Facile synthesis of heat‐resistant and photoluminescent poly(N‐aryleneindole ether)s via catalyst‐free CN/CO coupling reaction

Abstract

We present here a novel programmable polymerization route for the synthesis of new indole‐based polymers via a catalyst‐free nucleophilic substitution reaction. The polycondensation of 4‐hydroxyindole with different activated difluoro monomers undergoes in N‐methylpyrrolidinone, affording soluble poly(N‐aryleneindole ether)s (PEINs) with high molecular weights (Mw up to 486,000) in high yields (up to 96%). The structures of the polymers are characterized by means of FT‐IR, 1H NMR spectroscopy and elemental analysis, the results show good agreement with the proposed structures. The resulting polymers are processable and enjoy high glass transition temperatures (Tgs > 180 °C) and thermal stability (Tds > 420 °C). Thin films of PEINs show great mechanical behaviors with high tensile strength up to 104 Mpa, and good optical transparency. In addition, due to the indole moieties in the main chains, all these PEINs are endowed with significantly strong photonic luminescence in chloroform and display highly solvent‐dependent emission bands. Especially, the polymer PEIN‐3 carrying sulfonyl units, shows outstanding blue‐light emission with high quantum yields (45.2%, determined against quinine sulfate). The results obtained by cyclic voltammetry suggest that PEINs possess good electroactivity. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 313–320

Synthesis of high-performance polymers via copper-catalyzed amination of dibromoarenes with primary aromatic ether diamines

“…Synthesis of phenyl-(4-phenylamino-phenyl)-methanone. The synthesized polymers were characterized by FTIR, 1 H NMR and elemental analyses, the results of which were consistent with the proposed structures. As an example, the 1 H NMR spectrum of PIEKs was given in Figure 1 (DMSO-d 6 ).…”

“…The combined organic layers were washed with brine, dried over anhydrous Na 2 SO 4 , concentrated, and the resulting residue was purified by column chromatography on silica gel to provide the yellow product. Yield: 92%; 1 Synthesis of Poly(imino ether ketone)s. A typical synthesis of PIEKs was conducted in a two-necked flask (50 mL) equipped with a magnetic stirrer, a nitrogen outlet, inlet, and water-cooled condenser. Aryl halides (4.0 mmol), primary aromatic diamines (4.0 mmol) copper-catalyst (0.8 mmol), DMSO (10 mL) and KOH (8.0 mmol) were added to this flask (Scheme III).…”

“…FTIR spectra was recorded on a Nicolt 6700 FTIR spectrometer. 1 H NMR was performed on AVANCE 300 MHz NMR spectrometers in dimethylsulfoxide (DMSO)-d 6 . The elemental analysis characterization technique was measured on a Vario EL III apparatus.…”

“…Heat resistant polymer rises in response to the proper time and conditions and becomes the focus of attention. [1][2][3] Especially, as one of the most promising class of heat-resistant engineering polymers, poly(ether ether ketone) (PEEK) is widely applied due to the outstanding properties, such as thermal stability and chemical stability. 4,5 However, the availability of such polymers is limited to a certain extent for a variety of reasons, such as the relatively low glass transition temperature (T g ) and poor solubility.…”

Soluble N‐substituted poly(benzimidazole imide)s via C−N coupling reaction

“…We expected the prepared PBIIs to show outstanding solubility and to enjoy the ability to dissolve in polar organic solvents. The polymer solubility was qualitatively determined by the dissolution of 5 mg of solid polymers in 1 mL of organic solvent at room temperature and 50 o C (Table ) . PBIIs were found to be easily soluble in high polar solvents, such as N ‐methyl‐2‐pyrrolidone and dimethylacetamide, whereas they were partially soluble in common organic solvents such as DMSO, dimethylformamide and chloroform.…”