Methyl methacrylate polymerization at samarium(II)-grafted MCM-41

Tetrahedron

Volumn 59, Issue 52, 2003, Pages 10567-10574

  Anwander, Reiner ^a   Nagl, Iris ^a   Zapilko, Clemens ^a   Widenmeyer, Markus ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alkoxide ligand; Alkyl ligand; Indenyl ligand; Mesoporous silica MCM 41; Methyl methacrylate (MMA); Organoaluminum reagents; Polymerization; Samarium(II); Surface organometallic chemistry (SOMC)

Indexed keywords

MCM 41; METHACRYLIC ACID METHYL ESTER; SAMARIUM; SILICON DIOXIDE;

ARTICLE; CHEMICAL REACTION; FOURIER ANALYSIS; INFRARED SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SCANNING ELECTRON MICROSCOPY; SYNTHESIS;

EID: 0348050012     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.07.018     Document Type: Article

References (57)

1. (a) Molander G.A., Harris C.R. Chem. Rev. 96:1996;307-338
2. (b) Kagan H.B., Namy J.-L. Top. Organomet. Chem. 2:1999;155-198.
3. (a) Narita M., Nomura R., Tomita I., Endo T. Macromolecules. 31:1998;2774-2778
4. (b) Gosho A., Nomura R., Tomita I., Endo T. Macromolecules. 31:1998;3388-3390
5. (c) Tanaka M., Sudo A., Sanda F., Endo F. Chem. Commun. 2000;2503-2504.
6. For reviews, see: (a) Yasuda H. Top. Organomet. Chem. 2:1999;255-283 (b) Anwander R. Cornils B., Herrmann W.A. Applied Homogeneous Catalysis with Organometallic Compounds. Vol. 2:2002;974-1014 VCH, Weinheim, (c) Hou Z., Wakatsuki Y. Coord. Chem. Rev. 231:2002;1-22.
7. For reviews, see: (a) Yasuda H. Top. Organomet. Chem. 2:1999;255-283 (b) Anwander R. Cornils B., Herrmann W.A. Applied Homogeneous Catalysis with Organometallic Compounds. Vol. 2:2002;974-1014 VCH, Weinheim, (c) Hou Z., Wakatsuki Y. Coord. Chem. Rev. 231:2002;1-22.
8. For reviews, see: (a) Yasuda H. Top. Organomet. Chem. 2:1999;255-283 (b) Anwander R. Cornils B., Herrmann W.A. Applied Homogeneous Catalysis with Organometallic Compounds. Vol. 2:2002;974-1014 VCH, Weinheim, (c) Hou Z., Wakatsuki Y. Coord. Chem. Rev. 231:2002;1-22.
9. (a) Boffa L.S., Novak B.M. Macromolecules. 27:1994;6993-6995
10. (b) Boffa L.S., Novak B.M. Tetrahedron. 53:1997;15367-15396.
11. Nodono M., Tokimitsu T., Makino T. Macromol. Chem. Phys. 204:2003;877-884.
12. Ihara E., Koyama K., Yasuda H., Kanehisa N., Kai Y. J. Organomet. Chem. 574:1999;40-49.
13. (a) Boven G., Oosterling M.L.C.M., Challa G., Schouten A.J. Polymer. 31:1990;2377-2383
14. (b) Matsuda T., Saito N., Sugawara T. Macromolecules. 29:1996;7446-7451
15. (c) Ejaz M., Yamamoto S., Ohno K., Tsujii Y., Fukuda T. Macromolecules. 31:1998;5934-5936
16. (d) Zhao B., Brittain W.J. J. Am. Chem. Soc. 121:1999;3557-3558
17. (e) Ingall M.D.K., Joray S.J., Duffy D.J., Long D.P., Bianconi P.A. J. Am. Chem. Soc. 122:2000;7845-7846.
18. Nagl I., Widenmeyer M., Grasser S., Köhler K., Anwander R. J. Am. Chem. Soc. 122:2000;1544-1545.
19. Miyata M. Reinhoudt D.N. Comprehensive Supramolecular Chemistry. Vol. 10:1996;557-582 Pergamon, Oxford.
20. Tajima K., Aida T. Chem. Commun. 2000;2399-2412.
21. Anwander R. Chem. Mater. 13:2001;4419-4438.
22. For, PMMA-PMS composite materials obtained via free radical polymerization (T70°C), see: (a) Llewellyn P.L., Ciesla U., Becher H., Stadler R., Schüth F., Unger K.K. Stud. Surf. Sci. Catal. 84: 1994;2013-2020 (b) Ng S.M., Ogino S., Aida T. Macromol. Rapid Commun. 18:1997;991-996 (c) Möller K., Bein T., Fischer R.X. Chem. Mater. 10:1998;1841-1852 (d) Möller K., Bein T., Fischer R.X. Chem. Mater. 11:1999;665-673.
23. For, PMMA-PMS composite materials obtained via free radical polymerization (T70°C), see: (a) Llewellyn P.L., Ciesla U., Becher H., Stadler R., Schüth F., Unger K.K. Stud. Surf. Sci. Catal. 84: 1994;2013-2020 (b) Ng S.M., Ogino S., Aida T. Macromol. Rapid Commun. 18:1997;991-996 (c) Möller K., Bein T., Fischer R.X. Chem. Mater. 10:1998;1841-1852 (d) Möller K., Bein T., Fischer R.X. Chem. Mater. 11:1999;665-673.
24. For, PMMA-PMS composite materials obtained via free radical polymerization (T70°C), see: (a) Llewellyn P.L., Ciesla U., Becher H., Stadler R., Schüth F., Unger K.K. Stud. Surf. Sci. Catal. 84: 1994;2013-2020 (b) Ng S.M., Ogino S., Aida T. Macromol. Rapid Commun. 18:1997;991-996 (c) Möller K., Bein T., Fischer R.X. Chem. Mater. 10:1998;1841-1852 (d) Möller K., Bein T., Fischer R.X. Chem. Mater. 11:1999;665-673.
25. For, PMMA-PMS composite materials obtained via free radical polymerization (T70°C), see: (a) Llewellyn P.L., Ciesla U., Becher H., Stadler R., Schüth F., Unger K.K. Stud. Surf. Sci. Catal. 84: 1994;2013-2020 (b) Ng S.M., Ogino S., Aida T. Macromol. Rapid Commun. 18:1997;991-996 (c) Möller K., Bein T., Fischer R.X. Chem. Mater. 10:1998;1841-1852 (d) Möller K., Bein T., Fischer R.X. Chem. Mater. 11:1999;665-673.
26. Kageyama K., Ogino S., Aida T., Tatsumi T. Macromolecules. 31:1998;4069-4073.
27. Abdel-Fattah T.M., Pinnavaia T.J. Chem. Commun. 1996;665-666.
28. Ko Y.S., Han T.K., Park J.W., Woo S.I. Macromol. Rapid Commun. 17:1996;749-758.
29. (a) Tudor J., O'Hare D. Chem. Commun. 1997;603-604
30. (b) O'Brien S., Tudor J., Maschmeyer T., O'Hare D. Chem. Commun. 1997;1905-1906.
31. (a) Van Looveren L.K., Geysen D.F.M.C., Vercruysse K.A.L., Wouters B.H.J., Grobet P.J., Jacobs P.A. Angew. Chem. 110:1998;540-543. Angew. Chem., Int. Ed. 1998, 37, 517-520
32. (b) Van Looveren L.K., Geysen D.F.M.C., Vercruysse K.A.L., Wouters B.H.J., Grobet P.J., Jacobs P.A. Stud. Surf. Sci. Catal. 117:1998;477-484.
33. Sano T., Doi K., Hagimoto H., Wang Z., Uozumi T., Soga K. Chem. Commun. 1999;733-734.
34. Rahiala H., Beurroies I., Eklund T., Hakala K., Gougeon R., Trens P., Rosenholm J.B. J. Catal. 188:1999;14-23.
35. Lee K.-S., Oh C.-G., Yim J.-H., Ihm S.-K. J. Mol. Catal. 159:2000;301-308.
36. (a) Kageyama K., Tamazawa J., Aida T. Science. 285:1999;2113-2115
37. (b) Tajima K., Ogawa G., Aida T. J. Polym. Sci. A: Polym. Chem. 38:2000;4821-4825.
38. (a) Rao R.R., Weckhuysen B.M., Schoonheydt R.A. Chem. Commun. 1999;445-446
39. (b) Weckhuysen B.M., Rao R.R., Pelgrims J., Schoonheydt R.A., Bodart P., Debras G., Collart O., Van Der Voort P., Vansant E.F. Chem. Eur. J. 6:2000;2960-2970.
40. Anwander R., Nagl I., Widenmeyer M., Engelhardt G., Groeger O., Palm C., Röser T. J. Phys. Chem. B. 104:2000;3532-3544.
41. Anwander R. Top. Organomet. Chem. 2:1999;1-61.
42. Anwander R., Palm C. Stud. Surf. Sci. Catal. 117:1998;413-420.
43. For use of this indenyl ligand in homogeneously performed silylamine elimination reactions, see: Klimpel M.G., Herrmann W.A., Anwander R. Organometallics. 19:2000;4666-4668.
44. Klimpel M.G., Anwander R., Tafipolsky M., Scherer W. Organometallics. 20:2001;3983-3992.
45. Nagl I., Widenmeyer M., Herdtweck E., Raudaschl-Sieber G., Anwander R. Microporous Mesoporous Mater. 44-45:2001;311-319.
46. (a) Jenkner H. Z. Naturforsch. 14B:1959;133
47. (b) Mehrotra R.C., Rai A.K. Polyhedron. 10:1991;1967
48. (c) Feher F.J., Budzichowski T.A., Weller K.J. Polyhedron. 12:1993;591.
49. Sing K.S.W., Everett D.H., Haul R.A.W., Moscou L., Pierotti R.A., Rouquérol J., Siemieniewska T. Pure Appl. Chem. 57:1985;603-619.
50. Jaroniec C.P., Kruk M., Jaroniec M., Sayari A. J. Phys. Chem. B. 102:1998;5503.
51. 3-alkylated Sc(III)-grafted MCM-41 reported in Ref. 28 produced 1.693 g PMMA per 1 g of MCM-41.
52. (a) Anwander, R.; Nagl, I.; Hölemann, A.; Reißig, H.-U. Unpublished results. (b) Nagl, I. Ph.D. Thesis, Technische Universität München, 2002.
53. Grubbs R.H., Pangborn A.B., Giardello M.A., Rosen R.K., Timmers F.J. Organometallics. 15:1996;1518-1520.
54. The mesoporous silicas were synthesized according to slightly modified literature procedures, pore-expanded materials were employed better to apply the BJH pore size analysis to the Sm(II) hybrid materials. Mesitylene was used as a swelling reagent for the preparation of pore-expanded MCM-41 ( 1 ): (a) 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. J. Am. Chem. Soc. 114:1992;10834-10843 (b) Widenmeyer, M. Ph.D. Thesis, Technische Universität München, 2001.
55. Nagl I., Scherer W., Tafipolsky M., Anwander R. Eur. J. Inorg. Chem. 1999;1405-1407.
56. Eppinger J., Spiegler M., Hieringer W., Herrmann W.A., Anwander R. J. Am. Chem. Soc. 122:2000;3080-3096.
57. Allen R.D., Long T.E., McGrath J.E. Polym. Bull. 15:1986;127.