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Allosteric bindings of thiacalix[4]arene-based receptors with 1,3-alternate conformation having two different side arms

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Abstract

A novel ditopic receptor possessing two complexation sites such as crown ether and 2-pyridylmethyl groups bearing 1,3-alternate conformation based on thiacalix[4]arene was prepared. The binding behaviors with Li+ and Ag+ have been examined by 1H NMR titration experiment. The exclusive formation of mononuclear complexes of 1,3-alternate-5 with Li+ and Ag+ was observed even though the formation of the heterogeneous dinuclear complexes was expected. The decomplexation of Li+ from the crown moiety of 1:1 complex 1,3-alternate-5⊃Li+ to form the Ag+⊂1,3-alternate-5 complex by addition of AgSO3CF3 clearly shows that pyridyl moiety works as an efficient switch-off of the recognition ability of the crown moiety. We have also developed the construction of hydrogen-bonding self-assembly heterodimeric systems based on bis(4-pyridyl) and dicarboxylic acid thiacalix[4]arene derivatives in 1,3-alternate conformation. Their supramolecular behaviors are studied by 1H NMR titration experiments with K+ and Ag+ ions. Although the values of the dimerization constants are relatively small, the stability of the dimers is strong enough to overcome only small conformational changes upon complex formation.

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References

  1. (a) Gutsche, C.D.: In: Stoddart, J. F. (ed.) Calixarenes revisited, Monographs in Supramolecular Chemistry, vol. 6. The Royal Society, Cambridge (1998); (b) Asfari, Z., Böhmer, V. Harrowfield, J., Vicens, J.: Calixarenes 2001. Kluwer Academic, Dordrecht (2001); (c) Vögtle, F.: Supramolecular Chemistry: An Introduction. J. Wiley, New York (1991).

  2. (a) Lhoták, P.: Chemistry of Thiacalixarenes. Eur. J. Org. Chem. 1675–1692 (2004); (b) Morohashi, N., Narumi, F., Iki, N., Hattori, T., Miyano, S.: Thiacalixarenes. Chem. Rev. 106, 5291–5316 (2006); (c) Kumagai, J., Hasegawa, M., Miyanari, S., Sugawa, Y., Sato, Y., Hori, T., Ueda, S., Kamiyama, H., Miyano, S.: Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a base. Tetrahedron Lett. 38, 3971–3972 (1997); (d) Iki, N., Kabuto, C., Fukushima, T., Kumagai, H., Takeya, H., Miyanari, S., Miyashi, T., Miyano, S.: Synthesis of p-tert-butylthiacalix[4]arene and its inclusion property. Tetrahedron 56, 1437–1443 (2000).

  3. Lehn, J.M.: Supramolecular Chemistry: Concepts and Perspectives. VCH, Weinheim, Germany (1995).

    Google Scholar 

  4. (a) Nabeshima, T., Saiki, T., Sumitomo, K.: Modulation of metal recognition by a novel calix[4]arene bearing two bipyridine units as a molecular gate. Org. Lett. 4, 3207–3209 (2002); (b) Nabeshima, T., Yoshihira, Y., Saiki, T., Akine, S., Horn, E.: Remarkably large positive and negative allosteric effects on ion recognition by the formation of a novel helical pseudocryptand. J. Am. Chem. Soc. 125, 28–29 (2003).

    Google Scholar 

  5. Hammes, G.G., Wu, C.W.: Kinetics of allosteric enzymes. Annu. Rev. Biophys. Bioeng. 3, 1–33 (1974).

    Article  CAS  Google Scholar 

  6. (a) Iwamoto, K., Shinkai, S.: Synthesis and ion selectivity of all conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]calix[4]arene. J. Org. Chem. 57, 7066–7073 (1992); (b) Ikeda, A., Shinkai, S.: On the origin of high ionophoricity of 1,3-alternate calix[4]arenes: pi-donor participation in complexation of cations and evidence for metal-tunneling through the calix[4]arene cavity. J. Am. Chem. Soc. 116, 3102–3110 (1994); (c) Koh, K.N., Araki, K., Shinkai, S., Asfari, Z., Vicens, J.: Cation binding properties of a novel 1,3-alternate calix[4]biscrown. Formation of 1:1 and 1:2 complexes and unique cation tunneling across a calix[4]arene cavity. Tetrahedron Lett. 36, 6095–6098 (1995).

    Google Scholar 

  7. (a) van Leeuwen, F.W.B., Beijleveld, H., Kooijiman, H., Spek, A.L., Verboom, W., Reinhoudt, D.N.: Synthesis and conformational evaluation of p-tert-butylthiacalix[4]arene-crowns. J. Org. Chem. 69, 3928–3936 (2004); (b) Lamare, V., Dozol, J.F., Thuéry, P., Nierlich, M., Asfari, Z., Vicens, J.: Experimental and theoretical study of the first thiacalixcrowns and their alkali metal ion complexes. J. Chem. Soc., Perkin Trans. 2, 1920–1926 (2001).

    Google Scholar 

  8. (a) Grün, A., Csokai, V., Parlagh, G., Bitter, I.: Synthesis and alkali cation extraction ability of 1,3-alt-thiacalix[4]bis(crown) ethers. Tetrahedron Lett. 43, 4153–4156 (2002); (b) Csokai, V., Grün, A., Parlagh, G., Bitter, I.: Synthesis and alkali cation extraction ability of 1,3-alt-thiacalix[4]mono(crown) ethers. Tetrahedron Lett. 43, 7627–7629 (2002).

    Google Scholar 

  9. (a) Kubo, Y., Maeda, S., Tokita, S., Kubo, M.: Colorimetric chiral recognition by a molecular sensor. Nature 382, 522–524 (1996); (b) Zheng, Q.Y., Chen, C.F., Huang, Z.T.: Synthesis of new chromogenic calix[4]crowns and molecular recognition of alkylamines. Tetrahedron 53, 10345–10356 (1997); (c) Arnaud-Neu, F., Caccamese, S., Fuangswasdi, S., Pappalardo, S., Parisi, M.F., Petringa, A., Principato, G.: Synthesis, optical resolution and complexation properties of inherently chiral monoalkylated p-tert-butyl-(1,2)-calix[4]crown ethers. J. Org. Chem. 62, 8041–8048 (1997).

    Google Scholar 

  10. (a) Ungaro, R., Casnati, A., Ugozzoli, F., Pochini, A., Dozol, J.-F., Hill, C., Pouquette, H.: 1,3-Dialkoxycalix[4]arenecrowns-6 in 1,3-alternate conformation: cesium-selective ligands that exploit cation–arene interactions. Angew. Chem., Int. Ed. Engl. 33, 1506–1509 (1994); (b) Lamare, V., Dozol, J.F., Fuangswasdi, S., Arnaud-Neu, F., Thuéry, P., Nierlich, M., Asfari, Z., Vicens, J.: A new calix[4]arene-bis(crown ether) derivative displaying an improved caesium over sodium selectivity: molecular dynamics and experimental investigation of alkali-metal ion complexation. J. Chem. Soc., Perkin Trans 2, 271–284 (1999).

    Google Scholar 

  11. (a) Thuéry, P., Nierlinch, M., Lamare, V., 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. Macrocyclic Chem. 36, 375–408 (2000); (b) Blanda, M.T., Farmer, D.F., Brpdbelt, J.S., Goolsby, B. J.: Synthesis and alkali metal ion binding properties of two rigid sterochemical isomers of calix[6]arene bis-crown-4. J. Am. Chem. Soc. 122, 1486–1491 (2000); (c) Izatt, R.M., Pawlak, K., Bradshaw, J.S., Bruening, R.L.: Thermodynamic and kinetic data for macrocycle interactions with cations and anions. Chem. Rev. 91, 1721–2085 (1991); (d) Arena, G.. Contino, A., Magri, A., Scioto, D., Spoto, G., Torrisi, A.: Strategies based on calixcrowns for the detection and removal of cesium ions from alkali-containing solutions. Ind. Eng. Chem. Res. 39, 3605–3610 (2000); (e) Luo, H., Dai, S., Bonnesen, P.V., Buchana, A.C., Holbrey, J.D., Bridges, N.J., Rogers, R.D.: Extraction of cesium ions from aqueous solutions using calix[4]arene-bis(tert-octylbenzo-crown-6) in ionic liquids. Anal. Chem. 76, 3078–3083 (2004); (f) Casnati, A., Della Ca’, N., Sansone, F., Ugozzoli, F., Ungaro, R.: Enlarging the size of calix[4]arene-crowns-6 to improve Cs+/K+ selectivity: a theoretical and experimental study. Tetrahedron 60, 7869–7876 (2004).

    Google Scholar 

  12. (a) Casnati, A., Pochini, A., Ignaro, R., Ugozzoli, F., Arnaud, F., Fanni, S., Schwing, M.-J., Egberink, R.J.M., de 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, 2767–2777 (1995); (b) Kim, J.S., Suh, I.H., Kim, J.K., Cho, M.H.: Selective sensing of caesium ions by novel calix[4]arene bis-(dibenzocrown) ethers in an aqueous environment. J. Chem. Soc., Perkin Trans. 1, 2307–2312 (1998); (c) Asfari, Z., Weiss, J., Papparlardo, S., Vicens, J.: Synthesis and properties of double-calix[4]arenes, doubly-crowned calix[4]arenes, and double-calix-crowns. Pure Appl. Chem. 65, 585–590 (1993); (d) Stephan, H., Gloe, K., Paulus, E.F., Saadioui, M., Böhmer, V.: Calix crowns derived from para-bridged calix[4]arenas. Org. Lett. 2, 839–841 (2000).

    Google Scholar 

  13. (a) Ferguson, G., Gallagher, J.F., Giunta, L., Neri, P., Pappalardo, S., Parisi, M.: Synthetic strategies to inherently chiral calix[4]arenes with mixed ligating functionalities at the lower rim. J. Org. Chem. 59, 42–53 (1994); (b) Pappalardo, S., Ferguson, G., Neri, P., Rocco, C.: Synthesis and complexation studies of regioisomers and conformational isomers of p-tert-butylcalix[4]arene bearing pyridine or pyridine N-oxide pendant groups at the lower rim. J. Org. Chem. 60, 4576–4584 (1995); (c) Pappalardo, S.: Self-filled partial cone pyridinocalix[4]arenes. New J. Chem. 465–472 (1996); (d) De Danil, N., Angela, F., Piro, O.E., Pulcha, S., Lupe, E., Aguilar, C., Adolfo, F., Al-Rawi, N., Catellano, E.E., Sueros, V., Felix, J.: Solution thermodynamics of geometrical isomers of pyridino calix(4)arenes and their interaction with the silver cation. The X-ray structure of a 1:1 complex of silver perchlorate and acetonitrile with 5,11,17,23-tetra-tert-butyl-[25,26,27,28-tetrakis(2-pyridylmethyl)oxy]calix[4]arene. J. Chem. Soc. Faraday Trans. 94, 3097–3104 (1998); (e) Shinkai, S., Fujimoto, K., Otsuka, T., Ammon, H.-L.: Syntheses and ion selectivity of conformational isomers derived from calix[4]arene. J. Org. Chem. 57, 1516–1523 (1992).

    Google Scholar 

  14. (a) Yamato, T., Haraguchi, M., Iwasa, T., Tsuzuki, H.: Synthesis and inclusion propeties of tetrakis[(2-pyridylmethyl)oxy]homocalix[4]arenas. Anales de Química Int. Ed. 93, 301–309 (1997); (b) Yamato, T., Haraguchi, M., Nishikawa, J., Ide, S., Tsuzuki, H.: Synthesis, conformational studies and inclusion properties of tris[(2-pyridylmethyl)oxy]hexahomotrioxacalix[3]arenes. Can. J. Chem. 76, 989–996 (1998); (c) Yamato, T., Haraguchi, M., Nishikawa, J., Ide, S.: Synthesis, conformational studies and inclusion properties of O-benzylated calixarene-analogous trihydroxy[3.3.3]metacyclophanes. J. Chem. Soc., Perkin Trans. 1, 609–614 (1998); (d) Yamato, T., Zhang, F.: Synthesis, structures and inclusion properties of hexahomotrioxacalix[3]arene triamide derivatives having the hydrogen-bonding groups. J. Incl. Phenom. 55–64 (2001); (e) Yamato, T., Kitajima, F., Gil, J.T.: Alkyl ammonium ion selectivity of hexahomotrioxacalix[3]arene triamide derivative having the intramolecular hydrogen-bonding group. J. Incl. Phenom. 53, 257–262 (2005); (f) Yamato, T., Rahman, S., Xi, Z., Kitajima, F., Gil, J.T.: Ditopic receptors of hexaamide derivatives derived from hexahomotrioxacalix[3]arene triacetic acid. Can. J. Chem. 84, 58–64 (2006).

  15. Selected reviews. (a) Lehn, J.-M.: Perspectives in supramolecular chemistry – from molecular recognition towards molecular information processing and self-organization. Angew. Chem., Int. Ed. Engl. 29, 1304–1319 (1990); (b) Whitesides, G.M., Simanek, E.E., Mathias, J.P., Seto, C.T., Chin, D.N., Mammen, M., Gordon, D.M.: Noncovalent synthesis: using physical-organic chemistry to make aggregates. Acc. Chem. Res. 28, 37–44 (1995); (c) Hamann, B.C., Shimizu, K.D., Rebek, J. Jr.: Reversible encapsulation of guest molecules in a calixarene dimmer. Angew. Chem. Int. Ed. Engl. 35, 1326–1329 (1996); (d) Iwanek, W.: Chiral calixarenes derived from resorcinol. Part 3: functionalization of octaester derivatives with chiral amines and amino alcohols. Tetrahedron Asymm. 9, 3171–3174 (1998); (e) Prints, L.J., Reinhoudt, D.N., Timmerman, P.: Noncovalent synthesis using hydrogen bonding. Angew. Chem., Int. Ed. Engl. 40, 2382–2426 (2001); (f) Archer, E.A., Krische, M.J.: Hydrogen bonding in noncovalent synthesis: selectivity and the directed organization of molecular strands. Tetrahedron 57, 1139–1159 (2001).

  16. Conn, M.M., Rebek, J. Jr.: Self-assembling capsules. Chem. Rev. 97, 1647–1668 (1997) and references therein.

    Article  CAS  Google Scholar 

  17. Vreekamp, R.H., Verboom, W., Reinhoudt, D.N.: Lower rim-upper rim hydrogen-bonded adducts of calix[4]arenes, J. Org. Chem. 61, 4282–4288 (1996).

    Article  CAS  Google Scholar 

  18. Pedersen, C.J.: Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 7017–7036 (1967).

    Article  CAS  Google Scholar 

  19. Xu, K.: Nonaqueous liquid electrolytes for lithium-based rechargeable batteries. Chem. Rev. 104, 4303–4418 (2004).

    Article  CAS  Google Scholar 

  20. (a) Fujimoto, M., Nogami, T., Mikawa, H.: New anionic conductors: crown ether complexes of alkali-metal iodides and alkaline-earth metal iodides. Chem. Lett. 547–550 (1982); (b) Lee, H.S., Yang, X.Q., McBreen, J., Choi, L.S., Okamoto, Y.: The synthesis of a new family of anion receptors and the studies of their effect on ion pair dissociation and conductivity of lithium salts in nonaqueous solutions. J. Electrochem. Soc. 143, 3825–3829 (1996).

    Google Scholar 

  21. Bajaj, A.V., Poonia, N.S.: Comprehensive coordination chemistry of alkali and alkaline earth cations with macrocyclic multidentates: latest position. Coord. Chem. Rev. 87, 55–213 (1988).

    Article  CAS  Google Scholar 

  22. (a) Hilgenfeld, R., Saenger, W.: Structural chemistry of natural and synthetic ionophores and their complexes with cations. Top. Curr. Chem. 101, 1–82 (1982); (b) Akutagawa, T., Hasewaga, T., Nakamura, T., Takeda, S., Inabe, T., Sugiura, K., Sakata, Y., Underhill, A.E.: M+(12-crown-4) supramolecular cations (M+ = Na+, K+, Rb+, and NH4 +) within Ni(2-thioxo-1,3-dithiole-4,5-dithiolate)2 molecular conductor. Inorg. Chem. 39, 2645–2651 (2000).

    Google Scholar 

  23. (a) Iki, N., Narumi, F., Fujimoto, T., Morohashi, N., Miyano, S.: Selective synthesis of three conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]thiacalix[4]arene and their complexation properties towards alkali metal ion. J. Chem. Soc., Perkin Trans. 2, 2745–2750 (1998); (b) Morohashi, N., Iki, N., Kabuto, C., Miyano, S.: Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration. Tetrahedron Lett. 41, 2933–2937 (2000); (c) Morohashi, N., Katagiri, H., Iki, N., Yamane, Y., Kabuto, C., Hattori, T., Miyano, S.: Synthesis of all stereoisomers of sulfinylcalix[4]arenes. J. Org. Chem. 68, 2324–2333 (2003).

    Google Scholar 

  24. (a) Yamato, T., Zhang, F., Kumamaru, K., Yamamoto, H.: Synthesis, conformational studies and inclusion properties of tetrakis[(2-pyridylmethyl)oxy]thiacalix[4]arenes. J. Incl. Phenom. Macrocyclic Chem. 42, 51–60 (2002); (b) Pérez-Casas, C., Yamato, T.: Hard–Soft receptors, tetrakis[(N,N-diethylamino-carbonyl)methoxy]thiacalix[4]arene derivatives with cone and 1,3-alternate conformation. J. Incl. Phenom. Macrocyclic Chem. 53, 1–8 (2005); (c) Pérez-Casas, C., Yamamoto, H., Yamato, T.: Regioselective synthesis of distal-bisalkoxytetrathiacalix[4]arenes by a protection–deprotection method using benzyl gropus. J. Chem. Res. 694–696 (2005); (d) Yamato, T., Pérez-Casas, C., Gil, J.T., Elsegood, M.R.J., Dale, S.H., Redshaw, C.: Synthesis, structures and inclusion properties of distal-bis[(2-pyridylmethyl)oxy]tetrathiacalix[4]arenes. J. Chem. Res. 270–273 (2006); (e) Yamato, T., Pérez-Casas, C., Yamamoto, H., Elsegood, M.R.J., Dale, S.H., Redshaw, C.: Regioselective synthesis and inclusion properties of distal-bis[(2-pyridylmethyl)oxy]tetrathiacalix[4]arenes. J. Incl. Phenom. Macrocyclic Chem. 54, 261–269 (2006); (f) Yamato, T., Pérez-Casas, C., Elsegood, M.R.J., Dale, S.H., Redshaw, C.: Synthesis and inclusion properties of a novel thiacalix[4]arene-based hard–soft receptor with 1,3-alternate conformation. J. Incl. Phenom. Macrocyclic Chem. 55, 31–36 (2006).

    Google Scholar 

  25. Ashton, P., Huff, J., Menzer, S., Parsons, I.W., Preece, J.A., Stoddart, J.F., Tolley, M.S., White, A.J.P., Williams, D.J.: Bis[2]catenanes and a bis[2]rotaxane-model compounds for polymers with mechanically interlocked components. Chem. Eur. J. 2, 31–44 (1996).

    Article  CAS  Google Scholar 

  26. Narumi, F., Masumura, N., Morohashi, N., Kameyama, H., Miyano, S.: First synthesis of 25,26-bridged thiacalix[4]crowns by the use of a 25,26-O-disiloxane-diyl-capped p-tert-butylthiacalix[4]arene. J. Chem. Soc., Perkin Trans. 1, 1843–1844 (2002).

    Article  Google Scholar 

  27. (a) Tashiro, M., Yamato, T.: Metacyclophanes and related compounds. 1. Preparation and nuclear magnetic resonance spectra of 8,16-disubstituted [2.2]metacyclophanes. J. Org. Chem. 46, 4556–4562 (1981); (b) Tashiro, M., Yamato, T.: Metacyclophanes and related compounds. 8. Preparation and reactions of 8,16-diformyl[2.2]metacyclophanes. J. Org. Chem. 48, 1461–1468 (1983).

    Google Scholar 

  28. Danil de Namor, A.F., Llosa Tanco, M.A., Ng, J.C.Y., Salomón, M.: Lithium-coronand electrolytes: thermodynamic and electrochemical aspects. Pure Appl. Chem. 67, 1095–1102 (1995).

    Article  CAS  Google Scholar 

  29. Iki, N., Morohashi, N., Narumi, F., Fujimoto, T., Suzuki, T., Miyano, S.: Novel molecular receptors based on a thiacalix[4]arene platform. Preparations of the di- and tetracarboxylic acid derivatives and their binding properties towards transition metal ions. Tetrahedron Lett. 40, 7337–7341 (1999).

    Article  CAS  Google Scholar 

  30. (a) IR spectra of 11 and 12 show an intense band at 1755 and 1758 cm−1 (νC=O), respectively, suggesting their monomeric form. (b) 1H NMR of 11 and/or 12 in DMSO-d6 showed a signal at δ 12.55 and 12.61 ppm, respectively, might be due to an intermolecular hydrogen bonding between CO2H protons and DMSO. (c) Titration of 11 with AgSO3CF3 and/or KSO3CF3 did not cause any change in the 1H NMR spectra.

  31. Johnson, S.L., Rumon, K.A.: Infrared spectra of solid 1:1 pyridine-benzoic acid complexes; the nature of the hydrogen bond as a function of the acid–base levels in the complex. J. Phys. Chem. 69, 74–86 (1965).

    Article  CAS  Google Scholar 

  32. The possible hydrogen bonding formation between the carboxylic acid protons and the nitrogen of the 2-pyridyl ring was ruled out since the unfavorable orientation of the 2-pyridyl moieties.

  33. (a) Schneider, H.J., Durr, H. (eds.): Frontiers in Supramolecular Organic Chemistry and Photochemistry, pp. 123–143. VCH, New York (1991); (b) Binding Constants: The Measurement of Molecular Complex stability. Wiley, New York, Chapter 5 (1987).

  34. (a) The association constants (K ass) for 9⊃Ag+ and K+⊂9 were calculated by non-linear fitting analysis of the observed chemical shift changes of 4-pyridyl (H2,6) protons of 9, respectively, as a function of increased of cations. (b) The stoichiometry of cation complexes was determined by Job plots from 1H NMR titration data.

  35. Munakata, M., Ning, G.L., Suenega, Y., Kuroda-Sowa, T., Mackawa, M., Ohta, T.: A one-dimensional metallocyclophane with columnar aromatic stacking: the silver(i) (2-coordination complex of 1,2-benztriphenylene. Angew. Chem. Int. Ed. Engl. 39, 4555–4557 (2000).

    Article  CAS  Google Scholar 

  36. The K ass of 11⊃Ag+ was calculated base on the chemical shift of the CH2 (2-Py) protons upon titration of dimer 13 with AgSO3CF3. Similar value was obtained for the formation of 11⊃Ag+ in the independent titration experiment of 11 with AgSO3CF3 (Kass = 1.46 × 104 M−1).

  37. Benesi, H.A., Hildebrand, J.H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 41, 2073–2707 (1949).

    Google Scholar 

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  1. Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga, 840-8502, Japan

    Carol Pérez-Casas, Shofiur Rahman, Nazneen Begum, Zeng Xi & Takehiko Yamato

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  1. Carol Pérez-Casas
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Pérez-Casas, C., Rahman, S., Begum, N. et al. Allosteric bindings of thiacalix[4]arene-based receptors with 1,3-alternate conformation having two different side arms. J Incl Phenom Macrocycl Chem 60, 173–185 (2008). https://doi.org/10.1007/s10847-007-9367-3

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