Novel poly(pyridine imide) with pendent naphthalene groups: Synthesis and thermal,optical, electrochemical,electrochromic, and protonation characterization |
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Authors: | Der-Jang Liaw Kun-Li Wang Feng-Chyuan Chang Kueir-Rarn Lee Juin-Yih Lai |
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Institution: | 1. Department of Chemical Engineering, National Taipei University of Science and Technology, Taipei 106, Taiwan, Republic of China;2. Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei 106, Taiwan, Republic of China;3. R&D Center for Membrane Technology, Chung-Yuan Christian University, Chung-Li 32023, Taiwan, Republic of China |
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Abstract: | A new diamine containing a pyridine heterocyclic group and a naphthalene substituent, 4-(2-naphthyl)-2,6-bis(4-aminophenyl) pyridine (NBAPP), was synthesized with the Chichibabin reaction and used in the preparation of poly(pyridine imide) by direct polycondensation with 4,4′-hexafluoroisopropylidenediphathalic anhydride in N-methyl-2-pyrrolidinone (NMP). The poly(pyridine imide) derived from diamine NBAPP with naphthalene substituents was highly organosoluble: it was soluble in tetrahydrofuran, NMP, N,N-dimethylacetamide (DMAc), N,N-dimethylformamide, and γ-butyrolactone at room temperature and in pyridine, dimethyl sulfoxide, and cyclohexanone upon heating at 70 °C. The poly(pyridine imide) was converted into lightly colored, optically transparent, flexible, and tough polyimide films via casting onto glass from a DMAc solution. This polymer exhibited good thermal stability (temperature of 10% weight loss = 527 °C) in air and high dielectric constants (as high as 4.20 at 1 kHz). The polyimide films had a tensile strength of 102 MPa and a tensile modulus of 1.8 GPa. As for the optical properties, the polymer exhibited UV–vis absorption bands in the region of 223–450 nm and possessed strong green-yellow fluorescence (500 nm) after being protonated with acid. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 2367–2374, 2007 |
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Keywords: | electrochemistry polyimides protonation |
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