Synthesis and Characterization of Fully Aromatic Polyazomethines with Cyano Functional Group
Vol. 55, No. 2, pp. 124-129,
Apr. 2018
10.12772/TSE.2018.55.124
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Abstract
We herein report the preparation and characterization of a new type of fully
aromatic polyazomethines (PAMs) with the cyano functional group. For synthesizing
this compound, two homopolymers, poly(nitrilo-2-cyano-1,4-phenylenenitrilomethine-
1,3-phenylenemethine) (mPAM) and poly(nitrilo-2-cyano-1,4-phenylenenitrilomethine-
1,4-phenylenemethine) (pPAM) and their copolymers, poly[(nitrilo-2-cyano-1,4-
phenylenenitrilomethine-1,4-phenylenemethine)-co-(nitrilo-2-cyano-1,4-phenylenenitrilomethine-
1,3-phenylenemethine)]s (coPAMs), were synthesized via the polycondensation of
terephthalaldehyde (TPA), isophthalaldehyde (IPA), and 2-cyano-1,4-phenylenediamine
(cyPPD) monomers in an NMP/CaCl2 solvent system. The 1H-NMR and FT-IR spectra confirmed
that all the aromatic PAMs were successfully synthesized and that the output compositions
of coPAMs were almost identical to the relative input composition of TPA and IPA
to cyPPD. mPAM, with a nonlinear meta-phenylene moiety, exhibited good solubility in
organic solvents such as NMP, DMSO, and DMAc, while pPAM and coPAMs were partially
soluble in those solvents owing to the rigid para-phenylene moiety in the main chains.
Accordingly, unlike mPAM, pPAM and coPAMs were semicrystalline, as revealed by their Xray
diffraction patterns. Interestingly, the peak decomposition temperatures (667−769 °C)
in air were higher than those (452−594 °C) in nitrogen, although the residues (74−81%) at
800 °C in nitrogen were far higher than those (16−47%) in air.
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