Multiple-SO 3 H functioned ionic liquid as efficient curing agent for phthalonitrile-terminated poly(phthalazinone ether nitrile)
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4,5-Diphenylethynylphthalonitrile, 4,5-di(p-tert-butylphenylethynyl)phthalonitrile, 4,5-di(p-neopentoxyphenylethynyl)phthalonitrile, and 4,5-di(p-neopentoxyphenyl-1,3-butadiynyl)phthalonitrile were prepared via 4,5-diiodophthalonitrile and the appropriate alkyne in palladium-catalyzed coupling reactions. Condensation of the above alkynylphthalonitriles with lithium 1-octanolate in 1-octanol afforded the desired polyalkynylphthalocyanines, but only 2,3,9,10,16,17,22,23-octa (p-neopentoxyphenylethynyl)phthalocyanine and 2,3,9,10,16,17, 22,23-octa (p-neopentoxyphenylbutadnyl)phthalocyanine were soluble enough to be suitably characterized.Key words: phthalocyanines, phenylacetylenes, 1-phenyl-1,3-butadiynes.
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Abstract High curing temperature (including post‐curing temperature) and long curing time of phthalonitrile resins make them thermally stable but difficult to process. In this paper, novel mixed curing agents ( CuCl /4,4′‐diaminodiphenylsulfone ( DDS ) and ZnCl 2 / DDS ) were firstly designed for solving these problems. Bisphenol‐based phthalonitrile monomer ( BP ‐Ph; melting point: 228–235 °C) was synthesized and used as the curing precursor. Differential scanning calorimetry results indicated that BP ‐Ph cured with CuCl / DDS and ZnCl 2 / DDS exhibited curing temperatures close to the melting point of BP ‐Ph with curing ending temperatures of 225.4 and 287.1 °C, respectively. Rheologic investigations demonstrated obvious curing reactions of BP ‐Ph occurred with the mixed curing agents at 220 °C. Thermogravimetric analysis showed that BP ‐Ph cured by CuCl / DDS or ZnCl 2 / DDS maintained 95% mass at 573 or 546 °C, respectively, at a post‐curing temperature of 350 °C for 2 h. Reasonable long‐term thermo‐oxidative stability was also demonstrated. When the post‐curing temperature decreased to 290 °C, char yield at 800 °C of BP ‐Ph cured by CuCl / DDS was 77.0%, suggesting the curing procedure can be milder when using mixed curing agents. © 2017 Society of Chemical Industry
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4,5-Diphenylethynylphthalonitrile, 4,5-di(p-tert-butylphenylethynyl)phthalonitrile, 4,5-di(p-neopentoxyphenylethynyl)phthalonitrile, and 4,5-di(p-neopentoxyphenyl-1,3-butadiynyl)phthalonitrile were prepared via 4,5-diiodophthalonitrile and the appropriate alkyne in palladium-catalyzed coupling reactions. Condensation of the above alkynylphthalonitriles with lithium 1-octanolate in 1-octanol afforded the desired polyalkynylphthalocyanines, but only 2,3,9,10,16,17,22,23-octa (p-neopentoxyphenylethynyl)phthalocyanine and 2,3,9,10,16,17, 22,23-octa (p-neopentoxyphenylbutadnyl)phthalocyanine were soluble enough to be suitably characterized.Key words: phthalocyanines, phenylacetylenes, 1-phenyl-1,3-butadiynes.
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One of the major problems associated with phthalocyanines is their strong tendency to aggregate in both solution and the solid state. As a consequence, their application as sensors, optical filters and as photosensitisers in polar media can be limited. It is the target of this work to prepare a new series of phthalocyanines which possess an isolated core, by isolating the core aggregation between phthalocyanine rings will be eliminated.
The strategy employed involved the preparation of a 3 and 4 calix[4]arene substituted phthalonitrile. This was achieved in three steps and interestingly we were able to prepare a partial cone derivative for the 3-calix[4]arene phthalonitrile where the phthalonitrile is within the upper rim of the calix[4]arene. Such an arrangement places two of the t-butyl groups of the calix[4]arene above and below the phthalonitrile ring. Furthermore, this conformation was found to be stable at temperatures in excess of 120°C. On the other-hand the 4-calix[4]arene phthalonitrile gave both a partial cone and cone conformation.
We found that the 4-calix[4]arene phthalonitrile could be readily self-condensed to the tertacalix[4]arenephthalocyanine in good yields, on the other hand the 3- calix[4]arene phthalonitrile only yielded traces o f the phthalocyanine on selfcondensation, and this is due to steric congestion. The 3-calix[4]arene phthalonitrile was then cross-condensed with phthalonitrile to give the unsymmetrical monocalix[4]arenephthalocyanine, with the phthalocyanine perched into the upper rim of the calix[4]arene.
All calix[4]arene phthalocyanines were studied for aggregational behaviour in both polar solution and the solid state. It was found that the tetracalix[4]arene phthalocyanine does not show any aggregation either in the solid state or solution. The unsymmetricaPperched’ phthalocyanine does not aggregate in polar solution but forms dimers in the solid state.
Also reported within the thesis are the synthesis o f a series o f new novel calix[4]arene bridged binuclear phthalocyanines. Their synthesis and properties are discussed.
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The title compound, C21H14O2N2, consists of two substituted benzene rings and one phthalonitrile moiety. The dihedral angle between the first two benzene rings is 62.91 (1)°, and that between the phthalonitrile and the central benzene ring is 70.82 (1)°.
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The synthesis of a new phthalonitrile derivative (4-(benzo[d]thiazol-2-ylthio)phthalonitrile), its metal-free phthalocyanine, and metallo-phthalocyanines are described. Phthalocyanines are formed in high yield with template synthesis. These compounds showed considerable solubility in CHCl3, DMF and DMSO, a primary condition for potential applications. The newly synthesized compounds have been characterized by elemental analyses, UV-Visible spectra, IR and 1H-NMR.
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Binary blends composed of 1,3-bis (3,4-dicyanophenoxy) benzene (3BOCN) and ionic liquids (ILs) with different molecular structures were prepared.The curing behavior of these 3BOCN/ILs blends were studied by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and rheological analysis.The study suggested that the blends possessed a wide processing window and the structures of ILs (anion, cation and alkyl chain length at cation) had an effect on curing behavior.The 3BOCN/[EPy]BF 4 resins were prepared at elevated temperature.IR spectra of the resins showed that there were triazine and isoindoline formed in curing process.The TGA and dynamic mechanical analysis (DMA) revealed that the resins have excellent thermal stability together with high storage modulus and high glass transition temperature (T g ).Dielectric properties, long term oxidative aging and water uptake measurements of the resins suggested the IL brought some unique properties to the resins.
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