Synthesis and properties of polybenzazoles containing
flexible methylene in backbone
XU Xiaohui, LIU Xiaoyun, ZHOU Chengjun, ZHUANG Qixin, HAN Zhewen
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Key Laboratory for Ultrafine Materials of Education, School of Materials Science and Engineering, East China University of Science and Technology;
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Published
05 Dec 2008
Issue Date
05 Dec 2008
Abstract
A novel series of polybenzazoles with rigid-rod benzoxazole cycle and soft methylene segment was designed and synthesized via solution condensation polymerizations from 4,6-diamino-1,3-benzenediol diphosphate, terephthalic acid and aliphatic dicarboxylic acid. The structures of polybenzazoles were characterized by means of FT-IR, 1H NMR and Wide-angle X-ray diffraction (WAXRD). All the polymers show excellent thermal stability and the Tds was above 471°C. The intrinsic viscosities [?] of the polymers ranged from 0.8 to 0.9. The UV-Vis absorption peaks of the polymers in MSA were blue-shifted from 429 nm for PBO to 291 nm for PBOC7, and the Stokes shifts in PL spectra enlarged.
XU Xiaohui, LIU Xiaoyun, ZHOU Chengjun, ZHUANG Qixin, HAN Zhewen.
Synthesis and properties of polybenzazoles containing
flexible methylene in backbone. Front. Chem. Sci. Eng., 2008, 2(4): 412‒416 https://doi.org/10.1007/s11705-008-0073-5
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References
1. Ulrich D R . Multifunctional macromolecular ultrastructures: introductorycomments speciality polymers. Polymer, 1987, 28: 533–542. doi:10.1016/0032-3861(87)90466-6 2. Kitagawa T, Yabuki K, Young R J . An investigation into the relationshipbetween processing, structure and properties for high-modulus PBOfibres. Part 1: raman band shifts and broadeningin tension and compression, 2001, 42: 2101–2112 3. So Y H, Zaleski J M, Murlick C, Ellaboudy A . Synthesis and photophysical properties of some benzoxazoleand benzothiazole compounds. Macromolecules, 1996, 29: 2783–2795. doi:10.1021/ma951431i 4. Wang S, Wu P, Han Z . Photophysical properties of lyotropic liquid crystallinepolybenzazoles and evidence of aggregate formation for polybenzazolesin methanesulfonic acid. Macromolecules, 2003, 36: 4567–4576.. doi: 10.1021/ma0300600 5. Alam M M, Jenekhe S A . Polybenzobisazoles are efficient electron transport materials forimproving the performance and stability of polymer light-emittingdiodes. Chem Mater, 2002, 14: 4775–4780. doi:10.1021/cm020600s 6. Sudar R A, Mathias L J . Novel thermooxidatively stable poly(ether-imide-benzoxazole) andpoly(ester-imide-benzoxazole). J PolymSci Part A: Polym Chem, 1994, 32; 2825–2839. doi:10.1002/pola.1994.080321504 7. Park K H, Kakimoto M, Imai Y . Synthesis and propertiesof new soluble aromatic polybenzoxazoles from 4,4-diamino-3,3-dihydroxytriphenylaminesand aromatic dicarboxylic acids. J PolymSci Part A: Polym Chem, 1998, 36: 1987–1993. doi:10.1002/(SICI)1099-0518(19980915)36:12<1987::AID-POLA3>3.0.CO;2-L 8. Hsiao S H, Dai L R . Synthesisand properties of novel aromatic poly(o-hydroxy amide)s and polybenzoxazoles based on the bis(ether benzoylchloride)s from hydroquinone and its methyl-, tert-butyl-, and phenyl-substitutedderivatives. J Polym Sci Part A: PolymChem, 1999, 37: 2129–2136. doi:10.1002/(SICI)1099-0518(19990701)37:13<2129::AID-POLA28>3.0.CO;2-O 9. Maglio G, Palumbo R, Tortora M . Aromatic poly(benzoxazole)sfrom multiring diacids containing (phenylenedioxy)diphenylene or (naphthalenedioxy)diphenylenegroups: synthesis and thermal properties. J Polym Sci Part A: Polym Chem, 2000, 38:1172–1178. doi:10.1002/(SICI)1099-0518(20000401)38:7<1172::AID-POLA16>3.0.CO;2-8 10. Maruyama Y, Oishi Y, Kakimoto M, Imai Y . Synthesisand properties of fluorine-containing aromatic polybenzoxazoles frombis(o-aminophenols) and aromaticdiacid chlorides by the silylation method. Macromolecules, 1988, 21: 2305–2309. doi:10.1021/ma00186a001 11. Hilborn J G, Labadie J W, Hedrick J L . Poly(aryl ether-benzoxazoles). Macromolecules, 1990, 23: 2854–2861. doi:10.1021/ma00213a006 12. Hsiao S H, Chen W T . Synthesesand properties of new aromatic polybenzoxazoles bearing ether andphenylethylidene or 1-phenyl-2,2,2-trifluoroethylidene linkages. J Polym Sci Part A: Polym Chem, 2003, 41: 914–921. doi:10.1002/pola.10630 13. Osaheni J A, Jenekhe S A . New red light-emitting conjugated rigid-rod polymer: poly(benzobisthiazole-1,4-phenylenebisvinylene). Macromolecules, 1993, 26, 4726–4728. doi:10.1021/ma00069a051 14. Osaheni J A, Jenekhe S A . Synthesis and processing of heterocyclic polymers as electronic,optoelectronic, and nonlinear optical materials. 1. New conjugatedrigid-rod benzobisthiazole polymers. ChemMater, 1992, 4: 1282–1290. doi:10.1021/cm00024a031 15. Osaheni A, Jenekhe S A . Enhancement of luminescence in polymer nanocomposites. Chem Mater, 1994, 6: 1906–1909. doi:10.1021/cm00047a002 16. Osaheni J A, Jenekhe S A . Electroactive and photoactive rod-coil copolymers: design, synthesis,and supramolecular regulation of photophysical properties. J Am Chem Soc, 1995, 117: 7389–7398. doi:10.1021/ja00133a012 17. Wang S, Guo P, Wu P, Han Z . Supramolecularregulation of photophysical properties and electron paramagnetic resonancestudies of novel rod-coil ordered copolymers based on poly(p-phenylene benzobisoxazole). Macromolecules, 2004, 37: 3815–3822. doi:10.1021/ma0498316 18. Wang S, Lei H, Guo P, Wu P, Han Z . Novel conjugated polymer poly(benzobisoxazole-2,6-diylvinylene):synthesis and evidence of aggregate formation in methanesulfonic acid. Eur Polym J, 2004, 40: 1163–1167. doi:10.1016/j.eurpolymj.2004.01.010 19. Zenon L, Midland M . USpatent, US4766244, 1988-08-23 20. Wang S, Bao G, Wu P, Han Z . Viscometricstudy on the interactions of polymers of the poly(benzazole) familywith nylon 66. Eur Polym J, 2000, 36: 1843–1852. doi:10.1016/S0014-3057(99)00267-0 21. Chen Y, Wang S, Zhuang Q, Li X, Wu P, Han Z . Spectral modulation and exciton migration in thiophene-basedpolybenzobisoxazole random copolymers with donor-acceptor architectures. Macromolecules, 2005, 38: 9873–9877. doi:10.1021/ma051516b 22. Liu Z, Wang S, Zhuang Q, Li X, Li F, Wu P, Han Z . Structure-variantexciton transfer and spatial confinement in statistical copolymersand blends based on polybenzazoles. ChemMater, 2007, 19: 1164–1169. doi:10.1021/cm0621500 23. So Y H . The effect of limited monomer solubility in heterogeneousstep-growth polymerization. Acc Chem Res, 2001, 34: 753–758. doi:10.1021/ar0100069 24. Wang S, Wu P, Han Z . Synthesis, characterization, and exciton confinementeffects in photopfhysical properties. JMater Sci, 2004, 39: 2717–2726. doi:10.1023/B:JMSC.0000021446.98019.d7 25. Fratini A V, Lenhert P G, Resch T J, Adams W W . Molecular packing and crystalline order in polybenzobisoxazoleand polybenzobisthiazole fibers. MaterRes Soc Symp Proc, 1989, 134: 431–445
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