Preparation and characterization of organic–inorganic adduct of dinaphtosulfide macrocyclic diamide and silicotungstic acid: study of interaction in solid and solution phase

References

• Zhang XM, Shan BZ, Bai ZP, You XZ, Duan CY. Electrochromism and x-ray crystal structure of a mixed-valence charge-transfer complex [(CH3)2NC6H4NHCH3)2]4 [(C4H9)4N]SiMo12O40. Chem Mater. 1997;9:2687–2689. doi: 10.1021/cm970396m
   Web of Science ®Google Scholar
• Niu J, You X, Duan C, Fun H, Zhou Z. A novel optical complex between an organic substrate and a polyoxometalate. Crystal and molecular structure of α-H4SiW12O40.4HMPA.2H2O (HMPA= Hexamethylphosphoramide). Inorg Chem. 1996;35:4211–4217. doi: 10.1021/ic951458i
   PubMed Web of Science ®Google Scholar
• Okuhara T. New catalytic functions of heteropoly compounds as solid acids. Catal Today. 2002;73:167–176. doi: 10.1016/S0920-5861(01)00509-0
   Web of Science ®Google Scholar
• Le Magueres P, Hubig SM, Lindeman SV, Veya P, Kochi JK. Novel charge-transfer materials via cocrystallization of planar aromatic donors and spherical polyoxometalate acceptors. J Am Chem Soc. 2000;122:10073–10082. doi: 10.1021/ja0019878
   Web of Science ®Google Scholar
• Taghdiri M, Saadatjou N, Zamani N, Farrokhi R. Heterogeneous degradation of precipitated hexamine from wastewater by catalytic function of silicotungstic acid in the presence of H2O2 and H2O2/Fe2+. J Hazard Mater. 2013;246–247:206–212. doi: 10.1016/j.jhazmat.2012.12.029
   PubMed Web of Science ®Google Scholar
• Taghdiri M, Saffar M. Removal of mineral salts by heteropoly acid-crown ether adduct for quick determination of trace amounts of lithium in natural brines. Orient J Chem. 2011;27:1555–1561.
   Google Scholar
• Mikulaj V, Švec V. Precipitation separation of strontium and calcium from acidic solutions using crown ether and tungstosilicic acid. J Radioanal Nucl Chem. 1994;183:127–133. doi: 10.1007/BF02043125
   Web of Science ®Google Scholar
• Rajec P, Mikulaj V, Husarčik P, Švec V. Coprecipitation of radium with calcium and strontium from acid solutions using crown ether and tungstosilicic acid. J Radioanal Nucl Chem. 1997;219:123–125. doi: 10.1007/BF02040278
   Web of Science ®Google Scholar
• Rajec P, Švec V, Mikulaj V, Hanzel R. Coprecipitation of 15-crown-5 ether complexes of lead and strontium with tungstosilicic acid. J Radioanal Nucl Chem. 1998;229:9–12. doi: 10.1007/BF02389438
   Web of Science ®Google Scholar
• Švec V, Mikulaj V, Hanzel R. Precipitation separation of lead and calcium, strontium, barium from acidic solutions using crown ether and tungstosilicic acid. J Radioanal Nucl Chem. 1996;208:487–497. doi: 10.1007/BF02040066
   Web of Science ®Google Scholar
• Jeng J, Shih JS. Sodium ion-selective electrode based on crown ether-phosphotungstic acid precipitates. Analyst. 1984;109:641–643. doi: 10.1039/an9840900641
   Web of Science ®Google Scholar
• Rani A, Kumar S, Bannerjee N. Use of a crown ether-heteropoly acid precipitate as a potassium ion-selective membrane electrode. Fresen J Anal Chem. 1987;328:33–36. doi: 10.1007/BF00560943
   Google Scholar
• Sheen SR, Shih JS. Lead (II) ion-selective electrodes based on crown ethers. Analyst. 1992;117:1691–1695. doi: 10.1039/an9921701691
   Web of Science ®Google Scholar
• Wang D, Shih JS. Caesium ion-selective electrode based on 15-crown-5-phosphotungstic acid precipitates. Analyst. 1985;110:635–638. doi: 10.1039/an9851000635
   Web of Science ®Google Scholar
• Shih JS, Tsay LM, Wu SC. Adsorption of rare earths with crown ether adsorbents. Analyst. 1985;110:1387–1390. doi: 10.1039/an9851001387
   Web of Science ®Google Scholar
• Tzeng DL, Shih JS, Yeh YC. Adsorption of heavy metal ions on crown ether adsorbents. Analyst. 1987;112:1413–1416. doi: 10.1039/an9871201413
   Web of Science ®Google Scholar
• Fernando L, Miles M, Bowen L. Ion-exchange properties of crown ether-phosphomolybdic acid precipitates. Anal Chem. 1980;52:1115–1119. doi: 10.1021/ac50057a027
   Web of Science ®Google Scholar
• Soares-Santos PCR, Cunha-Silva L, Sousa FL, Mafra L, Rocha J, Cavaleiro A, Trindade T, Paz FAA, Klinowski J, Nogueira HIS. Two novel supramolecular organic-inorganic adducts containing dibenzo-30-crown-10 and H3PM12O40 (M= W or Mo). J Mol Struct. 2008;888:99–106. doi: 10.1016/j.molstruc.2007.11.035
   Web of Science ®Google Scholar
• You W, Wang E, Zhang H, Xu L, Wang Y. Synthesis and structural characterization of a new supermolecular compound: H3PW12O40. 6C14H20O5. 16H2O (C14H20O5= benzo-15-crown-5). J Mol Struct. 2000;554:141–147. doi: 10.1016/S0022-2860(00)00668-2
   Web of Science ®Google Scholar
• You W, Wang E, He Q, Xu L, Xing Y, Jia H. Synthesis and crystal structure of a new supermolecular compound:[C12H24O6][H3PMo12O40]·22H2O (C12H24O6= 18-crown-6). J Mol Struct. 2000;524:133–140. doi: 10.1016/S0022-2860(99)00447-0
   Web of Science ®Google Scholar
• You W, Wang E, Xu L, Zhu Z, Gu Y. A molecule based on polyoxometalate acid and crown ether: synthesis and characterization of ((H3O)(C20H24O6))2(HPMo12O40). C20H24O6. 3MeCN. H2O (C20H24O6= dibenzo-18-crown-6). J Mol Struct. 2002;605:41–50. doi: 10.1016/S0022-2860(01)00756-6
   Web of Science ®Google Scholar
• Yang G, Guo H, Wang M, Huang M, Chen H, Liu B, Dong S. Assembly of 12-tungstosilicic acid and 4-aminobenzo-15-crown-5 ether based on the electrostatic attraction through bridging of oxonium ions on different substrates. J Electroanal Chem. 2007;600:318–324. doi: 10.1016/j.jelechem.2006.09.010
   Web of Science ®Google Scholar
• Shivaiah V, Das SK. Inclusion of a Cu2+ ion by a large-cavity crown ether dibenzo-24-crown-8 through supramolecular interactions. Inorg Chem. 2005;44:7313–7315. doi: 10.1021/ic051176a
   PubMed Web of Science ®Google Scholar
• Lu X, Zhong R, Liu S, Liu Y. Synthesis and structural characterization of N-(para-substituted-phenyl) aza-15-crown-5 sodium heteropolymolybdotungstate. Polyhedron. 1997;16:3865–3872. doi: 10.1016/S0277-5387(97)00165-4
   Web of Science ®Google Scholar
• Li Y, Wang E, Wang S, Lu Y, Hu C, Hu N, Jia H. Synthesis, characterization and crystal structures of dibenzo-18-crown-6 sodium isopolytungstates. J Mol Struct. 2002;607:133–141. doi: 10.1016/S0022-2860(01)00882-1
   Web of Science ®Google Scholar
• Zhu L, Lu X. A Supermolecule assembled by sodium cation, Crown ether and α-Dawson Heteropolyanion. Chin J Chem. 2012;30:512–516. doi: 10.1002/cjoc.201280007
   Web of Science ®Google Scholar
• Endo D, Akutagawa T, Kubo K, Noro S, Cronin L, Nakamura T. Molecular motions and hydrogen-bonding networks in (o-Aminoanilinium)–(Crown Ethers)–[PMo12O40]4− crystals. B Chem Soc Jpn. 2012;85:305–315. doi: 10.1246/bcsj.20110371
   Web of Science ®Google Scholar
• Sarma M, Chatterjee T, Das SK. A copper–cyclen coordination complex associated with a polyoxometalate anion: synthesis, crystal structure and electrochemistry of [Cu (cyclen)(MeCN)][W6O19]. Inorg Chem Commun. 2010;13:1114–1117. doi: 10.1016/j.inoche.2010.06.013
   Web of Science ®Google Scholar
• Chatterjee T, Sarma M, Das SK. Polyoxometalate associated ion-pair solid based on a crown ether inclusion complex: synthesis, structure and spectroscopy. J Mol Struct. 2010;981:34–39. doi: 10.1016/j.molstruc.2010.07.020
   Web of Science ®Google Scholar
• Chatterjee T, Sarma M, Das SK. Supramolecular architectures from ammonium-crown ether inclusion complexes in polyoxometalate association: synthesis, structure, and spectroscopy. Cryst Growth Des. 2010;10:3149–3163. doi: 10.1021/cg100292u
   Web of Science ®Google Scholar
• Shockravi A, Shamsipur M, Fattahi H, Taghdiri M, Heidaryan D, Alizadeh K, Rostami E, Abbaszadeh M, Yousefi A. Efficient synthesis and metal cations complexation of some novel dinaphthosulfide-substituted macrocyclic diamides. J Incl Phenom Macro. 2008;61:153–160. doi: 10.1007/s10847-008-9408-6
   Web of Science ®Google Scholar
• Gao J, Liu X, Liu Y, Yu L, Feng Y, Chen H, Li Y, Rakesh G, Huan CHA, Sum TC, Zhao Y, Zhang Q. Experimental and theoretical studies on pyrene-grafted polyoxometalate hybrid. Dalton Trans. 2012;41:12185–12191. doi: 10.1039/c2dt31474f
   PubMed Web of Science ®Google Scholar
• Hao J, Ruhlmann L, Zhu Y, Li Q, Wei Y. Naphthylimido-substituted hexamolybdate: preparation, crystal structures, solvent effects, and optical properties of three polymorphs. Inorg Chem. 2007;46:4960–4967. doi: 10.1021/ic070064b
   PubMed Web of Science ®Google Scholar
• Lu M, Kang J, Wang D, Peng Z. Enantiopure 1, 1′-binaphthyl-based polyoxometalate-containing molecular hybrids. Inorg Chem. 2005;44:7711–7713. doi: 10.1021/ic051129i
   PubMed Web of Science ®Google Scholar
• Rajkumar T, Ranga Rao G. Synthesis and characterization of hybrid molecular material prepared by ionic liquid and silicotungstic acid. Mater Chem Phys. 2008;112:853–857. doi: 10.1016/j.matchemphys.2008.06.046
   Web of Science ®Google Scholar
• Taghdiri M, Behjatmanesh-Ardakani R, Shockravi A, Taheri F, Fattahi H. Study on the interaction between dinaphthosulfide-substituted macrocyclic diamides and some metal ions: experimental measurements vs. quantum mechanical calculations. J Inclusion Phenom Macro. 2012;73:255–262. doi: 10.1007/s10847-011-0050-3
   Web of Science ®Google Scholar
• Masiker MC, Mayne CL, Eyring EM. Stability constants: comparative study of fitting methods. Determination of second-order complexation constants by 23Na and 7Li NMR chemical shift titration. Magn Reson Chem. 2006;44:220–229. doi: 10.1002/mrc.1787
   PubMed Web of Science ®Google Scholar