Synthesis and characterization of novel conductive copolymer poly[(phenylazepane-2-one)-co-(pyrrole)] with improved solu
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Synthesis and characterization of novel conductive copolymer poly[(phenylazepane-2-one)-co-(pyrrole)] with improved solubility and conductivity properties Djamal Eddine Kherroub1,*, Larbi Bouhadjar2, and Ahmed Boucherdoud3 1
Laboratoire de Chimie des Polymères, Université Ahmed Ben Bella d’Oran 1, BP 1524, 31000 Oran, Algeria Faculté des Sciences de la Matière, Université Ibn Khaldoun de Tiaret, BP P78, Zaâroura, 14000 Tiaret, Algeria 3 Laboratoire de Structure, Elaboration et Application des Matériaux Moléculaires (SEA2M), Université Abdelhamid Ibn Badis de Mostaganem, 27000 Mostaganem, Algeria 2
Received: 16 May 2020
ABSTRACT
Accepted: 7 September 2020
An effective technique is proposed in this study to synthesize a novel polymer, based on the copolymerization of pyrrole with a synthesized monomer (phenylazepane-2-one), combining the character of both conductivity and solubility. The reaction was cationically catalyzed, using an acid exchanged clay (Maghnite-H?) as an ecological catalyst. The reaction synthesis of poly[(phenylazepane-2-one)-co-(pyrrole)] abbreviated poly(PAP) has been carried out in dichloromethane. The reaction yield was 85% at a temperature of 25 °C for 4 h using 4% of catalyst. Chemical structures have been characterized by proton and carbon nuclear magnetic resonance (1H-NMR and 13C-NMR), ultraviolet/visible spectroscopy (UV–Vis) and Fourier transform infrared spectroscopy (FT-IR). Thermal properties have been evaluated by differential scanning calorimetry and thermal gravimetric analysis, showing the thermal stability of the poly(PAP) up to 333 °C. Solubility tests confirmed the solubility of poly(PAP) in various common solvents. The indirect band-gap was found 1.22 eV using Tauc’s formula. The semiconductor behavior poly(PAP) has been proven by the evolution of ac electrical conductivity and dielectric properties as a function of frequency and temperature. These new properties allow direct application of poly(PAP) on all desired surfaces rather than conventional materials.
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Springer Science+Business
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Handling Editor: Gregory Rutledge.
Address correspondence to E-mail: [email protected]
https://doi.org/10.1007/s10853-020-05334-7
J Mater Sci
GRAPHIC ABSTRACT O
H N
Acetic anhydride
Caprolactam
OH
T = 70 °C
° d001 = 12.50 A
t=2h
+ H2SO4
Phenol
86%
raw-Maghnite 48 h ° d001 = 15.02 A
+ 2
H 3O
O
3HC
N
Maghnite-H+
1-Phenylazepan-2-one (PA) H N T = 25 °C t=4h
Pyrrole 85% H N
O
N
n Poly(Phenylazepane-2-one-pyrrole) Poly(PAP)
COOH
J Mater Sci
Introduction Conductive polymers are an exciting new class of electronic materials [1–4], which had a rapid brought and increasing interest since Shirakawa’s report in 1977 [5]. Since they have combined properties of metals and polymers, the conductive polymers have found applications in the fields of battery materials, electrochromic devices, electromagnetic shielding, sensor technology, nonlinear optics, molecular electronics and enzyme immobilization matrices [6–8].
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