Monofunctional Aminophenyl Polyhedral Oligomeric Silsesquioxanes - A Model for High Performance Nanocomposite Monomers

doi:https://doi.org/10.21236/ada411127

Monofunctional Aminophenyl Polyhedral Oligomeric Silsesquioxanes - A Model for High Performance Nanocomposite Monomers

Rene I. Gonzalez,Brent D. Viers,Timothy S. Haddad-2002-03-26

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Abstract : An aminophenyl functionalized polyhedral silsesquioxane (POSS) was synthesized as a model monofunctional organic-inorganic hybrid monomer. A multistep procedure whereby an incompletely condensed POSS triol scaffold was corner capped with phenyltrichlorosilane and then the phenyl moiety was nitrated and subsequently reduced with Zn/HCl to form the desired aminophenylPOSS (POSS aniline). Mononitration and quantitative reduction to a monoamine was observed. Furthermore, the amine was isolated as the free base, and not as a salt. However, 1H COSY NMR spectroscopy indicates that a variety of POSS aniline isomers are formed, ortho disubstitution most prevalent (57%), with meta (38%), and para (5%).

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Abstract : An aminophenyl functionalized polyhedral silsesquioxane (POSS) was synthesized as a model monofunctional organic-inorganic hybrid monomer. A multistep procedure whereby an incompletely condensed POSS triol scaffold was corner capped with phenyltrichlorosilane and then the phenyl moiety was nitrated and subsequently reduced with Zn/HCl to form the desired aminophenylPOSS (POSS aniline). Mononitration and quantitative reduction to a monoamine was observed. Furthermore, the amine was isolated as the free base, and not as a salt. However, 1H COSY NMR spectroscopy indicates that a variety of POSS aniline isomers are formed, ortho disubstitution most prevalent (57%), with meta (38%), and para (5%).

Keywords

MonomerNanocompositeSilsesquioxanePolymer chemistryMaterials scienceChemical engineeringChemistryPolymer science

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