Synthesis and Characterization of Novel Aromatic Polyamides Bearing CF 3 , Quinoxaline-Anthraquinone Pendants: Study of Photophysical and Electrochemical Properties by Using Nanocomposite Electrode Paste Mousa Ghaemy, Arameh Masoumi, Seyed Mojtaba Amini Nasab, Marjan Hassanzadeh Polymer Chemistry Research Laboratory, Department of Chemistry, University of Mazandaran, Babolsar, 47416-95447, Iran Correspondence to: M. Ghaemy (E-mail: ghaemy@umz.ac.ir) ABSTRACT: A new aromatic diamine, 2,3-bis(4-(4-amino-2-(trifluoromethyl) phenoxy)phenyl)naphtho[2,3-f]quinoxaline-7,12-dione, was synthesized and fully characterized by using FTIR, 1 H and 13 C NMR, DEPT technique, and elemental analysis. A series of novel fluorescent anthraquinone-quinoxaline containing polyamides (PAs) with inherent viscosities of 0.39–0.62 dL/g was prepared by direct polycondensation of the diamine with various dicarboxylic acids. These PAs were readily soluble in many polar aprotic organic sol- vents and could be solution-cast into tough and flexible films. The PAs exhibited glass transition temperatures (T g )s between 230 and 323  C, and 10% weight loss temperatures in the range of 362–433  C in N 2 . All of the PAs have fluorescence emission in solution and in solid state with maxima around 452–510 nm and with the quantum yields in the range of 6–17%. Also, cyclic voltammetry (CV) method was used to study the electrochemical oxidation behavior of these polymers at the surface of a modified multiwalled carbon nanotube (MWCNT)s glassy electrode. V C 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 127: 3169–3177, 2013 KEYWORDS: polyamides; quinoxaline; anthraquinone; solubility; photophysical; thermal properties Received 12 November 2011; accepted 16 March 2012; published online 19 May 2012 DOI: 10.1002/app.37714 INTRODUCTION One of the problems in high-temperature polymers such as aro- matic PAs with excellent thermal and mechanical properties is their poor processability because of their high melting or soft- ening temperatures and insoluble nature in most organic sol- vents. 1–3 Therefore, much effort has been made to modify the structure of PAs in order to have better properties in terms of both solubility and processability with protection of their high thermal stability. The successful approaches employed for those purposes include: introduction of flexible bonds (e.g., AOA, ASO 2 A, etc.), 4–8 replacing symmetrical aromatic rings with unsymmetrical ones 9,10 and alicyclic units 11–13 into the polymer backbone or as bulky side groups 14–23 and forming a noncopla- nar structure, thereby, do not allowing crystallization. It has also been recognized that the incorporation of aryl-ether link- ages in aramids backbone generally impart an enhanced solubil- ity and processability without substantial diminution of thermal properties. In recent years, considerable attention has been cur- rently devoted to the fluorinated aromatic polyamides. It was found that the incorporation of flexible fluorinated groups into polyamide backbones resulted in great benefits for improving polymer solubility and thermal stability as well as electrical and dielectric performance. 24–27 As part of the efforts to gain the high-performance polymers with good solubility for advanced microelectronics applications, this article mainly reports the synthesis and characterization of a series of novel PAs bearing several functional groups in their backbone such as flexible ether linkage, and CF 3 and quinoxa- line-anthraquinone pendants. These PAs were fully characterized and their properties such as solubility, thermal, photophysical, and electrochemical behavior were investigated. EXPERIMENTAL Materials and Measurements All chemicals were purchased either from Merck or Fluka NMP was purified by distillation under reduced pressure over calcium hydride and stored over molecular sieves 4 A ˚ .K 2 CO 3 was dried for 24 h at 120  C under vacuum. All other reagents and sol- vents were used as received from commercial sources. 1 H NMR and 13 C NMR spectra were recorded on a 400 MHz and 100 MHz Bruker Advance DRX instrument respectively using DMSO-d 6 as solvent and tetramethyl silane as an internal Additional Supporting Information may be found in the online version of this article. V C 2012 Wiley Periodicals, Inc. WWW.MATERIALSVIEWS.COM WILEYONLINELIBRARY.COM/APP J. APPL. POLYM. SCI. 2013, DOI: 10.1002/APP.37714 3169