New polymer syntheses. IX. Synthesis and properties of new conducting polyazomethine polymers containing main chain cycloalkanone and pyridine moieties

Citation
Ki. Aly et Aa. Khalaf, New polymer syntheses. IX. Synthesis and properties of new conducting polyazomethine polymers containing main chain cycloalkanone and pyridine moieties, J APPL POLY, 77(6), 2000, pp. 1218-1229
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science","Material Science & Engineering
Journal title
JOURNAL OF APPLIED POLYMER SCIENCE
ISSN journal
00218995 → ACNP
Volume
77
Issue
6
Year of publication
2000
Pages
1218 - 1229
Database
ISI
SICI code
0021-8995(20000808)77:6<1218:NPSISA>2.0.ZU;2-8
Abstract
Novel polyazomethines containing cycloalkanones or pyridine moieties were s ynthesized by the polycondensation of 2,5-bis(m-aminobenzylidene)cyclopenta none (BMAP, IV), 2,6-bis(m-aminobenzylidene)cyclohexanone (BMAH, V), 2,6-bi s(p-aminobenzylidene)cyclohexanone (BPAH, VI), and 2,6-bis(m-aminostyryl)py ridine (BMAS, WI) diamines with terephthalaldehyde in EtOH at 25 degrees C. These polymers were yellow to orange in color, had reduced viscosities up to 1.42 dL/g, and had electric conductivities as high as 10(-11)-10(-12) S cm(-1). All th, polyazomethines were insoluble in common organic solvents b ut dissolved completely in concentrated sulfuric acid. However, they were r eadily hydrolyzed in concentrated H2SO4. X-ray diffraction diagrams showed that the crystallinities of the polyazomethines were low. These azomethine polymers showed high thermal and thermooxidative stability and exhibited no appreciable decomposition up to 400 degrees C in air. The electronic spect ra of the polymers indicated a large bathochromic shift of the pi-pi* absor ption band (similar to 360 nm) that was due to the presence of C=N bonds in the polymer main chain. Doping with iodine dramatically raised the conduct ivity and produced dark brown to black colored semiconductive polymers with a maximum conductivity on the order of 10(-7) S cm(-1) Furthermore, the mo rphology of selected examples of the four polyazomethines was examined by s canning electron microscopy. (C) 2000 John Wiley & Sons, Inc.