Synthesis and properties of polybenzazoles containing flexible methylene in backbone

XU Xiaohui, LIU Xiaoyun, ZHOU Chengjun, ZHUANG Qixin, HAN Zhewen

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PDF(133 KB)
Front. Chem. Sci. Eng. ›› 2008, Vol. 2 ›› Issue (4) : 412-416. DOI: 10.1007/s11705-008-0073-5

Synthesis and properties of polybenzazoles containing flexible methylene in backbone

  • XU Xiaohui, LIU Xiaoyun, ZHOU Chengjun, ZHUANG Qixin, HAN Zhewen
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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.

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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

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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