1550

DOI: https://doi.org/10.6023/cjoc201301002

Notes

A Novel Triad Fluorescent Chemodosimeter with 4,5-Bis(2’-cyano-ethylthio)-1,3-dithiole-2-thione and Anthracene Units for Hg(II) Recognition and Its Fluorescence Properties in Ionic Liquid

  • Chi Xingbao ,
  • Liu Yang
Expand
  • School of Chemistry and Material Science, Huaibei Normal University, Huaibei 235000

Received date: 2013-01-02

  Revised date: 2013-02-05

  Online published: 2013-03-07

Supported by

Project supported by Natural Science Foundation of Anhui Province Institution of Higher Learning (No. KJ2010A307) and the Foundation of Science and Technology Talent of Huaibei City (No.20120310).

Fold

Abstract

4,5-Bis(2'-cyanoethylthio)-1,3-dithiole-2-thione (DMIT) was treated with sodium methoxide to deprotect one 2-cyanoethyl group, affording mono-thiolate of DMIT. The generated mono-thiolate was trapped by 9,10-dicholormethylene anthracene to yield a novel triad fluorescent chemodosimeter with DMIT and anthracene units. The triad reacted with Hg(OAc)2 to yield a strongly fluorescent compound 4 and a complex 5 of DMIT. So the triad could selectively recognize Hg2+ by the unique properties of compound 4. Fluorescence properties of the triad were further explored in ionic liquid. The experiment results showed that fluorescence intensity of the triad became more strengthen with amounts of ionic liquid.

Key words： 1,3-dithiole-2-thione; fluorescent chemodosimeter; synthesis; ionic liquid

Cite this article

Chi Xingbao , Liu Yang . A Novel Triad Fluorescent Chemodosimeter with 4,5-Bis(2’-cyano-ethylthio)-1,3-dithiole-2-thione and Anthracene Units for Hg(II) Recognition and Its Fluorescence Properties in Ionic Liquid[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1545 -1550 . DOI: 10.6023/cjoc201301002

References

[1] (a) De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515. (b) Fabbrizzi, L.; Licchelli, M.; Pallavicini, P. Acc. Chem. Res. 1999, 32, 846. (c) Feringa, B. L. Molecular Switches, Wiley-VCH, Weinheim, Germany, 2001. (d) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348.
[2] Callan, J. F.; De Silva, A. P.; McClenaghan, N. D. Chem. Commun. 2004, 2048.
[3] Uchiyama, S.; Kawai, N.; de Silva, A. P.; Iwai, K. J. Am. Chem. Soc. 2004, 126, 3032.
[4] (a) Gobbi, L.; Seiler, P.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 674. (b) Beyeler, A.; Belser, P.; De Cola, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 2779.
[5] (a) Fabbrizzi, L.; Licchelli, M.; Mascheroni, S.; Poggi, A.; Sacchi, D.; Zema, M. Inorg. Chem. 2002, 41, 6129. (b) De Santis, G.; Fabbrizzi, L.; Licchelli, M.; Sardone, N.; Velders, A. H. Chem. Eur. J. 1996, 2, 1243.
[6] (a) De Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. J. Am. Chem. Soc. 1997, 119, 7891. (b) Zhang, G.-X.; Zhang, D.-Q.; Yin, S.-W.; Yang, X.-D.; Shuai, Z.-G.; Zhu, D.-B. Chem. Commun. 2005, 2161.
[7] (a) Albelda, M. T.; Bernardo, M. A.; Dÿaz, P.; Garcÿa-España, E.; Seixas de Melo, J.; Pina, F.; Soriano, C.; Luis, S. V. Chem. Commun. 2001, 1520. (b) Qu, D.-H.; Wang, Q.-C.; Ren, J.; Tian, H. Org. Lett. 2004, 6, 2085.
[8] (a) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348. (b) Jongmin, K.; Miwhoa, C. J.; Young, K.; Eun, Y. L.; Juyoung, Y. J. Org. Chem. 2002, 67, 4384. (c) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecular Recognition, American Chemical Society, Washington, DC, 1992. (d) De Silva, S. A.; Amorelli, B.; Isidor, D. C.; Loo, K. C.; Crooker, K. E.; Pena, Y. E. Chem. Commun. 2002, 1360. (e) Zhou, G.; Cheng, Y.-X.; Wang, L.-X.; Jing, X.-B.; Wang, F.-S. Macromolecules 2005, 38, 2148.
[9] Simonesn, K. B.; Svenstrup, N.; Lau, J.; Simonsen, O.; Mørk, P.; Kristensen, G. J.; Becher, J. Synthesis 1996, 407.
Options
Outlines

/

〈 〉