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.
Similar content being viewed by others
References
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.
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.
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.
Kavauieratos, K., Carbtree, R. H., Catalysis of aldehyde imination by hydrogen bonding with a simple organic disulfonamide receptor, Chem. Commun., 1999, (20): 2109–2110.
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.
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.
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.
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.
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.
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.
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.
Szumna, A., Jurczak, J., Anew macrocyclic polylactam-type neutral receptor for anions-structural aspects of anion recognition, Eur. J. Org. Chem., 2001: 4031–4039.
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.
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.
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.
Author information
Authors and Affiliations
Corresponding author
Rights 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
Received:
Issue Date:
DOI: https://doi.org/10.1360/03yb0124