Abstract
Bis-aldehyde monomers 4-(4′-formyl-phenoxy)benzaldehyde (3a), 3-methoxy-4-(4′-formyl-phenoxy)benzaldehyde (3b), and 3-ethoxy-4-(4′-formyl-phenoxy)benzaldehyde (3c) were synthesized by etherification of 4-fluorobenzaldehyde (1) with 4-hydroxybenzaldehyde (2a), 3-methoxy-4-hydroxybenzaldehyde (2b), and 3-ethoxy-4-hydroxybenzaldehyde (2c), respectively. Each monomer was polymerized with p-phenylenediamine and 4,4′-diaminodiphenyl ether to yield six poly(azomethine)s. Single crystal X-ray diffraction structures of 3b and 3c were determined. The structural characterization of the monomers and poly(azomethine)s was performed by FT-IR and NMR spectroscopic techniques and elemental analysis. Physicochemical properties of polymers were investigated by powder X-ray diffraction, thermogravimetric analysis (TGA), viscometry, UV–vis, spectroscopy and photoluminescence. These polymers were subjected to electrical conductivity measurements by the four-probe method, and their conductivities were found to be in the range 4.0 × 10−5 to 6.4 × 10−5 Scm−1, which was significantly higher than the values reported so far.
Highlights
Conjugated organic semiconducting polymers have emerged as new materials having potential applications in electronics, opto-electronics, and photonics [1,2,3]
Physicochemical properties of polymers were investigated by powder X-ray diffraction, thermogravimetric analysis (TGA), viscometry, UV–vis, spectroscopy and photoluminescence
All2019, polyazomethines derived from aromatic dialdehydes were synthesized under N2 atmosphere by solution polycondensation
Summary
Conjugated organic semiconducting polymers have emerged as new materials having potential applications in electronics, opto-electronics, and photonics [1,2,3]. The imine bond (–CH=N–) is isoelectronic with the vinylene bond (–CH=CH–) [4,5,11,19], and the replacement of R and R0 with aromatic groups results in the formation of a conjugated structure When this conjugation extends throughout the polymer, this forms the basis of electronic conduction. Apart from that, their synthetic procedures, which are carried out under mild conditions, require condensation polymerization of dialdehydes with diamines, in a very simple way. Polymers 2019, 11, 1498 carried out for polymerization of carbon–carbon-linked conjugated structures [25] Products obtained from those coupling reactions, in addition, require a cumbersome purification process and isolation of catalysts [26,27].
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