Synthesis and Optoelectronic Properties of Novel Polyamides with 2‐Naphthyldiphenylamine Units

Abstract

A new series of electroactive polyamides is synthesized from N,N′‐bis(4‐aminophenyl)‐N,N′‐di‐2‐naphthyl‐1,4‐phenylenediamine (2) with four dicarboxylic acids via the phosphorylation polyamidation technique. These polyamides are amorphous with good solubility in many organic solvents and can be solution‐cast into flexible and strong films. They exhibit moderately high thermal stability with glass‐transition temperatures in the range of 247–289 °C. The polyamide 4a derived from a cycloaliphatic dicarboxylic acid reveals stronger fluorescence emission than those derived from aromatic ones, and it also shows a marked solvent effect on the fluorescence profile. All the electroactive polymer films show reversible electrochemical oxidation accompanied by strong color changes from the colorless neutral state to yellowish–green and blue oxidized states.

Highly efficient microwave-assisted synthesis of photoactive polyamides bearing 5-(3-acetoxynaphthoylamino)benzamide moieties

“…151 C Decomposition (Dec.). FTIR (KBr, cm (6). Into a 25-mL round-bottomed flask fitted with a magnetic stirrer was placed a solution of 0.49 g (2.72 Â 10 À3 mol) of 5-aminoisophthalic acid in 2 mL of DMAc.…”

“…Finally, it was refluxed for 30 min, and then the mixture was poured into 100 mL/5 mL of cold water/concentrated hydrochloric acid. The precipitate was collected by filtration, washed thoroughly with water, and dried at 70 C for 6 h to yield 1.31 g (94%) of diacid (6). m.p.…”

“…The synthetic route for the preparation of the new dicarboxylic acid, 5-[4-(3-acetoxynaphthoylamino)benzoylamino]isophthalic acid (6), is depicted in Figure 1. In the first step, the reaction of 3-hydroxynaphthalene-2-carboxylic acid with acetic anhydride in the presence of sulfuric acid afforded the compound (2).…”

“…The incorporation of naphthalene, as a pendent group in a polymer chain, has caused decreased crystallinity and enhanced solubility and thermal stability. [4][5][6] Microwave-induced reactions have received extensive interest, because reactions under microwave irradiation are in general not only faster compared with the conventional heating reactions but also potentially more efficient, cleaner, and safer. 7 Further improvements have also been reported, which can offer increased reaction rates, higher yields, and greater selectivity to the targeted product under milder reaction conditions.…”

Synthesis, Characterization of New Polyamides Bearing Triarylamine for Lightemitting Diodes

“…The introduction of withdrawing groups improves the oxidation resistance, optical transparency and solubility in organic solvents and lead to decrease the crystallinity behavior, dielectric constant, water absorption and color [19][20][21][22]. Polyamides are called conducting polymer, are important part of electrochromic materials and have being developed [23][24][25][26]. Electrochromic materials can convert color reversibly by mean of important result of energy saving and sufficient electrochemical potential or redox steps.…”