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Vol. 26 No. 1 (2014): Vol 26 Issue 1

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Synthesis, Characterization, Effect of Triaryl Ring Substituents Groups on Thermal and Spectral Properties of New Soluble Triphenylamine-Based Aromatic Polyamides

https://doi.org/10.14233/ajchem.2014.15331
Azhar Kamil Rashid
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia, University of Baghdad, Baghdad, Iraq
Rosiya Binti Yahya
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
Phang Sook Wai
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia

Corresponding Author(s) : Azhar Kamil Rashid

azhar_almasody@yahoo.co.uk

Asian Journal of Chemistry, Vol. 26 No. 1 (2014): Vol 26 Issue 1

Abstract

Three new triphenylamine-containing aromatic diacid monomers, 4,4'-dicarboxy-4'’-isopropyl-triphenylamine (Ma), 4,4'-dicarboxy-2’4'’-dimethyl-triphenylamine (Mb, 4,4'-dicarboxy-4'’-ethyltriphenylamine (Mc) were successfully synthesized via the aromatic nucleophilic fluoro-displacement reaction of 4-fluorobenzonitrile with aniline-derivatives using sodium hydride as the base, followed by alkaline hydrolysis of the dinitrile intermediates (Ia), (Ib), (Ic). A series of poly(amine-amide)s were prepared by the direct phosphorylation polycondensation from the newly synthesized diacid monomers with various aromatic diamines. FTIR, 1H and 13C NMR spectroscopic techniques were used to identify the chemical structures of the dicyano intermediates, the carboxylic acid monomer and the resultant poly(amine-amide)s. These aromatic poly(amine-amide)s were found to be readily soluble in a variety of organic solvents and could afford strong and tough films via solution casting. They exhibited excellent thermal stability associated with high glass transition temperatures (Tg = 248.32-290.46 ºC) and 10 % weight loss temperatures in excess of 522 ºC in nitrogen. In dilute N-methyl pyrrolidone solution, these polymers exhibited a medium to strong photoluminescence in the blue region at (425-443) nm. Cyclic voltammetry of the poly(amine-amide)s films cast onto an ITO-coated glass substrate in dry acetonitrile containing 0.1 M of tetrabutylammonium perchlorate (TBAP) as an electrolyte exhibited one oxidation redox couples (Eonset) at (1.30-1.37) V versus Ag/AgCl and revealed electrochromic characteristics with a colour change from pale yellow to blue at applied potentials switched between 0.0 and 1.6 V.

Keywords

Hole-transporting materials Triphenylamine Emitting Layer
Kamil Rashid, A., Binti Yahya, R., & Sook Wai, P. (2013). Synthesis, Characterization, Effect of Triaryl Ring Substituents Groups on Thermal and Spectral Properties of New Soluble Triphenylamine-Based Aromatic Polyamides. Asian Journal of Chemistry, 26(1), 85–92. https://doi.org/10.14233/ajchem.2014.15331
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