Abstract
The binding properties of pyrenyl-appended calix[4]arenes 2–4 towards lanthanide and transition metal cations were investigated by spectrophotometric data processing, which indicated that 2 forms mononuclear species with all the cations studied. The extraction power decreased toward ligands 2–3 except Co2+, then increased for ligand 4, which reflect the better ability of ligands 2 and 4 to complex and extract at the interface. Derivative 3 formed mono and binuclear species simultaneously with the trivalent cations from La3+ to Er3+ but only M2L species with Yb3+. In the case of 4, only M3L was detected for Yb3+ and only ML for La3+, with the complexation of the other cations tending to form mono-, bi- and tri-nuclear species.
Similar content being viewed by others
References
Kumar, R., Sharma, A., Singh, H., Suating, P., Kim, H.S., Sunwoo, K., Shim, I., Gibb, B.C., Kim, J.S.: Revisiting fluorescent calixarenes: from molecular sensors to smart materials. Chem. Rev. 119(16), 9657–9721 (2019)
Iuliano, V., Talotta, C., Gaeta, C., Soriente, A., De Rosa, M., Geremia, S., Hickey, N., Mennucci, B., Neri, P.: Negative solvatochromism in a N-linked p-pyridiniumcalix[4]arene derivative. Org. Lett. 21(8), 2704–2707 (2019)
Kumar, S., Kaur, J., Verma, A., Mukesh Kumar, A., Dominic, S.: Influence of polyether chain on the non-covalent interactions and stability of the conformers of calix[4]crown ethers. J. Incl. Phenom. Macrocycl. Chem. 91(1–2), 81–93 (2018)
Ovsyannikov, A., Solovieva, S., Antipin, I., Ferlay, S.: Coordination polymers based on calixarene derivatives: structures and properties. Coord. Chem. Rev. 352, 151–186 (2017)
Lou, X.Y., Song, N., Yang, Y.W.: Fluorescence resonance energy transfer systems in supramolecular macrocyclic chemistry. Molecules 22(10), 1640 (2017)
Baldini, L., Casnati, A., Sansone, F.: Comprehensive supramolecular chemistry II. In: Baldini, L. (ed.) Biomacromolecule Recognition by Calixarene Macrocycles, vol. 4, pp. 371–408. Elsevier, New York (2017)
Yoshida, K., Fujii, S., Takahashi, R., Matsumoto, S., Sakurai, K.: Self-assembly of calix[4]arene-based amphiphiles bearing polyethylene glycols: another example of “Platonic Micelles”. Langmuir 33(36), 9122–9128 (2017)
Redshaw, C.: Metallocalixarene catalysts: α-olefin polymerization and ROP of cyclic esters. Dalton Trans. 45(22), 9018–9030 (2016)
Gangemi, C.M.A., Pappalardo, A., Sfrazzetto, G.T.: Assembling of supramolecular capsules with resorcin[4]arene and calix[n]arene building blocks. Curr. Org. Chem. 19(23), 2281–2308 (2015)
Rodik, R.V., Klymchenko, A.S., Mely, Y., Kalchenko, V.I.: Calixarenes and related macrocycles as gene delivery vehicles. J. Incl. Phenom. Macrocycl. Chem. 80(3–4), 189–200 (2014)
Nimse, S.B., Kim, T.: Biological applications of functionalized calixarenes. Chem. Soc. Rev. 42(1), 366–386 (2013)
Mokhtari, B., Pourabdollah, K.: Application of calixarenes in development of sensors. Asian J. Chem. 25(1), 1–12 (2013)
Yang, Y., Zhao, Q., Feng, W., Li, F.: Luminescent chemodosimeters for bioimaging. Chem. Rev. 113(1), 192–270 (2013)
Asfari, Z., Böhmer, V., Harrowfield, J.M., Vicens, J. (eds.): Calixarenes 2001. Kluwer Academic, Dordercht (2001)
Thuéry, P., Nierlich, M., Lamare, É., Dozol, J.-F., Asfari, Z., Vicens, J.: Bis(crown ether) and azobenzocrown derivatives of calix[4]arene. A review of structural information from crystallographic and modelling studies. J. Incl. Phenom. Macrocycl. Chem. 36(4), 375–408 (2000)
Oueslati, I.: Calix(aza)crowns: synthesis, recognition, and coordination. A mini review. Tetrahedron 63(44), 10840–10851 (2007)
Pulpoka, B., Ruangpomvisuti, V., Asfari, Z., Vicens, J.: In: Takemura, H. (ed.) Cyclophane Chemistry for the 21st century, Chapter 3. Research Signpost, Kerala (2002)
Li, J.-S., Chen, Y.-Y., Lu, X.-R.: Syntheses of novel tripodal calix[n]cryptands (n = 4, 6) and their extraction abilities toward cations. Eur. J. Org. Chem. 2000(3), 485–490 (2000)
Ballester, P.: Anion binding in covalent and self-assembled molecular capsules. Chem. Soc. Rev. 39(10), 3810 (2010)
Zeng, X., Bornholdt, C., Over, D., Reinaud, O.: Synthesis of “Two-Story” calix[6]aza-cryptands. Org. Lett. 13(20), 5660–5663 (2011)
Reinhoudt, D.N., Dijkstra, P.J., Veld, P.J.A., Bugge, K.E., Harkema, S., Ungaro, R., Ghidini, E.: Kinetically stable complexes of alkali cations with rigidified calix[4]arenes. X-ray structure of calixspherand sodium picrate complex. J. Am. Chem. Soc. 109(15), 4761–4762 (1987)
Vicens, J., Asfari, Z., Harrowfield, J.M. (eds.): Calixarenes 50th Anniversary: Commemorative Issue. Springer, Dordrecht (1994)
Agbaria, K., Biali, S.E., Böhmer, V., Brenn, J., Cohen, S., Frings, M., Grynszpan, F., Harrowfield, J.M., Sobolev, A.N., Thondorf, I.: Stereochemistry of a spherand-type calixarene. J. Org. Chem. 66(9), 2900–2906 (2001)
Neri, P., Sessler, J.L., Wang, M.-X.: Calixarenes and Beyond. Springer, Cham (2016)
Mellah, B., Lee, Y.H., Kim, D.I., Cho, J.H., Kim, Y.: Synthesis of first-generation calix-dendrimer from 1,3,5-tris(aminomethyl)-2,4,6-trimethylbenzene and p-tert-butylcalix[4]arene monomethyl ester. J. Incl. Phenom. Macrocycl. Chem. 82(1–2), 279–282 (2015)
Gutsche, C.D.: Calixarenes: An Introduction. RSC Publishing, Cambridge (2008)
Cheriaa, N., Abidi, R., Vicens, J.: Hyperbranched molecules based on calixarenes. Tetrahedron Lett. 45(41), 7795–7799 (2004)
Othman, A.B., Lee, J.W., Huh, Y.D., Abidi, R., Kim, J.S., Vicens, J.: A novel pyrenyl-appended tricalix[4]arene for fluorescence-sensing of Al(III). Tetrahedron 63(44), 10793–10800 (2007)
Lhoták, P.: Chemistry of thiacalixarenes. Eur. J. Org. Chem. 2004(8), 1675–1692 (2004)
Morohashi, N., Narumi, F., Iki, N., Hattori, T., Miyano, S.: Thiacalixarenes. Chem Rev. 106(12), 5291–5316 (2006)
Kumar, R., Lee, Y.O., Bhalla, V., Kumar, M., Kim, J.S.: Recent developments of thiacalixarene based molecular motifs. Chem. Soc. Rev. 43(13), 4824 (2014)
Wang, J., Gutsche, C.D.: Tricalixarenes and pentacalixarenes: synthesis and complexation studies. J. Org. Chem. 67(13), 4423–4429 (2002)
Štastný, V., Stibor, I., Dvořáková, H., Lhoták, P.: Synthesis of (thia)calix[4]arene oligomers: towards calixarene-based dendrimers. Tetrahedron 60(15), 3383–3391 (2004)
Baklouti, L., Cheriaa, N., Maouhachi, M., Abidi, R., Kim, J.S., Kim, Y., Vicens, J.: Calixarene-based dendrimers. A timely review. J. Incl. Phenom. Macrocycl. Chem. 54(1–2), 1–7 (2006)
Cheriaa, N., Mahouachi, M., Othman, A.B., Baklouti, L., Kim, Y., Abidi, R., Vicens, J.: A new approach to dendrimers made from p-tert-butyl calix[4]arenes. Supramol. Chem. 18(3), 265–271 (2006)
Casnati, A., Pochini, A., Ungaro, R., Ugozzoli, F., Arnaud, F., Fanni, S., Schwing, M.-J., Egberink, R.J.M., Jong, F., Reinhoudt, D.N.: Synthesis, complexation, and membrane transport studies of 1,3-alternate calix[4]arene-crown-6 conformers: a new class of cesium selective ionophores. J. Am. Chem. Soc. 117(10), 2767–2777 (1995)
Frensdorff, H.K.: Salt complexes of cyclic polyethers. Distribution equilibriums. J. Am. Chem. Soc. 93(19), 4684–4688 (1971)
Noamane, M.H., Othmen, A.B., Al-Ayed, A.S., Kim, Y., Hayami, S., Hamdi, A.: 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(3–4), 249–256 (2019)
Pfeil, A., Lehn, J.-M.: Helicate self-organisation: positive cooperativity in the self-assembly of double-helical metal complexes. J. Chem. Soc. Chem. Commun. (1992). https://doi.org/10.1039/C39920000838
Sillén, L.G., Warnquist, B.: High speed computers as a supplement to graphical methods. Ark. Kemi. 31, 377 (1968)
Leggett, D.J.: The determination of formation constants. In: Leggett, D.J. (ed.) Computational Methods for the Determination of Formation Constants. Plenum Press, New York (1985)
Pearson, R.G.: Hard and Soft Acids and Bases - The Evolution of a Chemical Concept. Coord. Chem. Rev. 100, 403–425 (1990)
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Othman, A.B., Mellah, B., Abidi, R. et al. Complexing properties of pyrenyl-appended calix[4]arenes towards lanthanides and transition metal cations. J Incl Phenom Macrocycl Chem 97, 187–194 (2020). https://doi.org/10.1007/s10847-020-00993-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-020-00993-0