Synthesis, characterization and protonation study of novel poly(thioether imide)s based on aromatic heterocyclic diimide

Abstract

Novel poly(thioether imide)s were synthesized by 2,5-dimercapto-1,3,4-thiadiazole, and aromatic heterocyclic chlorodiimids through nucleophilic substitution reaction as alkali catalysts were presented. The poly(thioether imide)s exhibited good thermal property. The glass transition temperatures of polymers were around 373 °C, and 10% weight loss temperatures were in the range of 450–500 °C in nitrogen/air atmosphere. Meanwhile, the chloroform dilute solutions of these polymers could show strong UV-vis absorption peaks at about 289 nm. After being protonated by inorganic acids (HCl), the new shoulder absorption peaks were observed at 350 nm. The PL absorption bands of polymer solutions were in the region of 350–550 nm, which showed the green-yellow fluorescence.

Keywords

aromatic heterocyclic chlorodiimide / thermal stability / fluorescence / protonation

References

[1] Kim JY, Lee CW, Jang JG, . Orange Phosphorescent Organic Light-emitting Diodes using New Spiro [Benzoanthracene-fluorene]-type Host Materials[J]. Dyes Pigme., 2012, 94(2): 304-313.

[2] Barique MA, Seesukphronrarak S, Wu LB, . A Comparison Between Highly Crystalline and Low Crystalline Poly(Phenylene Sulfide) as Polymer Electrolyte Membranes for Fuel Cells[J]. J. Phys. Chem. B., 2011, 115(1): 27-33.

[3] Lombardo C, Ooi ZE, Danielson E, . Electrical Characteristics of Lateral Organic Bulk Heterojunction Device Structures[J]. Org. Electron., 2012, 13(7): 1 185-1 191.

[4] Wang CY, Zhao XY, Li G, . Novel Fluorinated Polyimides Derived from 9,9-bis(4-amino-3,5-difluorophenyl)Fluorene and Aromatic Dianhydrides[J]. Polym. Degrad. Stab., 2009, 94(10): 1 746-1 753.

[5] You NH, Higashihara T, Ando S, . Highly Refractive Polymer Resin Derived from Sulfur-Containing Aromatic Acrylate[J]. J. Polym. Sci., Part A: Polym. Chem., 2010, 48(12): 656-662.

[6] Yu YY, Chien WC, Wu TH, . Highly Transparent Polyimide/Nanocrystalline-titania Hybrid Optical Materials for Antireflective Applications[J]. Thin Solid Films, 2011, 520(5): 1 495-1 502.

[7] Saito J, Miyatake K, Watanabe M Synthesis and Properties of Polyimide Ionomers Containing 1H-1,2,4-Triazole Groups[J]. Macromolecules, 2008, 41(7): 2 415-2 420.

[8] Terraza CA, Liu JG, Nakamura Y, . Synthesis and Properties of Highly Refractive Polyimides Derived from Fluorene-bridged Sulfurcontaining Dianhydrides and Diamines[J]. J. Polym. Sci., Part A: Polym. Chem., 2008, 46(4): 1 510-1 520.

[9] Wei HB, Fang XZ, Han Y, . Synthesis and Characterization of Poly(Thioether Ether Sulfone Imide)s Derived from Isomeric Bis(Chlorophthalimide)s and Bis(4-Mercaptophenyl) Sulfone[J]. Eur. Polym. J., 2010, 46(2): 246-253.

[10] Nakagawa Y, Suzuki Y, Higashihara T, . Synthesis of Highly Refractive Poly(phenylene thioether) Derived from 2,4-Dichloro-6-alkylthio-1,3,5-triazines and Aromatic Dithiols[J]. Macromolecules, 2011, 44(23): 9 180-9 186.

[11] Ma L, He L, Gan MY, . Influence of Different Substrates on the Electrochromic Property of Polyaniline Films[J]. J. Wuhan Univ. Technology-Mater. Sci. Ed., 2010, 25(4): 545-549.

[12] Zhao XY, Wang CY, Chen L, . Novel Poly(fluorinated Imide)s Containing Naphthalene Pendant Group: Synthesis and Characterization[J]. Colloid Polym. Sci., 2009, 287(11): 1 331-1 337.

[13] Patil PS, Haram NS, Pal RR, . Synthesis, Spectroscopy, and Electrochemical Investigation of New Conjugated Polymers Containing Thiophene and 1,3,4-thiadiazole in the Main Chain[J]. J. Appl. Polym. Sci., 2012, 125(3): 1 882-1 889.

[14] Ke HZ, Luo W, Cheng GE, . Formation of CuS Pineal Microspheres Via a Pyridine-solvothermal Process[J]. J. Wuhan Univ. Technology-Mater. Sci. Ed., 2010, 25(3): 459-463.

[15] Zhou G, Cheng YX, Wang LX, . Novel Polyphenylenes Containing Phenol-Substituted Oxadiazole Moieties as Fluorescent Chemosensors for Fluoride Ion[J]. Macromolecules, 2005, 38(6): 2 148-2 153.

[16] Wang YQ, Park JS, Leech JP, . Poly(Aryleneethynylene)s with Orange, Yellow, Green, and Blue Solid-State Fluorescence[J]. Macromolecules, 2007, 40(6): 1 843-1 850.

[17] Gui YP, Khouri J, Fouad F, . Method For The Preparation Of Bis(Haloimides)[P], 2005

[18] Liaw DJ, Wang KL, Chang FC, . Novel Poly(pyridine imide) with Pendent Naphthalene Groups: Synthesis and Thermal, Optical, Electrochemical, Electrochromic, and Protonation Characterization[J]. J. Polym. Sci. Part A Polym Chem., 2007, 45(12): 23672-2374.

[19] Mamtimin X, Tuerxun T, Aikebaierjiang A, . Synthesis, Characterization, and Protonation of Poly(2-N,N-dimethylamino-4,6-bis(2-furan)-pyrimidine)[J]. Fiber Polym., 2010, 11(2): 158-163.