Decoration of MCM?41 Pore Entrances with Amino-Containing Groups for pH-Controlled Release of para-Aminobenzoic Acid

Authors

  • N. V. Roik Chuiko Institute of Surface Chemistry of National Academy of Sciences of Ukraine
  • L. A. Belyakova Chuiko Institute of Surface Chemistry of National Academy of Sciences of Ukraine
  • M. O. Dziazko Chuiko Institute of Surface Chemistry of National Academy of Sciences of Ukraine
  • O. I. Oranska Chuiko Institute of Surface Chemistry of National Academy of Sciences of Ukraine

DOI:

https://doi.org/10.15407/hftp05.04.404

Keywords:

sol-gel synthesis, vapour-phase modification, desorption, surface properties

Abstract

Selectively modified silica materials with uniform hexagonally ordered cylindrical mesopores were synthesized by combination of sol?gel condensation and postsynthetic chemical modification. Hexagonally arranged porous structure of silica carriers was confirmed by X-ray diffraction and low?temperature ad?desorption of nitrogen. Content of functional groups immobilized onto external surface of silica particles was determined from chemical analysis of surface reaction products. Release capability of MCM?41 mesoporous silicas selectively modified with N?(2?aminoethyl)?3?aminopropyl or N?[N’-(N’-phenyl)-2-aminophenyl]?3?aminopropyl groups was studied by use of para?aminobenzoic acid as model biologically active substance. It has been found that desorption of aromatic amino acid from mesoporous channels of silica can be regulated using pH-sensitive functional groups which are chemically bounded with outer silica surface.

References

1. Kresge C.T., Leonowicz M.E., Roth W.J., Vartuli J.C., Beck J.S. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature. 1992. 359: 710. https://doi.org/10.1038/359710a0

2. Iskandar F. Ordered nanoporous particles. Encyclopedia of Nanoscience and Nanotechnology. 2004. 8: 259.

3. Lin H.P., Cheng S., Mou C.-Y. Synthesis of thermally stable MCM 41 at ambient temperature. J. Chin. Chem. Soc. 1996. 43(5): 375. https://doi.org/10.1002/jccs.199600054

4. Van Der Voort P., Mathieu M., Mees F., Vansant E.F. Synthesis of high quality MCM 48 and MCM 41 by means of the GEMINI surfactant method. J. Phys. Chem. B. 1998. 102(44): 8847. https://doi.org/10.1021/jp982653w

5. Jana S.K., Nishida R., Shindo K., Kugita T., Namba S. Pore size control of mesoporous molecular sieves using different organic auxiliary chemicals. Microporous Mesoporous Mater. 2004. 68(1–3): 133. https://doi.org/10.1016/j.micromeso.2003.12.010

6. Beck J.S., Vartuli J.C., Roth W.J., Leonowicz M.E., Kresge C.T., Schmitt K.D., Chu C.T.W., Olson D.H., Sheppard E.W., McCullen S.B., Higgins J.B., Schlenker J.L. A new family of mesoporous molecular sieves prepared with liquid crystal templates. J. Am. Chem. Soc. 1992. 114(27): 10834. https://doi.org/10.1021/ja00053a020

7. Corma A., Kan Q., Navarro M.T., Pérez-Pariente J., Rey F. Synthesis of MCM-41 with different pore diameters without addition of auxiliary organics. Chem. Mater. 1997. 9(10): 2123. https://doi.org/10.1021/cm970203v

8. Gao T., Wen C., Long C., Jing Z., Jingkun G. Effects of assistant agent on mesoporous structure of silica MCM 41 molecular sieves. Journal of Wuhan University of Technology-Mater. Sci. Ed. 2005. 20(2): 60.

9. Huo Q., Margolese D.I., Stucky G.D. Surfactant control of phases in the synthesis of mesoporous silica based materials. Chem. Mater. 1996. 8(5): 1147. https://doi.org/10.1021/cm960137h

10. Sayari A., Liu P. Characterization of large pore MCM-41 molecular sieves obtained via hydrothermal restructuring. Chem. Mater. 1997. 9(11): 2499. https://doi.org/10.1021/cm970128o

11. Sutra P., Fajula F., Brunel D., Lentz P., Daelen G., Nagy J.B. 29Si and 13C MAS-NMR characterization of surface modification of micelle-templated silicas during the grafting of organic moieties and end-capping. Colloids Surf. A. 1999. 158(1–2): 21. https://doi.org/10.1016/S0927-7757(99)00126-0

12. Yang H., Zhang G., Hong X., Zhu Y. Silylation of mesoporous silica MCM-41 with the mixture of Cl(CH2)3SiCl3 and CH3SiCl3: combination of adjustable grafting density and improved hydrothermal stability. Microporous Mesoporous Mater. 2004. 68(1–3): 119. https://doi.org/10.1016/j.micromeso.2003.12.014

13. Bae J.A., Song K.-C., Jeon J.-K., Ko Y.S., Park Y.-K., Yim J.-H. Effect of pore structure of amine functionalized mesoporous silica-supported rhodium catalysts on 1 octene hydroformylation. Micropor. Mesopor. Mater. 2009. 123(1–3): 289. https://doi.org/10.1016/j.micromeso.2009.04.015

14. Lesaint C., Lebeau B., Marichal C., Patarin J. Synthesis of mesoporous silica materials functionalized with n-propyl groups. Microporous Mesoporous Mater. 2005. 83(1–3): 76. https://doi.org/10.1016/j.micromeso.2005.01.012

15. Yoshitake H., Koiso E., Horie H., Yoshimura H. Polyamine functionalized mesoporous silicas: Preparation, structural analysis and oxyanion adsorption. Microporous Mesoporous Mater. 2005. 85(1–2): 183. https://doi.org/10.1016/j.micromeso.2005.06.009

16. Daehler A., Boskovic S., Gee M.L., Separovic F., Stevens G.W., O'Connoret A.J. Postsynthesis vapor-phase functionalization of MCM 48 with hexamethyldisilazane and 3 aminopropyldimethylethoxylsilane for bio-separation applications. J. Phys. Chem. B. 2005. 109(34): 16263. https://doi.org/10.1021/jp0511799

17. Slowing I.I., Vivero-Escoto J.L., Wu C.-W., Lin S.-Y. Mesoporous silica nanoparticles as controlled release drug delivery and gene transfection carriers. Adv. Drug Delivery Rev. 2008. 60(11): 1278. https://doi.org/10.1016/j.addr.2008.03.012

18. Patel K., Angelos S., Dichtel W.R., Coskun A., Yang Y.-W., Zink J.I., Stoddart J.F. Enzyme-responsive snap top covered silica nanocontainers. J. Am. Chem. Soc. 2008. 130(8): 2382. https://doi.org/10.1021/ja0772086

19. Zhao Y., Trewyn B.G., Slowing I.I., Lin V.S. Y. Mesoporous silica nanoparticle based double brug delivery system for glucose responsive controlled release of insulin and cyclic AMP. J. Am. Chem. Soc. 2009. 131(24): 8398. https://doi.org/10.1021/ja901831u

20. Nguyen T.D., Tseng H. R., Celestre P.C., Flood A.H., Liu Y., Stoddart J.F., Zink J.I. A reversible molecular valve. PNAS. 2005. 102(29): 10029.  https://doi.org/10.1073/pnas.0504109102

21. Nguyen T.D., Leung K.C. F., Liong M., Pentecost C.D., Stoddart J.F., Zink J.I. Construction of a pH-driven supramolecular nanovalve. Org. Lett. 2006. 8(15): 3363. https://doi.org/10.1021/ol0612509

22. Angelos S., Yang Y. W., Patel K., Stoddart J.F., Zink J.I. pH responsive supramolecular nanovalves based on cucurbit[6]uril pseudorotaxanes. Angew. Chem. Int. Ed. Engl. 2008. 47(12): 2222.  https://doi.org/10.1002/anie.200705211

23. Park C., Oh K., Lee S.C., Kim C. Controlled release of guest molecules from mesoporous silica particles based on a pH responsive polypseudorotaxane motif. Angew. Chem. Int. Ed. Engl. 2007. 46(9): 1455. https://doi.org/10.1002/anie.200603404

24. Guo W., Wang J., Lee S. J., Dong F., Park S.S., Ha Ch.S. A general pH responsive supramolecular nanovalve based on mesoporous organosilica hollow nanospheres. Chem. Eur. J. 2010. 16(29): 8641. https://doi.org/10.1002/chem.201000980

25. Meng H., Xue M., Xia T., Zhao Y.-Li., Tamanoi F., Stoddart J.F., Zink J.I., Nel A.E. Autonomous in vitro anticancer drug release from mesoporous silica nanoparticles by pH sensitive nanovalves. J. Am. Chem. Soc. 2010. 132(36): 12690.  https://doi.org/10.1021/ja104501a

26. Hernandez R., Tseng H. R., Wong J.W., Stoddart J.F., Zink J.I. An operational supramolecular nanovalve. J. Am. Chem. Soc. 2004. 126(11): 3370. https://doi.org/10.1021/ja039424u

27. Casasus R., Marcos M.D., Martinez Manez R., Ros-Lis J.V., Soto J., Villaescusa L.A., Amorós P., Beltrán D., Guillem C., Latorre J. Toward the development of ionically controlled nanoscopic molecular gates. J. Am. Chem. Soc. 2004. 126(28): 8612. https://doi.org/10.1021/ja048095i

28. Choi H.S., Huh K.M., Ooya T., Yui N. pH and thermosensitive supramolecular assembling system: rapidly responsive properties of cyclodextrin conjugated poly(E lysine). J. Am. Chem. Soc. 2003. 125(21): 6350. https://doi.org/10.1021/ja034149x

29. Park C., Lee K., Kim C. Photoresponsive cyclodextrin covered nanocontainers and their sol gel transition induced by molecular recognition. Angew. Chem. Int. Ed. Engl. 2009. 48(7): 1275. https://doi.org/10.1002/anie.200803880

30. Mal N.K., Fujiwara M., Tanaka Y. Photocontrolled reversible release of guest molecules from coumarin-modified mesoporous silica. Nature. 2003. 421(6921): 350. https://doi.org/10.1038/nature01362

31. Bragg W.L. The diffraction of short electromagnetic waves by a crystal. Proceedings of the Cambridge Philosophical Society. 1913. 17: 43.

32. Fenelonov V.B., Romannikov V.N., Derevyankin A.Yu. Mesopore size and surface area calculations for hexagonal mesophases (types MCM-41, FSM-16, etc.) using low-angle XRD and adsorption data. Microporous Mesoporous Mater. 1999. 28(1): 57. https://doi.org/10.1016/S1387-1811(98)00280-7

33. Kruk M., Jaroniec M., Sayari A. Adsorption study of surface and structural properties of MCM 41 materials of different pore sizes. J. Phys. Chem. B. 1997. 101(4): 583. https://doi.org/10.1021/jp962000k

34. Pohloudek Fabini R., Beyrich Th. Organische Analyse. (Akademische Verlagsgesellschart Geest und Portig K. G., Leipzig, 1975).

35. Williams W.J. Handbook of anion determination. (London: Butterworths, 1979). Helfferich F.G. Ion exchange. (New York: Dover Publications Inc., 1995).

36. Roik N.V., Belyakova L.A. Sol-gel synthesis of MCM-41 silicas and selective vapor phase modification of their surface. J. Solid State Chem. 2013. 207: 194. https://doi.org/10.1016/j.jssc.2013.09.027

37. Roik N.V., Belyakova L.A. Interaction of supramolecular centers of silica surface with aromatic amino acids. J. Colloid Interface Sci. 2011. 362(1): 172. https://doi.org/10.1016/j.jcis.2011.05.085

Downloads

How to Cite

(1)
Roik, N. V.; Belyakova, L. A.; Dziazko, M. O.; Oranska, O. I. Decoration of MCM?41 Pore Entrances With Amino-Containing Groups for PH-Controlled Release of Para-Aminobenzoic Acid. Him. Fiz. Tehnol. Poverhni 2014, 5, 404-414.

Issue

Vol. 5 No. 4 (2014): Chemistry, Physics and Technology of Surface / Himia, Fizika ta Tehnologia Poverhni

Section

Articles

License

  1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
  2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
  3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work.