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A diarylethene-derived probe for colorimetric detection of CN− and highly selective fluorescent recognition of I−

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Abstract

A new photochromic diarylethene derivative with 2-hydrazinobenzothiazole was synthesized, and its multi-controllable switch behavior was investigated in detail when triggered by light and anions. When triggered by CN−, the absorption spectra of the diarylethene showed a new band at 474 nm with an obvious color change from colorless to bright yellow. Upon addition of I−, the diarylethene compound displayed a new absorption band at 297 nm and the original absorption at 370 nm also increased, and the fluorescence intensity exhibited obvious fluorescence quenching with fluorescence color change from a light royal blue to dark. The results indicated that the diarylethene derivative exhibited naked-eye detection of CN− and the fluorescent recognition of I−.

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Notes and references

  1. V. Amendola, D. Esteban-Gomez, L. Fabbrizzi and M. Licchelli, Acc. Chem. Res., 2006, 39, 343–353

    Article  CAS  PubMed  Google Scholar 

  2. Y. Zhou, J. F. Zhang and J. Yoon, Chem. Rev., 2014, 114, 5511–5571

    Article  CAS  PubMed  Google Scholar 

  3. P. A. Gale, S. E. Garcia-Garrido and J. Garric, Chem. Soc. Rev., 2008, 37, 151–190

    Article  CAS  PubMed  Google Scholar 

  4. Y. Zhou, Z. C. Xu and J. Yoon, Chem. Soc. Rev., 2011, 40, 2222–2235

    Article  CAS  PubMed  Google Scholar 

  5. A. G. Gilman, L. S. Goodman, T. W. Rad and F. Murad, The Pharmacological Basis of Therapeutics, Macmillan, New York, 7th edn, 1985, p. 964

    Google Scholar 

  6. G. Aumont and J. C. Tressol, Analyst, 1986, 111, 841–843

    Article  CAS  PubMed  Google Scholar 

  7. M. Haldimann, B. Zimmerli, C. Als and H. Gerber, Clin. Chem., 1998, 44, 817–824

    Article  CAS  PubMed  Google Scholar 

  8. P. A. Lyday, in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000

    Google Scholar 

  9. A. K. Singh and S. Mehtab, Talanta, 2008, 74, 806–814

    Article  CAS  PubMed  Google Scholar 

  10. C. Young, L. Tidwell and C. Anderson, Cyanide: Social Industrial and Economic Aspects, Minerals, Metals, and Materials Society, Warrendale, 2001

    Google Scholar 

  11. K. W. Kulig, Cyanide Toxicity, U.S. Department of Health and Human Services, Atlanta, GA, 1991

    Google Scholar 

  12. S. I. Baskin and T. G. Brewer, Medical Aspects of Chemical and Biological Warfare, ed. F. Sidell, E. T. Takafuji and D. R. Franz, TMM Publication, Washington, DC, 1997, ch. 10, pp. 271-286

  13. S. P. Franz and B. Michael, Chem. Rev., 1997, 97, 1609–1646

    Article  Google Scholar 

  14. N. H. Evans and P. D. Beer, Angew. Chem., Int. Ed., 2014, 53, 11716–11754

    Article  CAS  Google Scholar 

  15. K. Higashiguchi, K. Matsuda, N. Tanifuji and M. Irie, J. Am. Chem. Soc., 2005, 127, 8922–8923

    Article  CAS  PubMed  Google Scholar 

  16. N. Tanifuji, M. Irie and K. Matsuda, J. Am. Chem. Soc., 2005, 127, 13344–13353

    Article  CAS  PubMed  Google Scholar 

  17. A. Peters and N. R. Branda, J. Am. Chem. Soc., 2003, 125, 3404–3405

    Article  CAS  PubMed  Google Scholar 

  18. Y. Moriyama, K. Matsuda, N. Tanifuji, S. Irie and M. Irie, Org. Lett., 2005, 7, 3315–3318

    Article  CAS  PubMed  Google Scholar 

  19. Q. Zou, X. Li, J. J. Zhang, J. Zhou, B. B. Sun and H. Tian, Chem. Commun., 2012, 48, 2095–2097

    Article  CAS  Google Scholar 

  20. C. C. Zhang, S. Z. Pu, Z. Y. Sun, C. B. Fan and G. Liu, J. Phys. Chem. B, 2015, 119, 4673–4682

    Article  CAS  PubMed  Google Scholar 

  21. H. Tian and S. Wang, Chem. Commun., 2007, 781–792

    Google Scholar 

  22. M. Irie, Chem. Rev., 2000, 100, 1685–1716

    Article  CAS  PubMed  Google Scholar 

  23. T. Shiozawa, M. K. Hossain, T. Ubukata and Y. Yokoyama, Chem. Commun., 2010, 46, 4785–4787

    Article  CAS  Google Scholar 

  24. M. Irie, S. Kobatake and M. Horichi, Science, 2001, 291, 1769–1772

    Article  CAS  PubMed  Google Scholar 

  25. S. Q. Cui, G. Liu, S. Z. Pu and B. Chen, Dyes Pigm., 2013, 99, 950–956

    Article  CAS  Google Scholar 

  26. H. C. Ding, G. Liu, S. Z. Pu and C. H. Zheng, Dyes Pigm., 2014, 103, 82–88

    Article  CAS  Google Scholar 

  27. S. H. **g, C. H. Zheng, S. Z. Pu, C. B. Fan and G. Liu, Dyes Pigm., 2014, 107, 38–44

    Article  CAS  Google Scholar 

  28. S. Z. Pu, L. L. Ma, G. Liu, H. C. Ding and B. Chen, Dyes Pigm., 2015, 113, 70–77

    Article  CAS  Google Scholar 

  29. F. Hu, M. Cao, X. Ma, S. H. Liu and J. Yin, J. Org. Chem., 2015, 80, 7830–7835

    Article  CAS  PubMed  Google Scholar 

  30. Z. G. Zhou, S. Z. **ao, J. Xu, Z. Q. Liu, M. Shi, F. Y. Li, T. Yi and C. H. Huang, Org. Lett., 2006, 8, 3911–3914

    Article  CAS  PubMed  Google Scholar 

  31. H. J. Jia, S. Z. Pu, C. B. Fan, G. Liu and C. H. Zheng, Dyes Pigm., 2015, 121, 211–220

    Article  CAS  Google Scholar 

  32. P. Thiampanya, N. Muangsin and B. Pulpoka, Org. Lett., 2012, 14, 4050–4053

    Article  CAS  PubMed  Google Scholar 

  33. B. G. Zhang, J. Xu, Y. G. Zhao, C. Y. Duan, X. Cao and Q. J. Meng, Dalton Trans., 2006, 1271–1276

    Google Scholar 

  34. S. Q. Cui, S. Z. Pu, W. J. Liu and G. Liu, Dyes Pigm., 2011, 91, 435–441

    Article  CAS  Google Scholar 

  35. P. P. Ren, R. J. Wang, S. Z. Pu, G. Liu and C. B. Fan, J. Phys. Org. Chem., 2014, 27, 183–190

    Article  CAS  Google Scholar 

  36. V. W.-W. Yam, J. K.-W. Lee, C.-C. Ko and N. Zhu, J. Am. Chem. Soc., 2009, 131, 912–913

    Article  CAS  PubMed  Google Scholar 

  37. M. Irie, T. Lifka, S. Kobatake and N. Kato, J. Am. Chem. Soc., 2000, 122, 4871–4876

    Article  CAS  Google Scholar 

  38. A. Fihey, A. Perrier, W. R. Browne and D. Jacquemin, Chem. Soc. Rev., 2015, 44, 3719–3759

    Article  CAS  PubMed  Google Scholar 

  39. J. J. Zhang, Q. Zou and H. Tian, Adv. Mater., 2013, 25, 378–399

    Article  CAS  PubMed  Google Scholar 

  40. K. I. Hong, H. Yoon and W. D. Jang, Chem. Commun., 2015, 51, 7486–7488

    Article  CAS  Google Scholar 

  41. A. Kumar and H.-S. Kim, New J. Chem., 2015, 39, 2935–2942

    Article  CAS  Google Scholar 

  42. N. Boens, V. Leen and W. Dehaen, Chem. Soc. Rev., 2012, 41, 1130–1172

    Article  CAS  PubMed  Google Scholar 

  43. Q. T. Meng, Y. Shi, C. P. Wang, H. M. Jia, X. Gao, R. Zhang, Y. F. Wang and Z. Q. Zhang, Org. Biomol. Chem., 2015, 13, 2918–2926

    Article  CAS  PubMed  Google Scholar 

  44. L. Y. Wang, G. P. Fang, D. Ye and D. Cao, Sens. Actuators, B, 2014, 195, 572–580

    Article  CAS  Google Scholar 

  45. Y. T. Chen, Y. S. Mi, Q. F. **e, J. N. **ang, H. L. Fan, X. B. Luo and S. R. **a, Anal. Methods, 2013, 5, 4818

    Article  CAS  Google Scholar 

  46. X. Wu, J. Chen and J. X. J. Zhao, Analyst, 2013, 138, 5281–5287

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, 330013, P. R. China

    X. G. Tang, H. L. Liu & S. Z. Pu

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  1. X. G. Tang
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  2. H. L. Liu
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  3. S. Z. Pu
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Correspondence to H. L. Liu or S. Z. Pu.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c6pp00104a

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Tang, X.G., Liu, H.L. & Pu, S.Z. A diarylethene-derived probe for colorimetric detection of CN− and highly selective fluorescent recognition of I−. Photochem Photobiol Sci 15, 1579–1585 (2016). https://doi.org/10.1039/c6pp00104a

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