Abstract
The bromination and characterization of octaphenylsilsesquioxane is reported. The reaction is successful with a variety of methods, including microwave assisted synthesis. The analysis of the obtained product mix was carried out with a combination of high performance liquid chromatography and matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS). The analysis indicates that the bromination leads to multiple bromines per octaphenylsilsesquioxane molecule with a distribution dominated by statistical odds and the reaction conditions. The results showed that the bromination is not selective and does not lead to a single defined product.
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Abbreviations
- MALDI-TOF-MS:
-
matrix assisted laser desorption ionization time-of-flight mass spectra
- POSS:
-
polyhedral oligomeric silsesquioxane
- OPS:
-
octaphenylsilsesquioxane
References
Harrison, P.G. 1997, J. Organometallic Chemistry 542, 141–183.
Sellinger, A. & Laine, R.M. 1996, Macromolecules 29, 2327–2330.
Sellinger, A. & Laine, R.M. 1996, Chem. Mater. 8, 1592–1593.
Zhang, C., Babonneau, F., Bonhomme, C., Laine, R.M., Soles, C.L., Hristov, H.A., Yee, & A.F. 1998, J. Am. Chem. Soc. 120, 8380–8391.
Choi, J., Kim, S.G., & Laine, R.M. 2004, Macromolecules 37, 99–109.
Schwab, J.J. & Lichtenhan, J.D. 1998, Appl. Organomet. Chem. 12, 707.
Laine, R.M., Tamaki, R., & Choi, J. 2005, U. S. Patent 6,927,301 B2.
Su, R. Q., Müller, T.E., Procházka, J., & Lercher, J.A. 2002, Adv. Mater. 14(19), 1369–1373.
Tegou, E., Bellas, V., Gogolides, E., Argitis, P., Eon, D., Cartry, G., & Cardinaud, C. 2004, Chem. Mater. 16, 2567–2577.
Feher, F.J. & Wyndham, K.D. 1998, Chem. Commun. 323–324.
Voronkov, M.G. & Lavrent'ev, V. 1982, Top. Curr. Chem. 102, 199.
Feher, F.J. & Budzichowski, T.A. 1989, J. Organometallic Chem. 379, 33–40.
Bassindale, A.R., Liu, Z., MacKinnon, I.A., Taylor, P.G., Yang, Y., Light, M.E., Horton, P.N., & Hursthouse, M. B. 2003, Dalton Trans. 2945–2949.
Sprung, M.M. & Guenther, F.O. 1955, J. Am. Chem. Soc. 77, 3996–4002.
Sprung, M.M. & Guenther, F.O. 1955, J. Am. Chem. Soc. 77, 6045–6047.
Scott, D.W. 1946, J. Am. Chem. Soc. 68, 356–359.
Olsson, K. & Grönwall, C. 1966, Arkiv for Kemi 17(54), 529–540.
Brown, J.F., Jr., Vogt, L.H., Jr., & Prescott, P.I. 1964, J. Am. Chem. Soc. 86, 1120–1125.
Brown, J.F., Jr. & Vogt, L.H., Jr. 1965, J. Am. Chem. Soc. 87(19), 4313–4317.
(a) He, C., Xiao, Y., Huang, J., Lin, T., Mya, K.Y., & Zhang, X. 2004, J. Am. Chem. Soc. 126, 7792–7793; (b) It has been pointed out during the review of this article that the Suzuki coupling, not recommended by He et al., is a viable synthetic method for polyaromatic octasilsesquioxane (see ref. [22]).
Suppliers include Aldrich, HybridPlastics and Mayaterials. Octabromophenyl-octasilsesquioxane is available from Mayaterials.
Brick, C.M., Ouchi, Y., Chujo, Y., & Laine, R.M. 2005, Macromolecules 38, 4661–4665.
Brick, C.M., Tamaki, R., Kim, S.-G., Asuncion, M.Z., Roll, M., Nemoto, T., Ouchi, Y., Chujo, Y., & Laine, R.M. 2005, Macromolecules 38, 4655–4660.
Militzer, W. 1938, J. Am. Chem. Soc. 60(2), 256–257.
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Erben, C., Grade, H. & Goddard, G.D. Bromination of octaphenylsilsesquioxane. Silicon Chem 3, 43–49 (2006). https://doi.org/10.1007/s11201-005-9000-5
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DOI: https://doi.org/10.1007/s11201-005-9000-5