Skip to main content
Log in

Synthesis and anion recognition of neutral receptors based on multiamide calix[4]arene

  • Published:
Science in China Series B: Chemistry Aims and scope Submit manuscript

Abstract

Two multiamide calix[4]arenes (5, 6) were synthesized and characterized by NMR, MS and elemental analysis. The binding properties of receptors with some anions (π-O2NPhOPO 2−3 , π-O2NPhO, H2PO 4 , Ac, Cl, Br and I) were studied by UV-Vis spectra. The results indicate that the tetraamide calix[4]arenes (5, 6) have a good selectivity to the anions containing aromatic ring (π-O2NPhOPO3 2−, π-O2NPhO). The 1 : 1 complexes between host and guest were formed through multiple hydrogen bonding and π-π interactions. The hosts 5 and 6 also show a definite binding ability for the anions (H2PO 4 , Ac, Cl) that have no ultraviolet absorption, which provides a simple method of spectrum detection for these anions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. Buhlmann, P., Pretsch, E., Bakker, E., Carrier-based ion-selective electrodes and bulk optodes, 2. Innophores for potentiometric and optical sensors, Chem. Rev., 1998, 98(4): 1593–1687.

    Article  Google Scholar 

  3. Krai, 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, 1995, 51(2): 539–554.

    Article  Google Scholar 

  4. Kavauieratos, K., Carbtree, R. H., Catalysis of aldehyde imination by hydrogen bonding with a simple organic disulfonamide receptor, Chem. Commun., 1999, (20): 2109–2110.

  5. Hubner, G. M., Glaser, J., Sell, C. et al., High-yielding rotaxane synthesis with an anion template, Angew. Chem. Int. Ed. Engl., 1999, 38(3): 383–386.

    Article  CAS  Google Scholar 

  6. Beer, P. D., Drew, M. G. B., Gradwell, K., Synthesis and anion coordination chemistry of new calix[4]arene pyridinium receptors, J. Chem. Soc. Perkin. Trans. 2, 2000, 3: 511–519.

    Article  Google Scholar 

  7. Chrisstoffels, L. A. J., Jong, F., Reinhoudt, D. N. et al., Facilitated transport of hydrophilic salts by mixtures of anion and cation carriers and by ditopoc carreiers, J. Am. Chem. Soc., 1999, 121: 10142–10151.

    Article  CAS  Google Scholar 

  8. Shioya, T., Nishizawa, S., Teramae, N., Anion recognition at the liquid-liquid interface, Sulfate transfer across the 1,2-dichloroethane-water interface facilitated by hydrogen-bonding ionophores, J. Am. Chem. Soc., 1998, 120(44): 11534–11535.

    Article  CAS  Google Scholar 

  9. Liao, J. H., Chen, C. T., Fang, J. M., A novel phosphate chemosensor utilizing anion-induced fluorescence change, Org. Lett., 2002, 4(4): 561–564.

    Article  CAS  Google Scholar 

  10. Tuntulani, T., Tongraung, P., Chantarasiri, I. N., Calix[4]arenes containing urea and crown/urea moieties: effects of the crown ether unit and Na+ towards anion binding ability, Tetrahedron Lett., 2003, 44:29–32.

    Article  Google Scholar 

  11. Collins, E. M., Mckervey, M. A., Madigan, E. et al., Chemically modified calix [4] arenes, Regioselective synthesis of l,3-(distal) derivatives and related compounds, X-ray crystal structure of diphenol-dinitrile, J. Chem. Soc. Perkin. Trans. 1, 1991, 2: 3137–3142.

    Article  Google Scholar 

  12. Szumna, A., Jurczak, J., Anew macrocyclic polylactam-type neutral receptor for anions-structural aspects of anion recognition, Eur. J. Org. Chem., 2001: 4031–4039.

  13. Krapcho, A. P., Kuell, C. S., Mono-protected diamines: N-tert-butoxycarbonyl-α,ω-alkanediamines from α,ω-alkanediamines, Syn. Commun., 1990, 20(16): 2559–2564.

    Article  CAS  Google Scholar 

  14. Beer, P. D., Timoshenko, V., Maestri, M. et al., Anion recognition and luminescent sensing by new ruthenium (II) and rhenium (I) bipyridyl calix[4]diquinone receptors, Chem. Commun., 1999, 17: 1755–1756.

    Article  Google Scholar 

  15. Valeur, B., Pouget, J., Bourson, J., Tuning of photoinduced energy transfer in a bichromophoric cournarin supermolecule by cation binding, J. Phys. Chem., 1992, 96(16): 6545–6549.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yongbing He.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, S., Wang, F., Wei, L. et al. Synthesis and anion recognition of neutral receptors based on multiamide calix[4]arene. Sc. China Ser. B-Chem. 47, 145–151 (2004). https://doi.org/10.1360/03yb0124

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1360/03yb0124

Keywords

Navigation