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A novel switch-on fluorescent receptor for bromide based on an amide group

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Abstract

A novel switch-on fluorescent receptor for bromide was demonstrated and its binding ability toward anions was investigated by fluorescence spectroscopes and 1H NMR titration experiments. Addition of Br to a DMSO solution of N,N-di-p-bromophenyl-1,10-phenanthroline-2,9-diamide (1) resulted in an enhancement in fluorescence intensity at 377 nm and 396 nm. Two signaling transduction mechanisms were exploited to rationalize quenching and enhancement of the fluorescence emission: inhibition of a photo-induced electronic transfer mechanism (PET) and anion-induced increase of the rigidity of the host molecule.

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References

  1. Kruppa, M., König, B.: Reversible coordinative bonds in molecular recognition. Chem. Rev. 106, 3520–3560 (2006)

    Article  CAS  Google Scholar 

  2. Shao, J., Lin, H., Yu, M., Cai, Z.Sh., Lin, H.K.: Study on acetate ion recognition and sensing in aqueous media using a novel and simple colorimetric sensor and its analytical application. Talanta. 75, 551–555 (2008)

    Article  CAS  Google Scholar 

  3. Shao, J., Lin, H., Shang, X.F., Chen, H.M., Lin, H.K.: A novel neutral receptor for selective recognition of H2PO 4 . J. Incl. Phenom. Macrocycl. Chem. 59, 371–375 (2007)

    Article  CAS  Google Scholar 

  4. Shao, J., Lin, H., Lin, H.K.: A simple and efficient colorimetric anion receptor for H2PO 4 . Spectrochim. Acta Part A. doi: 10.1016/j.saa.2007.08.018(in press)

  5. Grases, F., March, J.G.: Determination of phosphate based on inhibition of crystal growth of calcite. Anal. Chim. Acta 229, 249–254 (1990)

    Article  CAS  Google Scholar 

  6. Maeda, H., Ito, Y.: BF2 complex of fluorinated dipyrrolyldiketone: a new class of efficient receptor for acetate anions. Inorg. Chem. 46, 8205–8210 (2006)

    Article  CAS  Google Scholar 

  7. Beer, P.D., Szemes, F., Balzani, V., Salà, C.M., Drew, M.G.B., Dent, S.W., Maestri, M.: Anion selective recognition and sensing by novel macrocyclic transition metal receptor systems. 1H NMR, electrochemical, and photophysical investigations. J. Am. Chem. Soc. 119, 11864–1175 (1997)

    Article  CAS  Google Scholar 

  8. Amendola, V., Bastianello, E., Fabbrizzi, L., Mangano, C., Pallavicini, P., Perotti, A., Lanfredi, A.M., Ugozzoli, F.: Halide-ion encapsulation by a flexible dicopper(ii) bis-tren cryptate. Angew. Chem. Int. Ed. 39, 2917–3920 (2000)

    Article  CAS  Google Scholar 

  9. 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 

  10. Liu, W.X., Jiang, Y.B.: N-Amidothiourea based PET chemosensors for anions. Org. Biomol. Chem. 5, 1771–1775 (2007)

    Article  CAS  Google Scholar 

  11. 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 

  12. Kang, J.M., Kim, H.S., Jang, D.O.: Fluorescent anion chemosensors using 2-aminobenzimidazole receptors. Tetrahedron Lett. 46, 6079–6082 (2005)

    Article  CAS  Google Scholar 

  13. Han, F., Bao, Y.H., Yang, Zh.G., Fyles, T.M., Zhao, J.Zh., Peng, X.J., Fan, J.L., Wu, Y.K., Sun, Sh.G.: 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 

  14. Gunnlaugsson, T., Ali, H.D.P., Glynn, M., Kruger, P.E., Hussey, G.M., Pfeffer, F.M., Dos Santos, C.M.G., Tierney, J.: Fluorescent photoinduced electron transfer (PET) sensors for anions: from design to potential application. J. Fluoresc. 15, 287–299 (2005)

    Article  CAS  Google Scholar 

  15. Martínez-Máñez, R., Sancenón, F.: Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev. 103, 4419–4476 (2003)

    Article  CAS  Google Scholar 

  16. Gunnlaugsson, T., Kruger, P.E., Lee, T.C., Parkesh, R., Pfeffer, F.M., Hussey, G.M.: Dual responsive chemosensors for anions: the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule. Tetrahedron Lett. 44, 6575–6578 (2003)

    Article  CAS  Google Scholar 

  17. Lin, Zh.H., Zhao, Y.G., Duan, Ch.Y., Zhang, B.G., Bai, Zh.P.: A highly selective chromo- and fluorogenic dual responding fluoride sensor: naked-eye detection of F ion in natural water via a test paper. Dalton Trans. 3678–3684 (2006) and references therein

  18. Lee, D.H., Im, J.H., Lee, J.H., Hong, 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 

  19. Watanabe, S., Onogawa, O., Komatsu, Y., Yoshida, K.: Luminescent metalloreceptor with a neutral bis(acylaminoimidazoline) binding site: optical sensing of anionic and neural phosphodiesters. J. Am. Chem. Soc. 120, 229–230 (1998)

    Article  CAS  Google Scholar 

  20. Bourson, J., Pouget, J., Valeur, B.: Ion-responsive fluorescent compounds. 4. Effect of cation binding on the photophysical properties of a coumarin linked to monoaza- and diaza-crown ethers. J. Phys. Chem. 97, 4552–4556 (1993)

    Article  CAS  Google Scholar 

  21. Singh, N., Jang, D.O.: Benzimidazole-based tripodal receptor: highly selective fluorescent chemosensor for iodide in aqueous solution. Org. Lett. 9, 1991–1994 (2007)

    Article  CAS  Google Scholar 

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Acknowledgment

This project was supported by the National Natural Science Foundation of China (NO.20371028, NO.20671052).

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Correspondence to Hua-Kuan Lin.

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Shao, J., Qiao, YH., Lin, H. et al. A novel switch-on fluorescent receptor for bromide based on an amide group. J Incl Phenom Macrocycl Chem 62, 99–103 (2008). https://doi.org/10.1007/s10847-008-9443-3

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  • DOI: https://doi.org/10.1007/s10847-008-9443-3

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