The supramolecular structure of the inclusion complex of β-cyclodextrin (β-CD) with 1,1’,2,2’-tetramethyl-3,3’-( p-phenylenedimethylene) diimidazolium dibromide (TetraPhimBr), a dicationic ionic liquid, has been investigated. The inclusion complex with 1:1 molar ratio was prepared by a kneading method. Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction (XRD) analysis, 1H NMR and thermogravimetric analysis (TGA) confirmed the formation of the inclusion complex. The results showed that the host-guest system is a fine crystalline powder. The decomposition temperature of the inclusion complex is lower than that of its parent molecules, TetraPhimBr and β-CD individually.
References
[1]
Diederich, F. Molecular recognition in aqueous solution-supramolecular complexation catalysis. J. Chem. Ed？1990, 67, 813–820.
Oike, H; Aida, T. Supramolecular and macromolecular approaches toward functional nanomaterials. J. Syn. Org. Chem. Jpn？2004, 62, 459–463.
[4]
Song, LX; Bai, L; Xu, XM; He, J; Pan, SZ. Inclusion complexation, encapsulation interaction and inclusion number in cyclodextrin chemistry. Coord. Chem. Rev？2009, 253, 1276–1284.
[5]
Szejtli, J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev？1998, 98, 1743–1753.
[6]
Bender, ML; Komiyama, M. Cyclodextrin Chemistry; Springer-Verlag: Berlin, Germany, 1978.
[7]
Lipkowitz, KB. Applications of computational chemistry to the study of cyclodextrins. Chem. Rev？1998, 98, 1829–1874.
[8]
Wasserscheid, P; Keim, W. Ionic liquids-“solutions” for transition metal catalysis. Angew. Chem.-Int. Ed？2000, 39, 3772–3789.
[9]
Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev？1999, 99, 2071–2084.
[10]
Allen, D; Baston, G; Bradley, AE; Gorman, T; Haile, A; Hamblett, I; Hatter, JE; Healey, MJF; Hodgson, B; Lewin, R; Lovell, KV; Newton, B; Pitner, WR; Rooney, DW; Sanders, D; Seddon, KR; Sims, HE; Thied, RC. An investigation of the radiochemical stability of ionic liquids. Green Chem？2002, 4, 152–158.
[11]
Rogers, RD; Seddon, KR. Ionic Liquids: Applications for Green Chemistry, ACS Symposium, Series 818; American Chemical Society: Washington, DC, USA, 2002.
[12]
Gao, YA; Li, ZH; Du, JM; Han, BX; Li, GZ; Hou, WG; Shen, D; Zheng, LQ; Zhang, GY. Preparation and characterization of inclusion complexes of β-cyclodextrin with ionic liquid. Chem. Eur. J？2005, 11, 5875–5880.
[13]
Li, N; Zhao;, X; Gao;, Y; Zheng, L; Zhang, J; Yu, L. Complex formation of ionic liquid surfactant and β-cyclodextrin. Colloids Surf. A: Physicochem. Eng. Aspects？2007, 292, 196–201.
[14]
Berthod, A; He, L; Armstrong, DW. Ionic liquids as stationary phase solvents for methylated cyclodextrins in gas chromatography. Chromatographia？2001, 53, 63–68.
[15]
Qi, SD; Cui, SY; Chen, XG; Hu, ZD. Rapid and sensitive determination of anthraquinones in Chinese herb using 1-butyl-3-methylimiazolium-based ionic liquid with β-cyclodextrin as modifier in capillary zone electrophoresis. J. Chromatogr. A？2004, 1059, 191–198.
[16]
Tran, CD; Lacerda, SD. Near-infrared spectroscopic investigation of inclusion complex formation of cyclodextrins in room-temperature ionic liquid. J. Incl. Phenom. Macrocycl. Chem？2002, 44, 185–190.
[17]
Tran, CD; Lacerda, SD. Determination of binding constants of cyclodextrins in room-temperature ionic liquids by near-infrared spectrometry. Anal. Chem？2002, 74, 5337–5341.
[18]
Anderson, JL; Ding, R; Ellern, A; Armstrong, DW. Structure and properties of high stability geminal dicationic ionic liquids. J. Am. Chem. Soc？2005, 127, 593–604.
[19]
Payagala, T; Huang, J; Breitbach, ZS; Sharma, PS; Armstrong, DW. Unsymmetrical dicationic ionic liquids: Manipulation of physicochemical properties using specific structural architectures. Chem. Mater？2007, 19, 5848–5850.
[20]
Ahmed, SM; Naggi, A; Guerrini, M; Focher, B. Inclusion complexes of bioprimine with β-Cyclodextrin in solution and in solid state. Int. J. Pharm？1991, 77, 247–254.
[21]
Williams, RO, III; Mahaguna, V; Sriwongjanya, M. Characterization of an inclusion complex of cholesterol and hydroxypropyl-β-Cyclodextrin. Eur. J. Pharm. Biopharm？1998, 46, 355–360.
[22]
Nostro, PL; Santoni, I; Bonini, M; Baglioni, P. Inclusion compound from a semifluorinated alkane and β-cyclodextrin. Langmuir？2003, 19, 2313–2317.
[23]
Okumura, H; Kawaguchi, Y; Harada, A. Preparation and characterization of inclusion complexes of poly(dimethylsiloxane)s with cyclodextrins. Macromolecules？2001, 34, 6338–6343.
[24]
Chen, M; Diao, G; Zhang, E. Study of inclusion complex of β-cyclodextrin and nitrobenzene. Cemosphere？2005, 63, 522–529.
[25]
Gao, Y; Zhao, X; Dong, B; Zheng, L; Li, N; Zhang, S. Inclusion complexes of β-cyclodextrin with ionic liquid surfactants. J. Phys. Chem. B？2006, 110, 8576–8581.
[26]
Ishizu, T; Kintsu, K; Yamamoto, H. NMR study of the solution structures of the inclusion complexes of β-cyclodextrin with (+)-catechin and (？)-epicatechin. J. Phys. Chem. B？1999, 103, 8992–8997.
[27]
Jiao, H; Goh, SH; Valiyaveettil, S. Inclusion complexes of poly(4-vinylpyridine)-dodecylbenzenesulfonic acid complex and cyclodextrins. Macromolecules？2002, 35, 1980–1983.
[28]
Okumura, H; Kawaguchi, Y; Harada, A. Preparation and characterization of the inclusion complexes of poly(dimethylsilane)s with cyclodextrins. Macromolecules？2003, 36, 6422–6429.
[29]
Li, J; Ni, X; Zhou, Z; Leong, KW. Preparation and characterization of polypseudorotaxanes based on block-selected inclusion complexation between poly(propylene oxide)-poly(ethylene oxide)-poly(propylene oxide) triblock copolymers and α-cyclodextrin. J. Am. Chem. Soc？2003, 125, 1788–1795.
Cwiertnia, B; Hladon, T; Stobiecki, M. Stability of diclofenac sodium in the inclusion complex with β-cyclodextrin in the solid state. J. Pharm. Pharmacol？1999, 51, 1213–1218.
