New fluorinated poly(pyridine amide)s derived from 2, 6-bis(4-iodophenyl)-4-(4-trifluoromethylphenyl)pyridine by C–N coupling reaction. (October 2022)

• Record Type: Journal Article
• Authors: Xie, Hui; Zhao, Jing-Wei; Wei, Mei-Hong; Huang, Zhi-Hui; Liu, Xiao-Ling
• Is Part Of: High performance polymers. Volume 34:Number 8(2022)
• Page Start: 952
• Page End: 962
• Publication Date: 2022-10
• Subjects: Aromatic fluorinated poly(pyridine amide)s -- 2, 6-diphenyl-4-(4-trifluoromethylphenyl)pyridine units -- 2, 6-bis(4-iodophenyl)-4-(4-trifluoromethylphenyl)pyridine -- palladium-catalyzed carbonylation polycondensation -- carbon monoxide -- synthesis -- characterization; Polymerization -- Periodicals; Polymers -- Periodicals; 547.7
• DOI: 10.1177/09540083221095760
• Languages: English
• ISSNs: 0954-0083

Abstract

2, 6-Bis(4-iodophenyl)-4-(4-trifluoromethylphenyl)pyridine, as a new aromatic diiodide compound, was synthesized through a one-pot protocol by the sequential diazotization-iodination of 2, 6-bis(4-aminophenyl)-4-(4-trifluoromethylphenyl)pyridine with KI/NaNO2 / p -TsOH in acetonitrile at room temperature. A number of new aromatic fluorinated poly(pyridine amide)s containing 2, 6-diphenyl-4-(4-trifluoromethylphenyl)pyridine units were prepared via a Pd(PPh3 )2 Cl2 catalyzed carbonylation polymerization of this diiodide, diamines and carbon monoxide in DMAc in the presence of PPh3 and 1, 8-diazabicyclo[5, 4, 0]-7-undecene. These new polyamides with inherent viscosities of 0.63–0.72 dL/g were amorphous and easily soluble in amide type aprotic solvents such as NMP, DMAc, DMF and dimethyl sulfoxide at room temperature. Thermal analysis data up to 800°C in nitrogen showed their high thermal behavior with 5% weight loss temperature of 428–498°C and char yield of 62–69%. Their limiting oxygen index of 42.3–45.1 showed that the resulting poly(pyridine amide)s could be classified as "self-extinguishing polymers". Also, their thin films exhibited high optical transparency with a cut-off wavelength of 324–373 nm.