The Syntheses and Characterization of Three Novel Macrocyclic Polyether Ligands and Some of Their Alkaline Metal Complexes

Document Type : Research Article

Authors

Department of Chemistry, Faculty of Sciences and Arts, University of Selçuk, 42079 Konya, TURKEY

Abstract

The macrocyclic ligands 2,3,5,6-Bis{3’-bromo-5’-tert-butyl benzo-5-phenyl benzo} 12C3 (L1), 2,3,5,6-bis{3’-bromo-5’-tert butyl-benzo-5’-phenyl-benzo}15C4 (L2), 2,3,5,6-bis{3’-bromo-5’-tert butyl-benzo-5’-phenyl-benzo}18C5 (L3) have been synthesized and their alkaline metal compounds with NaClO4∙H2O and KClO4  have been prepared. Chemical formulas of all compounds have been characterized by using elemental analyses and spectroscopic techniques.

Keywords

Main Subjects


[1] Pedersen, C.J., Cyclic Polyethers and Their Complexes with Metal Salts, J. Amer. Chem. Soc., 89, p. 2495, p.7017 (1967).
[2] Knipe, A.C., Crown Ethers, A New Aid to Synthesis and to Elucidation of Reaction Mechanisms, J. Chem. Educ., 53, 618 (1976). 
[3] Bilgin, A., Ertem, B., Ağın, D.F., Gök, Y., KarslıoÄŸlu, S., Synthesis, Characterization and Extraction Studies of a New vic-dioxime and its Complexes Containing Bis(Diazacrown Ether) MoietiesPolyhedron, 25, 3165 (2006).
[4] Arisa, J., Rojrit, R. and Mongkol, S. Stilbene-Bridged 1,3-Alternate Calix[4]Arene Crown Ether for Selective Alkali Ion Extraction, Tetrahedron Lett., 48, 1817 (2007).
[5] Çakır, Ü., Özer, M., Ä°çen, M.A., UÄŸraÅŸ, H.Ä°., Bulut, M., SynSynthesis of Some 3-Phenyl Chromenone-Crown Ethers and Equilibrium Studies on Complexation with Ion-Pair Extraction of Sodium and Potassium Dyes, Dyes and Pig., 60, 177 (2004).
[6] Izatt, R.M., Bordunov, A.V., Zhu, C. Y., Hathaway, J.K., “Comprehesive  Supramolecular Chemisty”, Gokel, G. W, Ed., Pergamon, New York, 1, 3595 (1996).
[7] Weber, E., Kohler, H.J., Benzo Condensed Crown-Ethers Containing 1,8-Naphthyndine or 4-Pyridone Units-Synthesis  and Complex-Formation withOrganic Guest Molecules, J. Prakt. Chem., 337, 451 (1995).
[8] Su, A.C.L., Weiher, J.F., Cobaltous Complexes of Cyclic Polyethers, Inorg. Chem., 7, 176 (1968).
[9] De Vos, D., J. Van Daalen, A.C. Knegt, Th.C. Van Hegningen, L.P., Complexes of Some Divalent Metals with 18-Crown-6, J. Inorg. Nucl. Chem., 37(5), 1319 (1975).
[10] Loïc,  J. C.  and  Raymond,  F. Z.,  Cyclic  di[(o-polyethyleneglycoxy)phenyl]amine: New Members in the Crown Eher Family, Tetrahedron Lett., 41, 2373 (2000).
[11] Moriarty, R., Rao, M., Tuladhar, M.S., D’Silva, C.S.M., WÄ°lliams, G., Gilardi R., Crown Ether Ionophores, Construction of Neutral Corrier Ion-Selective Electrodes, J. Am. Chem. Soc., 115, 1194 (1993).
[12] Hayakawa, K., Kido, K., Kanematsu, K., Cyclo-addition Reactions of a Crowned p-Benzoquinone, J. Chem. Soc., Chem. Commun., 3, 268 (1986).
[13] Marchand, A. P.,  Alihodzic, S.,  McKim, A. S., Kumar, K.A., Mlinarich- Majerski, K., Sumanovac, T., Bott, S. G., Synthesis and Alkali Metal Picrate Extraction Capabilities of a 4-Oxahexacyclo [5.4.1.02, 6.03,10.05,9.08,11]dodecane-derived Cryptand, A New Ionophore for Selective Ion Complexation, Tetrahedron Lett., 39, 1861 (1998).
[14] Liming,  Y.,  Yuru,  K.,  Yuling,  W.,  Liwen, X., Hidetoshi, K., Ken-ichi, O., Synthesis of Crown Ether-Containing Copolyimides and Their Peryaporation Properties to Benzene/Cyclohexane Mixture, J. Membr. Sci., 249, 33 (2005).
[15] Zhi Bin, H., Tai Jong, K. and Seung Hyun, C., The Synthesis of Unique Structures of Tetra-Crown Ethers Through Michael Addition, Tetrahedron Lett., 46, 3461 (2005).
[16] Karakaplan, M. and Aral, T., Synthesis of New Chiral Crown Ethers Containing a (p-methoxy-phenoxy)methyl Moiety and Their Chiral Recognition Ability Towards Amino Acid Esters, Tetrahedron: Asymmetry, 16, 2119 (2005).
[17] Mohamed, F.S., Philippe, V., Abdelhakim, A. and Claude D., Nucleophilic Opening of Bis-Epoxides: A New Access to Symmetrically Functionalized Macrocycles, Tetrahedron Lett., 41, 1019 (2000).
[18] Sheng-Tung, H., Hsien-Shou, K., Chiao-Long, H. and Yuh-Ling, L., Efficient Synthesis of ‘Redox-Switched’ Naphthoquinone Thiol-Crown Ethers and Their Biological Activity Evaluation, Bioorg. Med. Chem., 10, 1947 (2002).
[19] Smid, J., Ion-Binding Properties of Crown Ether and Cryptand Containing Polymers, Ind. Eng. Chem. Prod. Res. Dev., 19, 364 (1980).
[20] Blasiu, E., Janzen, K.P., Adrian, W., Klein, W., Klotz, H., Luxenburger, H., Mernke, E., Nguyen, V., Nguyentien, T., Rausch, R., Stockemer, J., Toussaint, A., Talanta., 27, 127 (1980). 
[21] Gokel, G.W., Timko, J.M. and Cram, D.J., Chiral Recognition in Amino-Ester Complexation by a Cyclic Polyether Host Compound, J. C. S. Chem. Commun., 10, 394 (1975).
[22] Sousa, L.R., Hoffman, D.H., Kaplan, L. and Cram, D.J., Total Optical Resolution of Amino Esters by Designed Host-Guest Relations in Molecular Complexation, J. Amer. Chem. Soc., 96, 7100 (1974).
[23] Erk, Ç., Habilitation Thesis, University of Ankara, Ankara, Turkey (1974).
[24] Sezgin, M., Bedük, A.D., Ertul, Åž., Koçak, A., The Synthesis of 3 New Macrocyclic Ligands and Preparation of Some of Their Cationic Complexes, Synth. React. Inorg. Met. Org. Chem., 23 (2), 269 (1993).
[25] Sezgin, M. and Erk, Ç., Polyoxalactones and Their Cationic Complexes, Polym. Bull., 4, 645 (1981).