Skip to main content
Log in

Interaction of 2-furanylmethyl- and 2-thienylmethyl-amide derivatives of 1,3-di(carboxymethyl)calix[4]arene with metal salts

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

The synthesis and metal-ion complexation properties of two new derivatives of 1,3-di(carboxymethyl)-p-tert-butylcalix[4]arene, bis(2-thienylmethylamide) 3 and bis(furanylmethylamide) 4, have been studied using UV/Vis spectrophotometry and, in some cases, 1H-NMR spectroscopy. The cations examined are alkali metals (Li+, Na+, K+, Rb+ and Cs+), alkaline earth metals (Mg2+, Ca2+, Sr2+ and Ba2+), heavy metals (Ag+, Cd2+, Hg2+ and Pb2+), and lanthanides (La3+, Nd3+, Eu3+, Gd3+ and Yb3+).

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.

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Gutsche, C.D.: Calixarenes. In: Stoddart, J.F., Gale, P. (eds.) Monographs in Supramolecular Chemistry, vol. 1. Royal Society of Chemistry, Cambridge (1989)

    Google Scholar 

  2. Böhmer, V., Vicens, J.: Topics in Inclusion Phenomena, Calixarenes a Verstaile Class of Macrocyclic Compounds. Kluwer Academic Publishers, Cham (1990)

    Google Scholar 

  3. Mokhtari, B., Pourabdollah, K., Dalali, N.: Analytical applications of calixarenes from 2005 up-to-date. J. Incl. Phenom. Macrocycl. Chem. 69, 1–55 (2011)

    Article  CAS  Google Scholar 

  4. Creaven, B.S., Donlon, D.F., McGinley, J.: Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications. Coord. Chem. Rev. 253, 893–962 (2009)

    Article  CAS  Google Scholar 

  5. Noamane, M.H., Ferlay, S., Abidi, R., Kyritsakas, N., Hosseini, M.W.: Formation of binuclear neutral Copper(II) complexes based on p-tert-butyl- calix[4]arene and thiacalix[4]arene in 1,3-A conformation bearing four catechols at their lower rim. Inorg. Chim. Acta 468, 260–269 (2017)

    Article  CAS  Google Scholar 

  6. Noamane, M.H., Ferlay, S., Abidi, R., Kyritsakas, N., Hosseini, M.W.: Synthesis of para- and meta-imino- or -amino-methyl pyridyl-appended p-tert-butyl-calix[4]arene or p-tert-butyl-thiacalix[4]arene in 1,3-alternate conformation. New J. Chem. 41, 6334–6339 (2017)

    Article  CAS  Google Scholar 

  7. Ovsyannikov, A.S., Noamane, M.H., Abidi, R., Ferlay, S., Solovieva, S.E., Antipin, I.S., Konovalov, A.I., Kyritsakas, N., Hosseini, M.W.: Molecular tectonics: dimensionality and geometry control of silver coordination networks based on pyrazolyl appended thiacalixarenes. CrystEngComm 18, 691–703 (2016)

    Article  CAS  Google Scholar 

  8. Matthews, S.E., Beer, P.D.: Calixarene-based anion receptors. Supramol. Chem. 17, 411–435 (2005)

    Article  CAS  Google Scholar 

  9. Kroupa, J., Stibor, I., Pojarová, M., Tkadlecová, M., Lhoták, P.: Anion receptors based on ureido-substituted thiacalix[4]arenes and calix[4]arenes. Tetrahedron 64, 10075–10079 (2008)

    Article  CAS  Google Scholar 

  10. Cuřínová, P., Pojarová, M., Budka, J., Lang, K., Stibor, I., Lhoták, P.: Binding of neutral molecules by p-nitrophenylureido substituted calix[4]arenes. Tetrahedron 66, 8047–8050 (2010)

    Article  CAS  Google Scholar 

  11. Smirnov, S., Sidorov, V., Pinkhassik, V., Havlicek, J., Stibor, I.: Complexes of p-t-butylcalix[4]arene derivatives with neutral molecules: structures and stabilities. Supramol. Chem. 8, 187–196 (1997)

    Article  CAS  Google Scholar 

  12. Arena, G., Contino, A., Longo, E., Spoto, G., Arduini, A., Pochini, A., Secchi, A., Massera, C., Ugozzolli, F.: An integrated approach to the study of the recognition of guests containing CH3 and CH2 acidic groups by differently rigidified cone p-tert-butylcalix[4]arene derivatives. New J. Chem. 28, 56–61 (2004)

    Article  CAS  Google Scholar 

  13. Sviben, I., Galić, N., Tomišić, V., Frkanec, L.: Extraction and complexation of alkali and alkaline earth metal cations by lower-rim calix[4]arene diethylene glycol amide derivatives. New J. Chem. 39, 6099–6107 (2015)

    Article  CAS  Google Scholar 

  14. Hamdi, A., Noomen, M.H., Abidi, R., Woo, A.R., Cho, J.H., Kim, Y.: Synthesis and cation complexation of calix[4]azacrowns and a spirobiscalix[4]azacrown. J. Incl. Phenom. Macrocycl. Chem. 71, 287–291 (2011)

    Article  CAS  Google Scholar 

  15. Driscolla, C.R., Skeltonb, B.W., Massia, M., Ogden, M.I.: Structural characterisation and photophysical properties of lanthanoid complexes of a tetra-amide functionalised calix[4]arene. Supramol. Chem. 28, 567–574 (2016)

    Article  CAS  Google Scholar 

  16. De Solis, S., Elisei, F., Gunnlaugsson, T.: Lower rim amide (1,3) functionalised calix[4]arene amido-thiourea derivatives as dimetallic Zn(II) coordination complexes for anion recognition/sensing. Supramol. Chem. 27, 697–705 (2015)

    Article  CAS  Google Scholar 

  17. Marcos, P.M., Fonseca, J.D., Proença, C.S., Ascenso, J.R., Bernardino, R.J., Kulesza, J.: Bochenska M (2016) Experimental and computational studies of the binding properties of lower rim tetra- and di-substituted calix[4]arene amide derivatives with metal ions. Supramol. Chem. 28, 367–376 (2016)

    Article  CAS  Google Scholar 

  18. Gutsche, C.D., Iqbal, M.: p-tert-Butylcalix[4]arene. Org. Synth. 68, 234–236 (1990)

    Article  CAS  Google Scholar 

  19. Unob, F., Asfari, Z., Vicens, J.: An anthracene-based fluorescent sensor for transition metal ions derived from calix[4]arene. Tetrahedron Lett. 39, 2951–2954 (1998)

    Article  CAS  Google Scholar 

  20. Hamdi, A., Lee, Y.H., Kim, Y., Kusumahastuti, D.K.A., Ohto, K., Abidi, R., Vicens, J.: A spirobiscalix[4]azacrown: synthesis and complexing properties. Tetrahedron Lett. 50, 540–543 (2009)

    Article  CAS  Google Scholar 

  21. Collins, E.M., McKervey, M.A., Harris, S.J.: Molecular receptors with the calix[4]arene substructure. Synthesis of derivatives with mixed ligating functional groups. J. Chem. Soc. Perkin Trans. 1, 372–374 (1989)

    Article  Google Scholar 

  22. van Loon, J.-D., Arduini, A., Verboom, W., Ungaro, R., van Hummel, G.J., Harkema, S., Reinhoudt, D.N.: Selective functionalization of calix[4]arenes at the upper rim. Tetrahedron Lett. 30, 2681–2684 (1989)

    Article  Google Scholar 

  23. van Loon, J.-D., Arduini, A., Coppi, L., Verboom, W., Pochini, A., Ungaro, R., Harkema, S., Reinhoudt, D.N.: Selective functionalization of calix[4]arenes at the upper rim. J. Org. Chem. 55, 5639–5646 (1990)

    Article  Google Scholar 

  24. Collins, E.M., McKervey, M.A., Madigan, E., Moran, M.B., Owens, M., Ferguson, G., Harris, S.J.: Chemically modified calix[4]arenes. Regioselective synthesis of 1,3-(distal) derivatives and related compounds. X-Ray crystal structure of a diphenol-dinitrile. J. Chem. Soc. Perkin Trans. 1, 3137–3142 (1991)

    Article  Google Scholar 

  25. Böhmer, V., Wolff, A., Vogt, W.: A new route to chiral calix[4]arenes via 1,3-derivatization. J. Chem. Soc., Chem. Commun. 14, 968–970 (1990)

    Article  Google Scholar 

  26. Liu, Y., Chen, Y., Li, L., Huang, G., You, C.-C., Zhang, H.-Y., Wada, T., Inoue, Y.: Cooperative multiple recognition by novel calix[4]arene-tethered β-cyclodextrin and calix[4]arene-bridged bis(β-cyclodextrin). J. Org. Chem. 66, 7209–7215 (2001)

    Article  CAS  PubMed  Google Scholar 

  27. Marquis, D., Henze, B., Bouas-Laurent, H., Desvergne, J.-P.: Synthesis and cation completing properties of a new type of photoactive coronands towards photocontrol of Na+ complexation. Tetrahedron Lett. 39, 35–38 (1998)

    Article  CAS  Google Scholar 

  28. Hamdi, A., Abidi, R., Asfari, Z., Vicens, J.: Synthesis and complexing properties of four new tetraamido-type p-tert-butyl calix[4]arenes presenting two proximal binding subunits. J. Incl. Phenom. Macrocycl. Chem. 45, 97–105 (2003)

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by Laboratory of Applied Chemistry and Natural Substances Resources and Environment (LACReSNE) Bizerte – Tunisia and Department of Chemistry Sciences and Arts College in the Al-Rass province Al-Qassim University – KSA. The authors gratefully acknowledge Qassim University, represented by the Deanship of Scientific Research.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Abdelwaheb Hamdi.

Additional information

Dedicated to Prof. Karsten Gloe on the occasion of his 70th birthday.

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Noamane, M.H., Ben Othmen, A., Al-Ayed, A.S. et al. Interaction of 2-furanylmethyl- and 2-thienylmethyl-amide derivatives of 1,3-di(carboxymethyl)calix[4]arene with metal salts. J Incl Phenom Macrocycl Chem 94, 249–256 (2019). https://doi.org/10.1007/s10847-019-00908-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-019-00908-8

Keywords

Navigation