Nanoblends of novel polyesters with polyaniline: Conductivity and heat-stability studies

Abstract

The present work initially deals with the fabrication of a new generation of polyesters (bearing thiophene, azomethine, thiourea and ether moieties) and subsequent blending with polyaniline (PAN) exhibiting extremely valuable nanoblend characteristics. Few poly(azomethine-thiourea-ester)s (PATEs), by the polycondensation of a new diol 4,4′-oxydiphenyl bis((E)-1-(4-hydroxobenzylidene)thiourea) with thiophene-2,5-dicarbonyl/terephtaloyl chloride, were synthesized. The polymers obtained were characterized by Fourier-transform infrared, proton-nuclear magnetic resonance, solubility, solution viscosity, gel permeation chromatography, thermogravimetric analysis, differential scanning calorimetry and wide-angle x-ray diffraction. The polymers exhibited high molar mass (77–89 × 10³) and thermal stability (T₁₀ 528–531°C, glass transition temperature (T_g) 265–268°C). Then the electrically conducting blends, of PAN dispersed in the PATEs matrix, were prepared by mash-blending and melt-blending techniques. Materials obtained by conventional melt-blending approach generated an efficient conductive network compared with those produced by mash blending. Field emission scanning electron microscopy images displayed nanoblend morphology of the melt-blended system, owing to increased physical interactions (hydrogen bonding and π–π stacking) between the two polymers. Moreover, miscible blends of thiophene-based PATE/PAN led to superior conductivity (1.5–2.1 S/cm) and heat stability (T₁₀ 503°C) even at low PAN concentration relative to previous thiophene, azomethine or PAN-based structures.

Keywords

poly(azomethine-thiourea-ester)s electrically conducting nanoblend morphology melt blending molar mass thermal stability

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References

Heeger

. Semiconducting and metallic polymers: the fourth generation of polymeric materials. Angew Chem Int Ed Engl 2001; 40(14): 2591–2611.

Kido

Lizumi

. Fabrication of highly efficient organic electroluminescent devices. Appl Phys Lett 1998; 73(19): 2721–2723.

MacDiarmid

. Synthetic metals: a novel role for organic polymers (Nobel lecture). Angew Chem Int Ed 2001; 40(14): 2581–2590.

Hoppe

Sariciftci

. Organic solar cells: an overview. J Mater Res 2004; 19(7): 1924–1944.

Stutzmann

Friend

Sirringhaus

. Self-aligned, vertical-channel, polymer field-effect transistors. Science 2003; 299(5614): 1881–1884.

Burroughes

Bradley

DDC

Brown

Marks

Mackay

Friend

. Light-emitting diodes based on conjugated polymers. Nature 1990; 347(6293): 539–541.

Davenas

Chouiki

Besbes

Ltajef

Ben Ouada

Bouazizi

. Influence of the molecular structure on the optical absorption and emission of PPV derivatives. Synth Met 2003; 139(3): 617–620.

Roncali

. Conjugated poly(thiophenes): synthesis, functionalization, and applications. Chem Rev 1992; 92(4): 711–738.

Gigli

Anni

Theander

Cingolani

Barbarella

. A novel electroluminescent oligothiophene. Synth Met 2001; 119(1–3): 581–582.

10.

Granstrom

. Novel polymer light-emitting diode designs using poly(thiophenes). Polym Adv Technol 1997; 8(7): 424–430.

11.

Ramos

MMD

Correia

HMG

Ribeiro

Stoneham

. Mesoscopic modelling of bipolar charge evolution in CN-PPV LEDs. Synth Met 2004; 147(1–3): 281–286.

12.

Chan

HSO

. A series of thienylene/phenylene-based polymers functionalized with electron-withdrawing or donating groups: synthesis and characterization. Macromolecules 2001; 34(13): 4314–4323.

13.

Adams

Bullock

Wilson

. Contribution to the structure of benzidine. J Am Chem Soc 1923; 45(2): 521–527.

14.

Tian

Xie

Gao

Hanif

. Highly efficient blue organic light-emitting devices based on improved guest/host combination. J Phys Chem C 2008; 112(31): 12024–12029.

15.

Skotheim

Elsenbaumer

Reynolds

(eds) Handbook of conducting polymers. 2nd ed. New York, NY: Marcel Dekker, Inc., 1998, p. 945.

16.

Grigoras

Catanescu

. Imine oligomers and polymers. J Macromol Sci C: Polym Rev 2004; C44(2): 1–37.

17.

D'Alelio

Crivello

Schoenig

Huemmer

. Polymeric Schiff bases. I. The synthesis and evaluation of polymeric Schiff bases prepared by Schiff-base exchange reactions. J Macromol Sci Chem 1967; A1(7): 1161–1249.

18.

Morgan

Kwolek

Pletcher

. Aromatic azomethine polymers and fibers. Macromolecules 1987; 20(4): 729–739.

19.

Yang

Jenekhe

SA.

Conjugated aromatic poly(azomethines). 1. Characterization of structure, electronic spectra, and processing of thin films from soluble complexes. Chem Mater 1991; 3(5): 878–887.

20.

Saegusa

Sekiba

Nakamura

Synthesis and characterization of novel 1,3,4-oxadiazole- or 1,3,4-thiadiazolecontaining wholly conjugated polyazomethines. J Polym Sci A: Polym Chem 1990; 28(13): 3647–3659.

21.

Yang

. Aromatic high-strength fiber. New York, NY: Wiley-Interscience, 1989, pp. 641–672.

22.

Barbera

Oriol

Serrano

. Hydroxy-functionalized liquid-crystalline polyazomethines. I. Synthesis, characterization and structure–structure–mesogenic behaviour relationship. Liq Cryst 1992; 12(1): 37–47.

23.

Narkis

Haba

Segal

Zilberman

Titelman

Siegmann

. Structured electrically conductive polyaniline/polymer blends. Polym Adv Technol 2000; 11(8–12): 665–673.

24.

Carothers

Natta

FJV.

Studies on polymerization and ring formation. III. Glycol esters of carbonic acid. J Am Chem Soc 1930; 52(1): 314–326.

25.

Shenoy

Pereira

Parikh

. Aromatic polyester based on bisphenol-A for liquid insulating systems: a synthetic approach. J Am Chem Soc 2004; 95(3): 606–614.

26.

Vert

Spenlehauer

Guerin

. Bioresorbability and biocompatibility of aliphatic polyesters. J Mater Sci: Mater Med 1992; 3(6): 432–446.

27.

Tamami

Yeganeh

. Preparation and properties of novel polyimides derived from 4-aryl-2,6-bis(4-amino phenyl)pyridine. J Polym Sci A: Polym Chem 2001; 39(21): 3826–3831.

28.

Liu

Wang

Yang

. Synthesis and characterization of new polybenzimidazopyrrolones derived from pyridine-bridged aromatic and dianhydrides. J Polym Sci A: Polym Chem 2004; 42(8): 1845–1856.

29.

Yang

Liu

Yang

Yin

Zhou

. Synthesis and properties of new polymerized monomer reactants matrix resins of pyrrolone–benzimidazole copolymers containing pyridine unit. J Appl Polym Sci 2004; 91(6): 3981–3990.

30.

Kausar

Zulfiqar

Ali

Ishaq

Sarwar

. Novel poly(thiourea-ether-imide)s derived from 4,4′-oxydiphenyl bis(thiourea): probing the possibility for high temperature applications. Polym Int 2011; 60(4): 564–570.

31.

Petreus

Vlad-Bubulac

Hamciuc

. New polyesterimides containing bulky, cyclic phosphorus groups. High Perform Polym 2008; 20(6): 588–600.

32.

Stejskel

Gilbert

RG.

Polyaniline. Preparation of a conducting polymer (IUPAC Technical Report). Pure Appl Chem 2002; 74(5): 857–867.

33.

Zilberman

Titelman

Siegmann

Haba

Narkis

Alperstein

. Conductive blends of thermally dodecylbenzene sulfonic acid-doped polyaniline with thermoplastic polymers. J Appl Polym Sci 1997; 66(2): 243–253.

34.

Ubale

Patil

Maldar

. Polyhydrazides based on 2,5-bis(4-carboxymethylene phenyl)-3,4-diphenyl thiophene. Eur Polym J 2007; 43(3): 1038–1045.

35.

Vlase

Doca

Ilia

. Thermo-oxidative degradation of polymers containing phosphorus in the main chain. High Perform Polym 2010; 22(7): 863–875.

36.

Thaker

Chothani

Dhimmar

Patel

Solanki

Patel

. Synthesis, characterisation and liquid crystalline properties of some Schiff base-ester central linkage involving 2,6-disubstituted naphthalene ring system. Liq Cryst 2012; 39(5): 551–569.

37.

Cristovan

Lemos

Pereira

. Systematic evaluation of the preparation of conducting PANI/ABS blends. J Appl Polym Sci 2010; 116(2): 825–831.