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

doi:10.6023/cjoc201301002

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1545-1550.DOI: 10.6023/cjoc201301002 Previous Articles Next Articles

Notes

蒽单元和1,3-二硫杂环戊烯-2-硫酮单元构建的三组分荧光传感器与汞(II)的反应及其在离子液中的荧光性质

迟兴宝, 刘洋

淮北师范大学化学与材料科学学院淮北 235000

收稿日期:2013-01-02 修回日期:2013-02-05 发布日期:2013-03-07
通讯作者: 迟兴宝 E-mail:chxbao@126.com
基金资助:
安徽高校省级自然科学研究重点项目计划(No. KJ2010A307);淮北市科技人才培育计划基金(No. 20120310)资助项目.

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

School of Chemistry and Material Science, Huaibei Normal University, Huaibei 235000

Received:2013-01-02 Revised:2013-02-05 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).

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]. Chin. J. Org. Chem., 2013, 33(07): 1545-1550.

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[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.

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蒽单元和1,3-二硫杂环戊烯-2-硫酮单元构建的三组分荧光传感器与汞(II)的反应及其在离子液中的荧光性质

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

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