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Tetra-β-(2-(diethylamino)ethoxy) nickel phthalocyanine: synthesis and inclusion in MCM-41

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Abstract

In order to include phthalocyanine macromolecule in MCM-41 molecular sieve, a inclusion-suitable phthalocyanine derivative tetra-β-(2-(diethylamino)ethoxy) nickel phthalocyanine was synthesized, in two steps, from 4-nitrophthalonitrile and 2-(diethylamino)ethanol, and characterized by mass spectra, 1H nuclear magnetic resonance spectroscopy, ultraviolet visible spectroscopy, infrared spectroscopy and elemental analysis, which confirmed the proposed molecular structure. The inclusion of synthesized phthalocyanine compound in MCM-41 was carried out by the in situ synthesis method using cetyltrimethyl ammonium bromide as structure template and tetraethyl orthosilicate as silica source in presence of this phthalocyanine compound. The inclusion material was studied by means of X-ray diffraction, field emission scanning electron microscopy, high-resolution transmission electron microscopy, nitrogen adsorption isotherm measurements, etc. Results showed that the macromolecular compound was successfully included into MCM-41, the obtained inclusion material displayed mainly prisms and globes, and the material was a kind of mesoporous materials with regularly hexagonal honeycomb array of uniform cylindrical pores and high surface area.

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References

  1. Huang, J., Li, M., Tang, Y., Fang, H., Ding, L.: Copper phthalocyanine catalysis to oxidation of adrenaline by oxygen and its application in adrenaline detection. J. Wuhan Univ. Technol. 23, 606–609 (2008)

    Article  CAS  Google Scholar 

  2. Bilgin, A., Yağci, Ç., Mendi, A., Yildiz, U.: Synthesis and characterization of new metal-free and metallophthalocyanines fused α-methylferrocenylmethoxy units. J. Incl. Phenom. Macrocycl. Chem. 67, 377–383 (2010)

    Article  CAS  Google Scholar 

  3. Sorokin, A.B., Kudrik, E.V.: Phthalocyanine metal complexes: versatile catalysts for selective oxidation and bleaching. Catal. Today 159, 37–46 (2011)

    Article  CAS  Google Scholar 

  4. Pal, M., Ganesan, V.: Zinc phthalocyanine and silver/gold nanoparticles incorporated MCM-41 type materials as electrode modifiers. Langmuir 25, 13264–13272 (2009)

    Article  CAS  Google Scholar 

  5. Sohrabi, H., Esmaeeli, M., Farzaneh, F., Ghandi, M.: Nickel(macrocycle) complexes immobilized within montmorillonite and MCM-41 as catalysts for epoxidation of olefins. J. Incl. Phenom. Macrocycl. Chem. 54, 23–28 (2006)

    Article  CAS  Google Scholar 

  6. Zanjanchi, M.A., Ebrahimian, A., Arvand, M.: Sulphonated cobalt phthalocyanine—MCM-41: an active photocatalyst for degradation of 2,4-dichlorophenol. J. Hazard. Mater. 175, 992–1000 (2010)

    Article  CAS  Google Scholar 

  7. 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 359, 710–712 (1992)

    Article  CAS  Google Scholar 

  8. Trindade, F.J., Rey, J.F.Q., Brochsztain, S.: Covalent attachment of 4-amino-1,8-naphthalimides onto the walls of mesoporous molecular sieves MCM-41 and SBA-15. Dyes Pigm 89, 97–104 (2011)

    Article  CAS  Google Scholar 

  9. Salavati-Niasari, M.: Template synthesis and characterization of cobalt(II) complex nanoparticles entrapped in the zeolite-Y. J. Incl. Phenom. Macrocycl. Chem. 65, 317–327 (2009)

    Article  CAS  Google Scholar 

  10. Hamza, A., Srinivas, D.: Selective oxidation of benzyl alcohol over copper phthalocyanine immobilized on MCM-41. Catal. Lett. 128, 434–442 (2009)

    Article  CAS  Google Scholar 

  11. Li, H.A., van Lier, J.E.: Metal complexes as photo- and radiosensitizers. Chem. Rev. 99, 2379–2450 (1999)

    Article  Google Scholar 

  12. Balkus Jr, K.J., Khamamedova, A., Eissa, M.: Alkane oxidation catalyzed by zeolite encapsulated ruthenium perfluorophthalocyanines. Stud. Surf. Sci. Catal. 97, 189–195 (1995)

    Article  CAS  Google Scholar 

  13. Ma, C., Tian, D., Hou, X., Chang, Y., Cong, F., Yu, H., Du, X., Du, G.: Synthesis and characterization of several soluble tetraphenoxy-substituted copper and zinc phthalocyanines. Synth. Stuttg. 2005, 741–748 (2005)

    Article  Google Scholar 

  14. Cong, F.D., Ning, B., Du, X.G., Ma, C.Y., Yu, H.F., Chen, B.: Facile synthesis, characterization and property comparisons of tetraaminometallophthylocyanines with and without intramolecular hydrogen bonds. Dyes Pigm. 66, 149–154 (2005)

    Article  CAS  Google Scholar 

  15. Huang, W., Liu, B., Sun, F., Zhang, Z., Bao, X.: Synthesis and characterization of thermally stable MCM-41/γ-Al2O3 composite materials. Microporous Mesoporous Mater. 94, 254–260 (2006)

    Article  CAS  Google Scholar 

  16. Bilgin, A., Yağci, Ç., Mendi, A., Yildiz, U.: Synthesis and characterization of new polymeric phthalocyanines substituted with diaza-18-crown-6 macrocycles through ethyleneoxy bridges. Polyhedron 26, 617–625 (2007)

    Article  CAS  Google Scholar 

  17. Kagayama, K., Tamazawa, J., Aida, T.: Extrusion polymerization: catalyzed synthesis of crystalline linear polyethylene nanofibers within a mesoporous silica. Science 285, 2113–2115 (1999)

    Article  Google Scholar 

  18. Shen, S., Guo, L.: Structural, textural and photocatalytic properties of quantum-sized In2S3-sensitized Ti-MCM-41 prepared by ion-exchange and sulfidation methods. J. Solid State Chem. 179, 2629–2635 (2006)

    Article  CAS  Google Scholar 

  19. Gregg, S.J., Sing, K.S.W.: Adsorption, Surface and Porosity, p. 94. Academic Press, New York (1992)

    Google Scholar 

  20. Kruk, M., Jaroniec, M., Sayari, A.: Application of large pore MCM-41 molecular sieves to improve pore size analysis using nitrogen adsorption measurements. Langmuir 13, 6267–6273 (1997)

    Article  CAS  Google Scholar 

  21. Schmidt, R., Hansen, E.W., Stocker, M., Akporiaye, D., Ellestad, O.H.: Pore size determination of MCM-51 mesoporous materials by means of 1H NMR spectroscopy, N2 adsorption, and HREM. A preliminary study. J. Am. Chem. Soc. 117, 4049–4056 (1995)

    Article  CAS  Google Scholar 

  22. Park, S.E., Kim, D.S., Chang, J.S.: Synthesis of MCM-41 using microwave heating with ethylene glycol. Catal. Today 44, 301–308 (1998)

    Article  CAS  Google Scholar 

  23. Prouzet, E., Cot, F., Nabias, G., Larbot, A., Patricia, K., Pinnavaia, T.J.: Assembly of mesoporous silica molecular sieves based on nonionic ethoxylated sorbitan esters as structure directors. Chem. Mater. 11, 1498–1503 (1999)

    Article  CAS  Google Scholar 

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Acknowledgments

We acknowledge financial support of this work by the Foundation for Open Projects of State Key Laboratory of Integrated Optoelectronics (IOSKL-KF200907), Scientific Program of Tianjin City (06TXTJJC14200) and Science Research Development Fund of Tianjin Agricultural University (2008D021).

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Authors and Affiliations

  1. Faculty of Chemistry, Northeast Normal University, Changchun, 130024, China

    Fangdi Cong, Zixiang Cui, Li Li, Junshan Gao & Xiguang Du

  2. Tianjin Key Laboratory of Aqua-ecology and Aquaculture, Tianjin Agricultural University, Tianjin, 300384, China

    Fangdi Cong & Kezhi Xing

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  1. Fangdi Cong
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  2. Zixiang Cui
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  3. Li Li
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  4. Junshan Gao
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  5. Xiguang Du
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Correspondence to Xiguang Du.

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Cong, F., Cui, Z., Li, L. et al. Tetra-β-(2-(diethylamino)ethoxy) nickel phthalocyanine: synthesis and inclusion in MCM-41. J Incl Phenom Macrocycl Chem 71, 225–230 (2011). https://doi.org/10.1007/s10847-011-9934-5

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  • DOI: https://doi.org/10.1007/s10847-011-9934-5

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