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Synthesis of well‐defined poly(<i>p</i>‐benzamide) from chain‐growth polycondensation and its application to block copolymers
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2003
Year
Macromolecular ChemistryEngineeringLow PolydispersityResponsive PolymersOrganic ChemistryChemistryMolecular PolymerPolymersPolymer MaterialMacromolecular EngineeringPolymer ChemistryMaterials SciencePolymer EngineeringBiopolymersBiomolecular EngineeringBlock Co-polymersPolymer ScienceAmide LinkagePolymer CharacterizationChain‐growth PolycondensationAbstract PolyPolymer ReactionPolymer Synthesis
Abstract Poly( p ‐benzamide) with a defined molecular weight and a low polydispersity and block copolymers containing this well‐defined aramide was synthesized. Phenyl 4‐(4‐octyloxybenzylamino)benzoate ( 1b ) polymerized at room temperature in the presence of base and phenyl 4‐nitrobenzoate ( 2a ) as an initiator in a chain‐growth polycondensation manner to give well‐defined aromatic polyamides having the 4‐octyloxybenzyl groups as a protecting group on nitrogen in an amide. It was confirmed by a model reaction that deprotection of this protecting group proceeded completely with trifluoroacetic acid (TFA) without breaking the amide linkage. The utility of this approach to poly( p ‐benzamide) with a low polydispersity was demonstrated by the synthesis of block copolymers of poly( p ‐benzamide) and poly( N ‐octyl‐ p ‐benzamide) or poly(ethylene glycol). The SEM images of the supramolecular assemblies of the former block copolymer showed μm‐sized bundles and aggregates of flake structures.