Synthesis and characterization of dendritic poly(ether imide)s

Abstract

New dendritic poly(ether imide)s were synthesized by the convergent growth approach, using 1-(4-aminophenyl)-1,1-bis(4-hydroxyphenyl)ethane as the building block. The aromatic nucleophilic substitution of the building block with 3-nitro-N-phenylphthalimide led to the first-generation dendron with aminophenyl group at the focal point, which was subsequently reacted with 3-nitrophthalic anhydride to yield the dendritic wedge containing an activated nitro group; The resulting nitro functionality was allowed to react with the building block to give the second-generation dendron, which was then condensed with 3-nitrophthalic anhydride, followed by ring closure to re-form the phthalimide ring and restore a reactive nitro group. Through an aromatic nucleophilic substitution, the dendritic wedges with an activated nitro group were coupled to the polyfunctional core to form the dendritic macromolecules. Structures of the ether-imide dendrimers were fully characterized by use of a combination of techniques including H-1 NMR, C-13 NMR, IR, and mass spectrometry. The glass transition temperature of the dendrimers increased with molecular weight, and the variation was consistent with theoretical calculations. These dendritic poly(ether imide)s are soluble in various organic solvents and had a thermal stability comparable to linear poly(aryl ether imide)s.