Synthesis of perylene dianhydride-incorporated main chain polyimides and sequential structural transformation through a dipolar cycloaddition |
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| Affiliation: | 1. Department of Applied Materials and Optoelectronic Engineering, National Chi Nan University, Puli, Nantou, Taiwan;2. Department of Electric Engineering, Tunghai University, Taichung, Taiwan;3. Department of Electrical Engineering, National Chi Nan University, Puli, Nantou, Taiwan;1. Advanced Functional Polymers Research Center, Korea Research Institute of Chemical Technology, 141 Gajeong-ro, Yuseong-gu, Daejeon, 34114, South Korea;2. Thin Film Materials Research Center, Korea Research Institute of Chemical Technology, 141 Gajeong-ro, Yuseong-gu, Daejeon, 34114, South Korea;3. Silicon Photonics Research Section, Electronics and Telecommunications Research Institute, 218 Gajeong-ro, Yuseong-gu, Daejeon, 34129, South Korea;1. School of Chemical, Biological and Materials Engineering, University of Oklahoma, 100 E. Boyd Street, Norman 73019, OK, USA;2. Department of Chemical, Materials and Industrial Production Engineering, University of Naples Federico II, p.le Tecchio 80, 80125 Naples, Italy;3. Department of Chemical and Biomolecular Engineering, University of Notre Dame, 205 McCourtney Hall, Notre Dame 46556, IN, USA;1. Department of Physical Chemistry, University of Chemistry and Technology Prague, Technická 5, Prague 6, 166 28, Czech Republic;2. Department of Polymers, University of Chemistry and Technology Prague, Technická 5, Prague 6, 166 28, Czech Republic;3. Department of Chemical Engineering, University of Chemistry and Technology Prague, Technická 5, Prague 6, 166 28, Czech Republic;4. Department of Inorganic Technology, Technická 5, University of Chemistry and Technology Prague, Prague 6, 166 28, Czech Republic;5. Department of Biochemistry and Microbiology, Technická 5, University of Chemistry and Technology Prague, Prague 6, 166 28, Czech Republic |
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| Abstract: | Perylene dianhydride (PDA)-incorporated polyimides were prepared. The perylene unit in the polyimide was thermally converted to the corresponding N-heterocyclic polyarene unit through a Diels–Alder reaction. The monomer, 2,2-bis(3-amino-4-hydroxyphenyl) hexafluoropropane (6FAP), was modified via O-alkylation to improve the solubility of the polymer. 2-Ethylhexyl-attached 6FAP yielded a soluble copolyimide that contained ca. 70 mol% PDA using pyromellitic dianhydride. The perylene unit of the copolyimide transformed to a polyarene unit through the dipolar cycloaddition of 4-aryl-1,2,4-triazole-3,5-dione (TAD) and maleic anhydride. The perylene transformation of the polyimide occurred with 50% conversion with maleic anhydride and quantitatively with TAD. The PDA-copolymer exhibited a spectral blue-shift and red-shift by maleic anhydride and TAD, respectively. |
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| Keywords: | Perylene polymer Dipolar cycloaddition 1,2,4-Triazole-3,5-dione Aromatic copolyimide NIR absorption |
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