Topics in Catalysis

, Volume 53, Issue 3–4, pp 187–191

Urea and Thiourea-Functionalized Mesoporous Silica Nanoparticle Catalysts with Enhanced Catalytic Activity for Diels–Alder Reaction

  • Hung-Ting Chen
  • Brian G. Trewyn
  • Jerzy W. Wiench
  • Marek Pruski
  • Victor S.-Y. Lin
Original Paper


A series of urea- and thiourea-functionalized mesoporous silica nanoparticles (MSN) was synthesized. These materials exhibited a superior catalytic reactivity for Diels–Alder reaction than their homogeneous analogues. The reactivity enhancement was attributed to the site isolation effect induced by the heterogenization of individual catalytic group. The surface hydrogen bonding between the organic catalysts and silanols also improved the catalytic reactivity.


Thiourea Mesoporous silica nanoparticle Heterogeneous catalysis Surface hydrogen bonding Diels–Alder reaction 


  1. 1.
    Corma A (1997) Chem Rev 97:2373–2419CrossRefGoogle Scholar
  2. 2.
    Lim MH, Stein A (1999) Chem Mater 11:3285–3295CrossRefGoogle Scholar
  3. 3.
    Stein A (2003) Adv Mater 15:763–775CrossRefGoogle Scholar
  4. 4.
    Stein A, Melde BJ, Schroden RC (2000) Adv Mater 12:1403–1419CrossRefGoogle Scholar
  5. 5.
    De Juan F, Ruiz-Hitzky E (2000) Adv Mater 12:430–432CrossRefGoogle Scholar
  6. 6.
    Johnson BFG, Raynor SA, Shephard DS, Mashmeyer T, Mashmeyer T, Thomas JM, Sankar G, Bromley S, Oldroyd R, Gladden L, Mantle MD (1999) Chem Commun 1167–1168Google Scholar
  7. 7.
    Mal NK, Fujiwara M, Tanaka Y (2003) Nature 421:350–353CrossRefGoogle Scholar
  8. 8.
    Jones CW, McKittrick MW, Nguyen JV, Yu K (2005) Top Catal 34:67–76CrossRefGoogle Scholar
  9. 9.
    McKittrick MW, Jones CW (2003) Chem Mater 15:1132–1139CrossRefGoogle Scholar
  10. 10.
    Cassiers K, Linssen T, Mathieu M, Benjelloun M, Schrijnemakers K, Van Der Voort P, Cool P, Vansant EF (2002) Chem Mater 14:2317–2324CrossRefGoogle Scholar
  11. 11.
    Igarashi N, Hashimoto K, Tatsumi T (2002) J Mater Chem 12:3631–3636CrossRefGoogle Scholar
  12. 12.
    Igarashi N, Koyano KA, Tanaka Y, Nakata S, Hashimoto K, Tatsumi T (2003) Microporous Mesoporous Mater 59:43–52CrossRefGoogle Scholar
  13. 13.
    Kruk M, Jaroniec M, Sayari A (1999) Microporous Mesoporous Mater 27:217–229CrossRefGoogle Scholar
  14. 14.
    Kumar R, Chen H-T, Escoto JLV, Lin VSY, Pruski M (2006) Chem Mater 18:4319–4327CrossRefGoogle Scholar
  15. 15.
    Caravajal GS, Leyden DE, Quinting GR, Maciel GE (1988) Anal Chem 60:1776–1786CrossRefGoogle Scholar
  16. 16.
    Kanan SM, Tze WTY, Tripp CP (2002) Langmuir 18:6623–6627CrossRefGoogle Scholar
  17. 17.
    McKittrick MW, Jones CW (2004) J Am Chem Soc 126:3052–3053CrossRefGoogle Scholar
  18. 18.
    Bass JD, Solovyov A, Pascall AJ, Katz A (2006) J Am Chem Soc 128:3737–3747CrossRefGoogle Scholar
  19. 19.
    Defreese JL, Hwang S-J, Parra-Vasquez ANG, Katz A (2006) J Am Chem Soc 128:5687–5694CrossRefGoogle Scholar
  20. 20.
    Notestein JM, Iglesia E, Katz A (2004) J Am Chem Soc 126:16478–16486CrossRefGoogle Scholar
  21. 21.
    Notestein JM, Katz A (2006) Chem Eur J 12:3954–3965CrossRefGoogle Scholar
  22. 22.
    Dalko PI, Moisan L (2001) Angew Chem Int Ed 40:3726–3748CrossRefGoogle Scholar
  23. 23.
    McCooey SH, Connon SJ (2005) Angew Chem Int Ed 44:6367–6370CrossRefGoogle Scholar
  24. 24.
    Okino T, Hoashi Y, Takemoto Y (2003) J Am Chem Soc 125:12672–12673CrossRefGoogle Scholar
  25. 25.
    Okino T, Hoashi Y, Takemoto Y (2003) Tetrahedron Lett 44:2817–2821CrossRefGoogle Scholar
  26. 26.
    Schreiner PR (2003) Chem Soc Rev 32:289–296CrossRefGoogle Scholar
  27. 27.
    Schreiner PR, Wittkopp A (2002) Org Lett 4:217–220CrossRefGoogle Scholar
  28. 28.
    Schuster T, Bauch M, Duerner G, Goebel MW (2000) Org Lett 2:179–181CrossRefGoogle Scholar
  29. 29.
    Taylor MS, Jacobsen EN (2006) Angew Chem Int Ed 45:1520–1543CrossRefGoogle Scholar
  30. 30.
    Wittkopp A, Schreiner PR (2003) Chem Eur J 9:407–414CrossRefGoogle Scholar
  31. 31.
    Chen H-T, Huh S, Wiench JW, Pruski M, Lin VSY (2005) J Am Chem Soc 127:13305–13311CrossRefGoogle Scholar
  32. 32.
    Huh S, Chen H-T, Wiench JW, Pruski M, Lin VSY (2004) J Am Chem Soc 126:1010–1011CrossRefGoogle Scholar
  33. 33.
    Huh S, Chen H-T, Wiench JW, Pruski M, Lin VSY (2005) Angew Chem Int Ed 44:1826–1830CrossRefGoogle Scholar
  34. 34.
    Huh S, Wiench JW, Trewyn BG, Song S, Pruski M, Lin VSY (2003) Chem Commun 2364–2365Google Scholar
  35. 35.
    Huh S, Wiench JW, Yoo J-C, Pruski M, Lin VSY (2003) Chem Mater 15:4247–4256CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Hung-Ting Chen
    • 1
    • 2
  • Brian G. Trewyn
    • 1
  • Jerzy W. Wiench
    • 2
  • Marek Pruski
    • 1
    • 2
  • Victor S.-Y. Lin
    • 1
    • 2
  1. 1.Department of ChemistryIowa State UniversityAmesUSA
  2. 2.U.S. Department of Energy Ames LaboratoryIowa State UniversityAmesUSA

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