Journal of Fluorescence

, Volume 23, Issue 1, pp 21–29 | Cite as

Study on the Selectivity of Anion Receptors Based on Similar (thio)urea Fragments

  • Weiwei Huang
  • Zhongyue Yang
  • Hai Lin
  • Huakuan Lin


Three new selective anion receptors containing the (thio)urea binding sites were developed, Indole-3-formaldehyde phenyl-semithiocarbazone, Indole-3-formaldehyde nitrophenyl-semithiocarbazone, and Indole-3-formaldehyde nitrophenyl-semicarbazone, nominated as receptors 1, 2 and 3, respectively. Receptor 1 shows high selective recognition for F only, while both receptor 2 and receptor 3 containing a p-nitro group show high selective recognition for AcO. The high selective recognition of these receptors to anions is further investigated by X-ray crystallography diffraction, UV-vis, fluorescence analyses and 1H NMR. Furthermore, receptor 2 changes from yellow to orange, and receptor 3 darkens when acetate is added, providing a way of detection by ‘naked-eye’.


Fluoride ion Acetate Anion recognition Colorimetric Naked-eye 



This project was supported by the National Natural Science Foundation of China (20371028, 20671052).

Supplementary material

10895_2012_1110_MOESM1_ESM.doc (157 kb)
ESM 1 (DOC 157 kb)


  1. 1.
    Gunnlaugsson T, Glynn M, Tocci GM, Kruger PE, Pfeffer FM (2006) Coord Chem Rev 250:3094–3117CrossRefGoogle Scholar
  2. 2.
    Gale PA, Garcia-Garrido SE, Garric J (2008) Chem Soc Rev 37:151–190PubMedCrossRefGoogle Scholar
  3. 3.
    Dreisbuch RH (1980) Handbook of poisoning. Lange Medical Publishers, Los AltosGoogle Scholar
  4. 4.
    Gunnlaugsson T, Davis AP, O’Brien JE, Glynn M (2002) Org Lett 4:2449–2452PubMedCrossRefGoogle Scholar
  5. 5.
    Schumacher AL, Hill JP, Ariga K, D’Souza F (2007) Electrochem Commun 9:2751–2754CrossRefGoogle Scholar
  6. 6.
    Jose DA, Kumar DK, Kar P, Verma S, Ghosh A, Ganguly B, Ghosh HN, Das A (2014) Tetrahedron 63(2007):12007–12014Google Scholar
  7. 7.
    Moon KS, Singh N, Lee GW, Jang DO (2007) Tetrahedron 63:9106–9111CrossRefGoogle Scholar
  8. 8.
    Joo TY, Singh N, Lee GW, Jang DO (2007) Tetrahedron Lett 48:8846–8850CrossRefGoogle Scholar
  9. 9.
    Zhang YH, Yin ZM, He JQ, Cheng JP (2007) Tetrahedron Lett 48:6039–6043CrossRefGoogle Scholar
  10. 10.
    Maeda H, Ito Y (2006) Inorg Chem 45:8205–8210PubMedCrossRefGoogle Scholar
  11. 11.
    Shao J, Wang YH, Lin H, Li JW, Lin HK (2008) Sens Actuator B 134:849–853CrossRefGoogle Scholar
  12. 12.
    Priyadip D, Prasenjit M, Amrita G, Amal KM, Tanmayanerjee B, Sukdeb S, Amitava D (2011) J Chem Sci 123:175–186CrossRefGoogle Scholar
  13. 13.
    Martinez-Manez R, Sancenon F (2003) Chem Rev 103:4419–4476PubMedCrossRefGoogle Scholar
  14. 14.
    Martinez-Manez R, Sancenon F (2006) Coord Chem Rev 250:3081–3093CrossRefGoogle Scholar
  15. 15.
    Shao J, Lin H, Yu M, Lin HK (2008) Talanta 75:551–555PubMedCrossRefGoogle Scholar
  16. 16.
    Shao J, Lin H, Shang XF, Chen HM, Lin HK, Inclusion Phenom J (2007) Mol Recognit Chem 59:371–375CrossRefGoogle Scholar
  17. 17.
    Gunnlaugsson T, Davis AP, Glynn M (2001) Chem Commun 2556–2557Google Scholar
  18. 18.
    Gunnlaugsson T, Kruger PE, Lee TC, Parkesh R, Pfeffer FM, Hussey GM (2003) Tetrahedron Lett 44:6575–6578CrossRefGoogle Scholar
  19. 19.
    Han F, Bao YH, Yan YH, Fyles TM, Hao JZ, Peng XJ, Fan JL, Wu YK, Sun SG (2007) Chem Eur J 13:2880–2892PubMedCrossRefGoogle Scholar
  20. 20.
    Lee DH, Im JH, Lee JH, Hong JI (2002) Tetrahedron Lett 43:9637–9640CrossRefGoogle Scholar
  21. 21.
    Watanabe S, Onogawa O, Komatsu Y, Yoshida K (1998) J Am Chem Soc 120:229–230CrossRefGoogle Scholar
  22. 22.
    Liu Y, You CC, Zhang HY (2001) Supramolecular chemistry. Nankai University Press, Tianjin, pp 453–455Google Scholar
  23. 23.
    Huang WW, Lin H, Cai ZS, Lin HK (2010) Talanta 81:967–971PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Weiwei Huang
    • 1
  • Zhongyue Yang
    • 2
  • Hai Lin
    • 3
  • Huakuan Lin
    • 2
  1. 1.Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Chemistry CollegeNankai UniversityTianjinPeople’s Republic of China
  2. 2.Department of ChemistryNankai UniversityTianjinPeople’s Republic of China
  3. 3.Key Laboratory of Functional Polymer Materials of Ministry of EducationNankai UniversityTianjinPeople’s Republic of China

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