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Anion recognition based on phenolic hydroxyl group in competitive media

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Abstract

Two novel artificial receptors, one containing phenolic hydroxyl group and diamide (1), the other only containing diamide (2), were designed and synthesized. The binding ability evaluated by UV–vis and fluorescence titration experiments in dry DMSO revealed that compound 1 could selectively recognize AcO−. In particular, the binding ability can also be detected in the DMSO/H2O solution by UV–vis. The interference experiment result showed that the binding ability was not influenced by the existence of other anions. In contrast, there were no detectable interaction between receptor 2 and anions. The further insights to the nature of interaction between receptor 1 and AcO− were investigated by 1H NMR titration experiments and theoretical investigation, which demonstrated receptor 1 complexed AcO− through the synergistic hydrogen bonding interaction of OH and NH.

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References

  1. Sjevcjuk, S.V., Lynch, V.M., Sessler, J.L.: A new terpyrrolic analogue of dipyrrolylquinoxalines: an efficient optical-based sensor for anions in organic media. Tetrahedron 60, 11283–11291 (2004)

    Article  Google Scholar 

  2. Gale, P.A.: Anion coordination and anion-directed assembly: highlights from 1997 and 1998. Coord. Chem. Rev. 199, 181–233 (2000)

    Article  CAS  Google Scholar 

  3. Beer, P.D., Gale, P.A.: Anion recognition and sensing: the state of the art and future perspectives. Angew. Chem. Int. Ed. 40, 486–516 (2001)

    Article  CAS  Google Scholar 

  4. Gale, P.A.: Anion receptor chemistry: highlights from 1999. Coord. Chem. Rev. 213, 79–128 (2001)

    Article  CAS  Google Scholar 

  5. Sessler, J.L., Davis, J.M.: Sapphyrins: versatile anion binding agents. Acc. Chem. Rev. 34, 989–997 (2001)

    Article  CAS  Google Scholar 

  6. Sancenon, F., Martinez-Manez, R., Miranda, M.A., Segui, M.J., Soto, J.J.: Towards the development of colorimetric probes to discriminate between isomeric dicarboxylates. Angew. Chem. Int. Ed. 42, 647–650 (2003)

    Article  CAS  Google Scholar 

  7. Bondy, C.R., Loeb, S.J.: Amide based receptors for anions. Coord. Chem. Rev. 240, 77–99 (2003)

    Article  CAS  Google Scholar 

  8. Gale, P.A.: Anion and ion-pair receptor chemistry: highlights from 2000 and 2001. Coord.Coord. Chem. Rev. 240, 191–221 (2003)

    Article  CAS  Google Scholar 

  9. Valeria, A., Luigi, F., Lorenzo, M.: Anion recognition by hydrogen bonding: urea-based receptors. Chem. Soc. Rev. 39, 3889–3915 (2010)

    Article  Google Scholar 

  10. Gabriella, C., Pierangelo, M., Tullio, P., Giuseppe, R., Maurizio, S., Giancarlo, T.: Halogen bonding: a general route in anion recognition and coordination. Chem. Soc. Rev. 39, 3772–3783 (2010)

    Article  Google Scholar 

  11. Buhlmann, P., Pretsch, E., Bakker, E.: Carrier-based ion-selective electrodes and bulk optodes. 2. Ionophores for potentiometric and optical sensors. Chem. Rev. 98, 1593–1688 (1998)

    Article  Google Scholar 

  12. Hassan, S.S.M., Attawiya, A.M.Y.: A novel uranyl membrane sensor with potentiometric anionic response. Talanta. 70, 883–889 (2006)

    Article  CAS  Google Scholar 

  13. Kral, V., Sessler, J.L.: Molecular recognition via base-pairing and phosphate chelation. Ditopic and tritopic sapphyrin-based receptors for the recognition and transport of nucleotide monophosphates. Tetrahedron 51, 539–554 (1995)

    Article  CAS  Google Scholar 

  14. Jesús Seguí, M., Lizondo-Sabater, J., Benito, A.: A new ion-selective electrode for anionic surfactants. Talanta 71, 333–338 (2007)

    Article  Google Scholar 

  15. Hossain, M.A., Liljeren, J.A., Powell, D., Jame, K.B.: Anion binding with a tripodal amine. Inorg. Chem. 43, 3751–3755 (2004)

    Article  CAS  Google Scholar 

  16. Shao, J., Lin, H., Shang, X.F., Chen, H.M., Lin, H.K.: A novel neutral receptor for selective recognition of H2PO4 −. J. Inclusion Phenom. Macrocyclic Chem 59, 371–375 (2007)

    Article  CAS  Google Scholar 

  17. Shin-ichi, K.: Effect of hydroxyl groups in receptors bearing disulfonamide on anion recognition in acetonitrile-d3. Tetrahedron Lett. 43, 7059–7061 (2002)

    Article  Google Scholar 

  18. Shang, X.F., Lin, H., Cai, Z.S., Lin, H.K.: Effects of the receptors bearing phenol group and copper(II) on the anion recognition and their analytical application. Talanta. 73, 296–303 (2007)

    Article  CAS  Google Scholar 

  19. Jose, D.A., Kar, P., Koley, D., Ganguly, B.: Phenol- and catechol-based ruthenium(II) polypyridyl complexes as colorimetric sensors for fluoride ions. Inorg.Chem. 46, 5576–5584 (2007)

    Article  CAS  Google Scholar 

  20. Davis, A.P., Perry, J.J., Wareham, R.S.: Anion recognition by alkyl cholates: neutral anionophores closely related to a natural product. Tetrahedron Lett. 39, 4569–4572 (1998)

    Article  CAS  Google Scholar 

  21. Zhang, X., Guo, L., Wu, F.Y., Jiang, Y.B.: Development of fluorescent sensing of anions under excited-state intermolecular proton transfer signaling mechanism. Org. Lett. 5, 2667–2670 (2003)

    Article  CAS  Google Scholar 

  22. Bao, X.P., Zhou, Y.H.: Synthesis and recognition properties of a class of simple colorimetric anion chemosensors containing OH and CONH groups. Sensors and Actuators B 147, 434–441 (2010)

    Article  Google Scholar 

  23. Bao, X.P., Yu, J.H., Zhou, Y.H.: Selective colorimetric sensing for F− by a cleft-shaped anion receptor containing amide and hydroxyl as recognition units. Sensors and Actuators B 140, 467–472 (2009)

    Article  Google Scholar 

  24. Gunnlaugsson, T., Davis, A.P., O’Brien, J.E., Glynn, M.: Fluorescent sensing of pyrophosphate and bis-carboxylates with charge neutral PET chemosensors. Org. Lett. 4, 2449–2452 (2002)

    Article  CAS  Google Scholar 

  25. Shao, J., Lin, H., Lin, H.K.: Rational design of a colorimetric and ratiometric fluorescent chemosensor based on intramolecular charge transfer (ICT). Talanta. 77, 273–277 (2008)

    Article  CAS  Google Scholar 

  26. Li, Y.P., Li, J.W., Lin, H., Shao, J., Cai, Z.S., Lin, H.K.: A novel colorimetric receptor responding AcO− anions based on an azo derivative in DMSO and DMSO/water solution. Journal of Luminescence 130, 466–472 (2010)

    Article  CAS  Google Scholar 

  27. Zhang, Y.H., Yin, Z.M., He, J.Q., Cheng, J.P.: Effective receptors for fluoride and acetate ions: synthesis and binding study of pyrrole- and cystine-based cyclopeptido-mimetics. Tetrahedron Lett. 48, 6039–6043 (2007)

    Article  CAS  Google Scholar 

  28. Maeda, H., Ito, Y.: BF2 complex of fluorinated dipyrrolyldiketone: a new class of efficient receptor for acetate anions. Inorg. Chem. 45, 8205–8210 (2006)

    Article  CAS  Google Scholar 

  29. Wu, F.Y., Li, Z., Wen, Z.C., Zhou, N., Zhao, Y.F., Jiang, Y.B.: A novel thiourea-based dual fluorescent anion receptor with a rigid hydrazine spacer. Organic letter 4, 3203–3205 (2002)

    Article  CAS  Google Scholar 

  30. Han, F., Bao, Y.H., Yang, Z.G., Fyles, T.M.: Simple bisthiocarbonohydrazones as sensitive, selective, colorimetric, and switch-on fluorescent chemosensors for fluoride anions. Chem. Eur. J. 13, 2880–2892 (2007)

    Article  CAS  Google Scholar 

  31. Liu, Y., Han, B.H., Zhang, H.Y.: Spectroscopic studies on molecular recognition of modified cyclodextrins. Curr. Org. Chem. 8, 35–46 (2004)

    Article  CAS  Google Scholar 

  32. Liu, Y., You, C.C., Zhang, H.Y.: Supramolecular Chemistry. Nankai University Publication, Tian Jin (2001)

    Google Scholar 

  33. Korendovych, I.V., Cho, M., Butler, P.L., Staples, R.J., Rybak-Akimova, E.V.: Anion binding to monotopic and ditopic macrocyclic amides. Org Lett 8, 3171–3174 (2006)

    Article  CAS  Google Scholar 

  34. Lee, D.H., Im, J.H., Lee, J.H., Honga, J.I.: A new fluorescent fluoride chemosensor based on conformational restriction of a biaryl fluorophore. Tetrahedron Lett. 43, 9637–9640 (2002)

    Article  CAS  Google Scholar 

  35. Frisch, M.J., Trucks, W., Schlegel, H.B., Scuseria, G.E.: Gaussian 03, Revision A. 1. Gaussian, Inc., Pittsburgh, PA (2003)

    Google Scholar 

  36. Shang, X.F., Xu, X.F., Lin, H., Shao, J., Lin, H.K.: Efficient fluoride-selective receptor: experiment and theory. J. Incl. Phenom. Macrocycl. Chem. 58, 275–281 (2007)

    Article  CAS  Google Scholar 

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Acknowledgment

This work was supported by the NSF of Henan Province (2010B150024) and Doctorial Science Fund of Henan Normal University and Xinxiang Medical University.

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Authors and Affiliations

  1. Henan Normal University, Xinxiang, Henan, 453003, China

    Xin-Juan Li

  2. Xinxiang Medical University, Xinxiang, Henan, 453003, China

    Xin-Juan Li, Xue-Fang Shang, Lei-Lei Liu, Nan-kai Xi & Jin-Lian Zhang

  3. Nankai University, Tianjin, 300071, China

    Xiu-Fang Xu

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  1. Xin-Juan Li
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  2. Xue-Fang Shang
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Correspondence to Xin-Juan Li or Xue-Fang Shang.

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Li, XJ., Shang, XF., Liu, LL. et al. Anion recognition based on phenolic hydroxyl group in competitive media. J Incl Phenom Macrocycl Chem 73, 185–192 (2012). https://doi.org/10.1007/s10847-011-0041-4

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  • DOI: https://doi.org/10.1007/s10847-011-0041-4

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