Synthesis and characterization of mesoporous silica functionalized with Calix[4]arene derivatives

International Journal of Molecular Sciences

Volumn 13, Issue 10, 2012, Pages 13726-13736

  Alahmadi, Sana M ^a   Mohamad, Sharifah ^b   Maah, Mohd Jamil ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b TAIBAH UNIVERSITY   (Saudi Arabia)

Author keywords

Calix 4 arene; MCM 41; P sulfonatocalix 4 arene; Para tert butyl calix 4 arene

Indexed keywords

CALIX[4]ARENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILICON DIOXIDE; UNCLASSIFIED DRUG; CALIX(4)ARENE; CALIXARENE; MCM-41; PHENOL DERIVATIVE;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; COVALENT BOND; INFRARED SPECTROSCOPY; PHYSICAL CHEMISTRY; POROSITY; REACTION TIME; SURFACE PROPERTY; THERMAL ANALYSIS; THERMOGRAVIMETRY; X RAY DIFFRACTION; CHEMISTRY; SYNTHESIS;

CALIXARENES; PHENOLS; POROSITY; SILICON DIOXIDE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMOGRAVIMETRY; X-RAY DIFFRACTION;

EID: 84870654339     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms131013726     Document Type: Article

References (34)

1. Koh, K.N.; Araki, K.; Ikeda, A.; Otsuka, H.; Shinkai, S. Reinvestigation of calixarene-based artificial-signaling acetylcholine receptors useful in neutral aqueous (water/methanol) solution. J. Am. Chem. Soc. 1996, 118, 755-758.
2. Wang, L.; Shi, X.F.; Jia, P.J.; Yang, Y. Preparation of calixarene-containing polymer with proton transport ability. J. Polym. Sci. A 2004, 42, 6259-6266.
3. Beer, P.D.; Szemes, F.; Passaniti, P.; Maestri, M. Luminescent Ruthenium (II) Bipyridine-Calix[4]arene Complexes as Receptors for Lanthanide Cations. Inorg. Chem. 2004, 43, 3965-3975.
4. Blasse, G.; Grabmaier, B.C. Luminescent Materials; Springer: Berlin, Germany, 1994.
5. Asfari, Z.; Bohmer, V.; Harrowfield, J.; Vicens, J. Calixarenes 2001; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001.
6. Lai, X.H.; Li, L.; Wu, C.Y. Preparation and chromatographic characteristics of calix[4]arene polysiloxane as stationary phases for capillary gas chromatography. Chromatographia 1999, 50, 82-88.
7. Kalchenko, O.I.; Lipkowski, J.; Kalchenko, V.I.; Vysotzky, M.A.; Markovsky, L.N. Effect of octakis(diethoxyphosphoryloxy)-tert-butyl-calix[8]arene in mobile phase on the reversed-phase retention behavior of aromatic compounds: Host-guest complex formation and stability constants determination. J. Chromatogr. Sci. 1998, 36, 269-273.
8. Sokoliess, T.; Menyes, U.; Roth, U.; Jira, T. Separation of cis- and trans-isomers of thioxanthene and dibenz[b,e]oxepin derivatives on calixarene- and resorcinarene-bonded high-performance liquid chromatography stationary phases. J. Chromatogr. A 2002, 948, 309-319.
9. Tanaka, Y.; Kishimoto, Y.; Otsuka, K.; Terabe, S. Strategy for selecting separation solutions in capillary electrophoresis-mass spectrometry J. Chromatogr. A 1998, 817, 49-57.
10. Mibradt, R.; Böhmer, V. Calixarenes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001; p. 663.
11. Zhao, T.; Hu, X.; Cheng, J.; Lu, X. Use of calix[4]arene to separate positional isomers in capillary electrophoresis. Anal. Chim. Acta 1998, 358, 263-268.
12. Glennon, J.D.; O'Connor, K.; Srijaranai, S.; Manley, K.; Harris, S.J.; McKervey, M.A. Enhanced Chromatographic Selectivity for Na+ Ions on a Calixarene-Bonded Silica Phase. Anal. Lett. 1993, 26, 153-162.
13. Glennon, J.D.; Horne, E.; O'Connor, K.; Kearney, G.; Harris, S.J.; McKervey, M.A. Chromatographic selectivity for amino acid esters and alkali metal ions on a silica bonded calix[4]arene tetraester stationary phase. Anal. Proc. 1994, 31, 33-35.
14. Brindle, R.; Albert, K.; Harrisb, S.J.; Triiltzsch, C.; Horned, E.; Glennon, J.D. Silica-bonded calixarenes in chromatography: I. Synthesis and characterization by solid-state NMR spectroscopy. J. Chromatogr. A 1996, 731, 41-46.
15. Huayu, H.; Chuande, Z.; Yongsheng, J.; Rong, N.; Pan, Z.; Haixia, Z. Preparation, characterization and application of p-tert-butyl-calix[4]arene-SBA-15 mesoporous silica molecular sieves. J. Hazard. Mater. 2010, 178, 680-685.
16. Su, B.-L.; Ma, X.-C.; Xu, F.; Chen, L.-H.; Fu, Z.-Y.; Moniotte, N.; Maamar, S.B.; Lamartine, R.; Vocanson, F. SBA-15 mesoporous silica coated with macrocyclic calix[4]arene derivatives: Solid extraction phases for heavy transition metal ions. J. Colloid. Interface Sci. 2011, 360, 86-92.
17. Remi, M.; Isabelle, L.; Benedicte, L.; Bernard, V. A mesoporous silica functionalized by a covalently bound calixarene-based fluoroionophore for selective optical sensing of mercury (II) in water. J. Mater. Chem. 2005, 15, 2965-2973.
18. Li, Y.-J.; Yan, B.; Wang, L. Rare earth (Eu3+, Tb3+) mesoporous hybrids with calix[4]arene derivative covalently linkingMCM-41: Physical characterization and photoluminescence property. J. Solid State Chem. 2011, 184, 2571-2579.
19. Xia, H.; Song, M. Preparation and characterisation of polyurethane grafted single-walled carbon nanotubes and derived polyurethane nanocomposites. J. Mater. Chem. 2006, 16, 1843-1851.
20. Chun, Y.S.; Ha, K.; Lee, Y.J.; Lee, J.S.; Kim, H.S.; Park, Y.S.; Yoon, K.B. Diisocyanates as novel molecular binders for monolayer assembly of zeolite crystals on glass. Chem. Commun. 2002, 2002, 1846-1847.
21. Arnold, R.G.; Nelson, J.A.; Verbanc, J.J. Recent advances in isocyanate chemistry. Chem. Rev. 1957, 57, 47-76.
22. Simons, D.M.; Arnold, R.G. Relative reactivity of the isocyanate groups in toluene-2,4-diisocyanate. J. Am. Chem. Soc. 1956, 78, 1658-1659.
23. Che, J.; Xiao, Y.; Wang, X.; Pan, A.; Yuan, W.; Wu, X. Grafting polymerization of polyacetal onto nano-silica surface via bridging isocyanate. Surf. Coat. Technol. 2007, 201, 4578-4584.
24. Boven, G.; Oosterling, M.L.C.M.; Challa, G.; Schonten, A.J. Grafting kinetics of poly(methyl methacrylate) on microparticulate silica. Polymer 1990, 31, 2377-2383.
25. Furer, V.L.; Borisoglebskaya, E.I.; Zverev, V.V.; Kovalenko, V.I. DFT and IR spectroscopic analysis of p-tert-butylthiacalix[4]arene. Spectrochim. Acta Part A 2006, 63, 207-212.
26. Kresge, C.T.; Leonowicz, M.L.; Roth, W.J.; Beck, J.S. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature 1992, 359, 710-712.
27. Lim, M.H.; Stein, A. Comparative studies of grafting and direct syntheses of inorganic-Organic hybrid mesoporous materials. Chem. Mater. 1999, 11, 3285-3295.
28. Marler, B.; Oberhagemann, U.; Vortmann, S.; Gies, H. Influence of the sorbate type on the XRD peak intensities of loaded MCM-4. Micropor. Matter. 1996, 6, 375-383.
29. Zhang, W.H.; Lu, X.B.; Xiu, J.H.; Hua, Z.L.; Zhang, L.X.; Robertson, M.; Shi, J.L.; Yan, D.S.; Holmes, J.D. Synthesis and characterization of bifunctionalized ordered mesoporous materials. Adv. Funct. Mater. 2004, 14, 544-552.
30. Yang, H.; Zhang, G.; Hong, X.; Zhu, Y. Dicyano-functionalized MCM-41 anchored-palladium complexes as recoverable catalysts for Heck reaction. J. Mol. Catal. A 2004, 210, 143-148.
31. Sakthivel, A.; Hijazi, A.K.; Hanzlik, M.; Chiang, A.S.T.; Kühn, F.E. Heterogenization of [Cu(NCCH3)6][B(C6F5)4]2 and its application in catalytic olefin aziridination. Appl. Catal. A 2005, 294, 161-167.
32. Caps, V.; Tsang, S.C. Heterogenisation of Os species on MCM-41 structure for epoxidation of trans-stilbene. Appl. Catal. A 2003, 248, 19-31.
33. Makha, M.; Raston, C.L. Direct synthesis of calixarenes with extended arms: p-Phenylcalix[4,5,6,8]arenes and their water-soluble sulfonated derivatives. Tetrahedron Lett. 2001, 42, 6215-6217.
34. Yang, M.; Gao, Y.; He, J.P.; Li, H.M. Preparation of polyamide 6/silica nanocomposites from silica surface initiated ring-opening anionic polymerization. eXPRESS Polym. Lett. 2007, 1, 433-442.