Abstract
Aromatic bis-aldehydes have been used as building blocks in the synthesis of polyazomethines (a class of conjugated Schiff bases) and their physicochemical properties have been studied. Six dialdehydes have been synthesized, 3a-3f, via etherification reaction between aromatic diols (2a-2f) and 4-fluorobenzaldehyde (1) (see Scheme 1), and then polymerized with 1,4-phenylenediamine (4a) and 4,4′-oxydianiline (4b) (see Scheme 2). The chemical structures of the bis-aldehydes were elucidated by FTIR, 1H NMR and 13C NMR spectroscopic studies, elemental analysis and single crystal whereas the polymers were studied by FTIR and NMR spectroscopy. Their physicochemical properties were examined by their inherent viscosity, organosolubility, differential scanning calorimetry, X-ray powder diffraction, thermogravimetric analysis, solvatochromism, and photoluminescence. We report the electrical conductivity of each polymer measured by the four probe method. The results indicate that the electrical conductivity of polymers lies in range 0.019–0.051 mScm−1 which is reasonably higher than any reported value.
Highlights
Conducting polymer based semiconductors have become a dominant platform for modern electronics.[1]
As one class of conducting polymers, polyazomethines (PAM) have attracted considerable attention, for example, the azomethine linkage is a renowned mesogen in liquid crystalline polymers.[7,8]
All chemicals used in the synthesis of bis-aldehydes and PAM were purchased from commercial suppliers and were of high purity
Summary
Conducting polymer based semiconductors have become a dominant platform for modern electronics.[1]. As one class of conducting polymers, polyazomethines (PAM) (with the azomethine linkage in the polymer backbone) have attracted considerable attention, for example, the azomethine linkage is a renowned mesogen in liquid crystalline polymers.[7,8] The –C(H)=N– bond of PAM is isoelectronic with the –CH=CH– group and has a similar planar molecular structure with the –CH=CH– group.[9] As PAM type systems are capable of being protonated and complexed with metals, by taking the advantage of these characteristics, PAM materials have potential applications in electronics, optoelectronics, and photonics.[10,11] The increased interest in this class of polymers is due to their high thermal stability, metal chelating ability, excellent mechanical strength, semi-conducting, and excellent optoelectronic properties.[12] Owing to these brilliant properties they are used to prepare composites, graphite materials, epoxy oligomer, photoresists, and block copolymers.[13,14] In terms of synthesis, it is expedient to synthesize PAM by polycondensation of the appropriate amine and carboxaldehyde. In this article we report the syntheses and characterization
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