Journal of Fluorescence

, Volume 24, Issue 4, pp 1347–1355 | Cite as

Detection of HSO4 Ion Based on the Hydrolysis of Diketopyrrolopyrrole-derived Schiff Base with Chromogenic and Fluorogenic Dual Signals

  • Lingyun Wang
  • Lingling Yang
  • Derong Cao


A new diketopyrrolopyrrole-based Schiff base L was synthesized and its anion sensing behavior was explored. L showed exclusive response toward HSO4 ion and also distinguished HSO4 from other anions by color changes (from dark red to orange) and 21 fold fluorescence enhancement at 370 nm in aqueous solution (THF/H2O = 8/1, v/v). The sensing mechanism was suggested to proceed via a hydrolysis process. The results provided colorimetric and fluorimetric assays to selectively detect the presence of a HSO4 over a wide range of other interfering anions. The results could potentially be used as a dual colorimetric-fluorescent probe for monitoring HSO4 levels in physiological and environmental systems.


HSO4 Schiff base Colorimetric Fluorescent Hydrolysis 



The supports by National Natural Science Foundation of China (No. 21274045), the Pearl River in Guangzhou city of Nova of Science and Technology Special Funded Projects (No. 2012J2200009), the Fundamental Research Funds for the Central Universities (2013ZZ067), the Natural Science Foundation of Guangdong Province (10351064101000000) and National Basic Research Program of China (2012CB720801) are gratefully acknowledged.

Supplementary material

10895_2014_1421_MOESM1_ESM.doc (630 kb)
ESM 1 (DOC 630 kb)


  1. 1.
    Shao J, Lin H, Lin HK (2008) Talanta 75:1015–1020PubMedCrossRefGoogle Scholar
  2. 2.
    Khanmohammadi H, Rezaeian K (2014) RSC Adv 4:1032–1038CrossRefGoogle Scholar
  3. 3.
    Mahapatra AK, Maji R, Maiti K, Adhhikari SS, Mukhopadhyay CD, Mandal D (2014) Analyst 139:309–317PubMedCrossRefGoogle Scholar
  4. 4.
    Li Q, Yue Y, Guo Y, Shao SJ (2012) Sensors Actuators B 173:797–801CrossRefGoogle Scholar
  5. 5.
    Alfonso M, Tárraga A, Molina P (2011) Org Lett 13:6432–6435PubMedCrossRefGoogle Scholar
  6. 6.
    Chawla HM, Sahu SN, Shrivastava R (2007) Tetrahedron Lett 48:6054–6058CrossRefGoogle Scholar
  7. 7.
    Zhou LL, Sun H, Li HP, Wang H, Zhang XH, Wu SK, Lee ST (2004) Org Lett 6:1071–1074PubMedCrossRefGoogle Scholar
  8. 8.
    Li P, Zhang YM, Lin Q, Li JQ, Wei TB (2012) Spectrochim Acta Part (A) 90:152–157CrossRefGoogle Scholar
  9. 9.
    Xue WJ, Li L, Li Q, Wu AX (2012) Talanta 88:734–738PubMedCrossRefGoogle Scholar
  10. 10.
    Tan CL, Wang QM (2011) Inorg Chem 50:2953–2956PubMedCrossRefGoogle Scholar
  11. 11.
    Jeon NJ, Ryu BJ, Park KD, Lee YJ, Nam KC (2010) Chem Soc 31:3809–3811Google Scholar
  12. 12.
    Kaur P, Kaur H, Singh K (2013) Analyst 138:425–428PubMedCrossRefGoogle Scholar
  13. 13.
    Song NR, Moon JH, Choi J, Jun EJ, Kim Y, Kim SJ, Lee JY, Yoon J (2013) Chem Sci 4:1765–1771CrossRefGoogle Scholar
  14. 14.
    Sessler JL, Katayev E, Pantos GD, Ustynyuk YA (2004) Chem Commun 40:1276–1277Google Scholar
  15. 15.
    Nam KC, Kang SO (1999) Tetrahedron Lett 40:7343–7346CrossRefGoogle Scholar
  16. 16.
    Kang SO, Day VW, James KB (2009) Org Lett 11:3654–3657PubMedCrossRefGoogle Scholar
  17. 17.
    Kaur K, Bhardwaj VK, Kaur N, Singh N (2012) Inorg Chem Commun 18:79–82CrossRefGoogle Scholar
  18. 18.
    Huang G, Zhang G, Zhang D (2012) Chem Commun 48:7504–7506CrossRefGoogle Scholar
  19. 19.
    Alfonso M, Espinosa A, Tárraga A, Molina P (2012) Chem Commun 48:6848–6850CrossRefGoogle Scholar
  20. 20.
    Kim HJ, Bhuniya S, Mahajan RK, Puri R, Liu HG, Ko KC, Lee JY, Kim JS (2009) Chem Commun:7128–7130Google Scholar
  21. 21.
    Kumar V, Kumar A, Diwan U, Upadhyay KK (2012) Chem Commun 48:9540–9542CrossRefGoogle Scholar
  22. 22.
    Lin CY, Huang KF, Yen YP (2013) Spectrochim Acta Part (A) 115:552–558CrossRefGoogle Scholar
  23. 23.
    Katayev EA, Ustynyuk YA, Sessler JL (2006) Coord Chem Rev 250:3004–3037CrossRefGoogle Scholar
  24. 24.
    Deng L, Wu WT, Guo HM, Zhao JZ, Ji SM, Zhang X, Yuan XL, Zhang CL (2011) J Org Chem 76:9294–9304PubMedCrossRefGoogle Scholar
  25. 25.
    Kaur M, Yang DS, Choi K, Cho MJ, Choi DH (2014) Dyes Pigments 100:118–126CrossRefGoogle Scholar
  26. 26.
    Zhang G, Bi S, Song L, Wang F, Yu J, Wang L (2013) Dyes Pigments 99:779–786CrossRefGoogle Scholar
  27. 27.
    Qu Y, Hua JL, Tian H (2010) Org Lett 12:3320–3323PubMedCrossRefGoogle Scholar
  28. 28.
    Qu Y, Qu S, Yang L, Hua JL, Qu DH (2012) Sensors Actuators B 173:225–233CrossRefGoogle Scholar
  29. 29.
    Ramakrishnam MV, Lin HC (2013) Org Lett 15:1274–1277CrossRefGoogle Scholar
  30. 30.
    Ftouni H, Bolze F, Rocquigny HD, Nicoud JF (2013) Bioconjug Chem 24:942–950PubMedCrossRefGoogle Scholar
  31. 31.
    Zhou E, Yamakawa S, Tajima K, Yang CH, Hashimoto K (2009) Chem Mater 21:4055–4061CrossRefGoogle Scholar
  32. 32.
    Jin Y, Xu YB, Liu YL, Wang LY, Jiang HF, Li XJ, Cao DR (2011) Dyes Pigments 90:311–318CrossRefGoogle Scholar
  33. 33.
    Tong C, Xiang G, Lumin J (2007):575–580Google Scholar
  34. 34.
    Jung HS, Han JH, Kim ZH, Kang C, Kim JS (2011) Org Lett 13:5056–5059PubMedCrossRefGoogle Scholar
  35. 35.
    Lee MH, Giap TV, Kim SH, Lee YH, Kang C, Kim JS (2010) Chem Commun 46:1407–1409CrossRefGoogle Scholar
  36. 36.
    Jung HS, Han JH, Habata Y, Kang C, Kim JS (2011) Chem Commun 47:5142–5144CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhouChina

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