Affiliation:
1. State Key Laboratory of Fine Chemicals, Carbon Research Laboratory, School of Chemical Engineering, Dalian University of Technology, Dalian, China
2. School of Chemical Engineering, University of Science and Technology Liaoning, Gaoxin District, Anshan, Liaoning, China
Abstract
The aromatic diamine monomer containing a pyridine heterocyclic group and a tert-butyl substituent, 4-[(4′- tert-butyl)phenyl]-2,6-bis(4-aminophenyl)pyridine (BPAP), was successfully synthesized by a modified Chichibabin reaction of 4-nitro-acetophenone and 4- tert-butyl benzaldehyde, followed by a reduction of the resulting dinitro compound 4-[(4′- tert-butyl)phenyl]-2,6-bis(4-nitrophenyl)pyridine with palladium/carbon and hydrazine monohydrate, successively. A series of poly(pyridine–imide)s were prepared from the diamine BPAP with the alicyclic anhydride 1,2,3,4-cyclobutanetetracarboxylic dianhydride, aromatic anhydride pyromelitic dianhydride, 3,3′,4,4′-biphenyl tetracarboxylic dianhydride, and 4,4′-oxydiphthalic anhydride in N, N-dimethylformamide (DMF) via the conventional two-step method and further chemical imidization to obtain poly(pyridine-imide) powders. Due to the introduction of tert-butyl group, the polyimides (PIs) derived from BPAP were amorphous and displayed good solubility in amine-type polar solvents, such as DMF, dimethyl sulfoxide, N, N-dimethylacetamide, and N-methyl-2-pyrrolidone. Because of the presence of rigid triphenylpyridine units and bulky substituents, the final PIs held a good thermal stability with 10% weight loss temperatures above 504°C and left more than 55% residue even at 700°C under nitrogen atmosphere. The effect of tert-butyl substituents on the properties of the PIs was studied by comparing with 4-phenyl-2,6-bis(4-nitrophenyl)pyridine. These PIs exhibited some fluorescent properties because of the triphenylpyridine units, and the chemical structure of dianhydrides took an effect on the fluorescent property of these PIs.
Subject
Materials Chemistry,Organic Chemistry,Polymers and Plastics
Cited by
3 articles.
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