Synthesis of hybrid nano- and microsized particles on the base of colloid silica and thiacalix[4]arene derivatives
Source abstract
Abstract
Two approaches to controlled synthesis of the organo-inorganic materials obtained by one- and two-stage surface modification of nanosized silica particles by p-tert-butyl thiacalix[4]arene derivatives have been developed and compared. The possibility of the synthesis of the mono- or low-disperse hybrid organo-inorganic particles with hydrodynamic diameter varying in the range of 23.92-137.1 nm depending on stereoisomer and reaction mixture dilution was shown via surface modification of the silica particles. The direct acylation of aminated silica leads to covalent macrocycle-silica hybrid clusters of micron size. The grafting reaction was confirmed by IR-, UV-spectroscopies, dynamic light scattering and thermal analysis. © 2013 Springer Science+Business Media Dordrecht.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Mesoporous Materials and Catalysis · Catalysis and Oxidation Reactions · Supramolecular Chemistry and Complexes
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References (28)
Show source-provided references
1. An Y, Chen M, Xue Q, Liu W (2007) Preparation and self-assembly of carboxylic acid-functionalized silica. J Colloid Interface Sci 311:507–51310.1016/j.jcis.2007.02.084 ↗
2. Aydogan A, Akar A (2011) Siloxane-functionalized calix[4]pyrrole: synthesis, characterization and modification of silica-based solid supports. Tetrahedron Lett 52:2790–279310.1016/j.tetlet.2011.03.135 ↗
3. Bitar A, Ahmad NM, Fessi H, Elaissari A (2012) Silica based nanoparticles for biomedical applications. Drug Deliv Today 17:1147–115410.1016/j.drudis.2012.06.014 ↗
4. Choi J, Burns AA, Williams RM, Zhou Z et al (2007) Core–shell silica nanoparticles as fluorescent labels for nanomedicine. J Biomed Opt 12:064007-1–064007-11
5. Gorbachuk VV, Yakimova LS et al (2011) Silica nanoparticles with proton donor and proton acceptor groups: synthesis and aggregation. Silicon 3:5–1210.1007/s12633-011-9077-8 ↗
6. Huang H, Zhao C, Ji Y, Nie R et al (2010) Preparation, characterization and application of p-tert-butyl-calix[4]arene-SBA-15 mesoporous silica molecular sieves. J Hazard Mater 178:680–68510.1016/j.jhazmat.2010.01.140 ↗
7. Iki N, Morohashi N, Narumi F, Fujimoto T, Suzuki T, Miyano S (1999) 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 40:7337–734110.1016/S0040-4039(99)01503-8 ↗
8. Kumagai H, Hasegawa H et al (1997) Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulphur in the presence of a base. Tetrahedron Lett 38:3971–397210.1016/S0040-4039(97)00792-2 ↗
9. Levy L, Sahoo Y, Kim K-S, Bergey EJ, Prasad PN (2002) Nanochemistry: synthesis and characterization of multifunctional nanoclinics for biological applications. Chem Mater 14:3715–372110.1021/cm0203013 ↗
10. Lhoták P (2004) Chemistry of thiacalixarenes. Eur J Org Chem 8:1675–169210.1002/ejoc.200300492 ↗
11. Lhoták P, Stastny V, Zlatuskova P et al (2000) Synthesis and 1H NMR complexation study of thiacalix[4]arene tetraacetates. Collect Czechoslov Chem Commun 65:757–77110.1135/cccc20000757 ↗
12. Li L-S, Liu M, Da SL, Feng YQ (2004) Studies on the chromatographic behavior of nucleosides and bases on p-tert-butyl-calix[8]arene-bonded silica gel stationary phase by HPLC. Talanta 63:433–44110.1016/j.talanta.2003.11.016 ↗
13. Memon S, Yilmaz M (2001) A complimentary study of calixarene based bifunctional receptors for alkali or transition metal cations and Cr2O7 2− anions. J Mol Struct 595:101–10910.1016/S0022-2860(01)00509-9 ↗
14. Mollard A, Ibragimova D, Antipin IS, Konovalov AI, Stoikov II, Zharov I (2010) Molecular transport in thiacalix[4]arene-modified nanoporous colloidal films. Microporous Mesoporous Mater 131:378–38410.1016/j.micromeso.2010.01.018 ↗
15. Perrin DD, Armarego WLF, Perrin DR (1980) Purification of laboratory chemicals, 2nd edn. Pergamon Press, Exeter
16. Pham KN, Fullston D, Sagoe-Crentsil K (2007) Surface modification for stability of nano-sized silica colloids. J Colloid Interface Sci 315:123–12710.1016/j.jcis.2007.06.064 ↗
17. Shokova EA, Kovalev VV (2003) Thiacalix[4]arenes—a new class of synthetic receptors. Russ J Org Chem 39:1–2910.1023/A:1023416409935 ↗
18. Smith JE, Wang L, Tan (2006) Bioconjugated silica-coated nanoparticles for bioseparation and bioanalysis. Trends Anal Chem 25:848–85510.1016/j.trac.2006.03.008 ↗
19. Sreeremya TS, Thulasi KM, Krishnan A, Ghosh S (2012) A novel aqueous route to fabricate ultrasmall monodisperse lipophilic cerium oxide nanoparticles. Ind Eng Chem Res 51:318–32610.1021/ie2019646 ↗
20. Stibor I (2005) Anion sensing. Springer, Berlin10.1007/b101055 ↗
21. Stoikov II, Smolentsev VA, Antipin IS, Habicher WD, Gruner M, Konovalov AI (2006) Array of fluorescent chemosensors for the molecular recognition of halide anions on the basis of the stereoisomers of thiacalix[4]arene tetranaphthylamides. Mendeleev Commun 16:294–29710.1070/MC2006v016n06ABEH002417 ↗
22. Stoikov II, Galukhin A, Zaikov E, Antipin I (2009) Synthesis and complexation properties of 1,3-alternate stereoisomers of p-tert-butylthiacalix[4]arenes tetrasubstituted at the lower rim by the phthalimide group. Mendeleev Commun 19:193–19510.1016/j.mencom.2009.07.006 ↗
23. Stoikov II, Yantemirova AA, Nosov RV, Rizvanov IK et al (2011) p-tert-Butyl thiacalix[4]arenes functionalized at the lower rim by amide, hydroxyl and ester groups as anion receptors. Org Biomol Chem 9:3225–323410.1039/c0ob01251c ↗
24. Stolarczyk JK, Ghosh S, Brougham DF (2009) Controlled growth of nanoparticle clusters through competitive stabilizer desorption. Angew Chem Int Ed 48:175–17810.1002/anie.200803895 ↗
25. Tartaj P, Morales MP, Veintemillas-Verdaguer S, Gonzalez-Carreño T, Serna CJ (2006) Synthesis, properties and biomedical applications of magnetic nanoparticles. Handbook of magnetic materials 16, Chap 5. Elsevier B. V., Amsterdam, pp 403–48210.1016/S1567-2719(05)16005-3 ↗
26. Vertegel AA, Siegel RW, Dordick JS (2004) Silica nanoparticle size influences the structure and enzymatic activity of adsorbed lysozyme. Langmuir 20:6800–680710.1021/la0497200 ↗
27. Xiao Y-X, Xiao XZ, Feng YQ, Wang ZH, Da SL (2002) High-performance liquid chromatography of sulfonamides and quinolones on p-tert-butyl-calix[6]arene-bonded silica gel stationary phase. Talanta 56:1141–115110.1016/S0039-9140(01)00667-1 ↗
28. Zlatuskova P, Stibor I, Tkadlecova M, Lhoták P (2004) Novel anion receptors based on thiacalix[4]arene derivatives. Tetrahedron 60:11383–1139010.1016/j.tet.2004.09.088 ↗