Topic
Phthalonitrile
About: Phthalonitrile is a research topic. Over the lifetime, 1595 publications have been published within this topic receiving 21677 citations. The topic is also known as: 1,2-dicyanobenzene & o-benzenedinitrile.
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TL;DR: In this paper, an improved approach to the synthesis of di-disubstituted phthalocyanines from two different phthalyl precursors is described, which combines substituted 1,3 diiminoisoindoles and 6/7-nitro-1,3,3-trichloroisoindolenine to synthesize phTHC.
Abstract: An improved approach to the synthesis of di-disubstituted phthalocyanines from two different phthalyl precursors is described. The method combines substituted 1,3 diiminoisoindoles and 6/7-nitro-1,3,3-trichloroisoindolenine to synthesize phthalocyanine. The method can be applied to the synthesis of hydrogen and metallo phtahlocyanine. The yields are variable, ranging from 17% to 72% depending on the substituents.
513 citations
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TL;DR: In this article, boron trihalide-induced cyclotrimerization of adequately substituted derivatives of phthalonitrile in 1,2-dicyanobenzene derivatives has been made taking into account the high reactivity of the Lewis acid BCl3 toward many functional groups.
Abstract: Novel boron(III) subphthalocyanines (SubPcs) soluble in organic solvents containing a variety of donor and acceptor substituent groups have been synthesized by boron trihalide-induced cyclotrimerization of adequately substituted derivatives of phthalonitrile in 1-chloronaphthalene. The choice of the substituents on the 1,2-dicyanobenzene derivatives has been made taking into account the high reactivity of the Lewis acid BCl3 toward many functional groups. Considering this limitation, we set out to synthesize phthalodinitriles equipped with iodo, nitro, alkyl- or arylthio, alkyl- or arylsulfonyl groups that are sufficiently stable under the required reaction conditions and also provide an easily accessible set of acceptor/donor substituents. The quadratic and cubic hyperpolarizabilities of these compounds as well as their linear optical and electrochemical properties have been measured by several techniques, including EFISH (at two wavelengths), HRS, and THG, steady-state and time-resolved absorption and f...
264 citations
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TL;DR: In this article, a 1,3-bis(3,4-dicyanophenoxy)benzene was synthesized in high yield by a simple nucleophilic displacement of a nitro-substituent from 4-nitrophthalonitrile in a dipolar aprotic solvent.
240 citations
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TL;DR: An aromatic, diether-linked phthalonitrile resin, prepared from 4,4′-bis(3,4-dicyanophenoxy)biphenyl, exhibits excellent thermo-oxidative properties as discussed by the authors.
Abstract: An aromatic, diether-linked phthalonitrile resin, prepared from 4,4′-bis(3,4-dicyanophenoxy)biphenyl, exhibits excellent thermo-oxidative properties. The resin is easily processed from the melt of the monomer in a controlled manner as a function of the amine curing agent and processing temperatures. Polymerization occurs by a cyclic addition reaction without the formation of volatile by-products. The polymerization reaction can be stopped at a prepolymer stage. The prepolymer can be stored indefinitely at ambient conditions without further reaction. The modulus and viscoelastic properties of the resin were found to be a function of the postcuring conditions.
217 citations
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TL;DR: In this article, a multiple aromatic ether linked phthalonitrile was synthesized and characterized, which exhibited good structural integrity upon heating to elevated temperatures and exhibited excellent thermal properties along with long-term oxidative stability.
Abstract: A multiple aromatic ether linked phthalonitrile was synthesized and characterized. The oligomeric phthalonitrile monomer was prepared from the reaction of an excess amount of bisphenol A with 4,4'-difluorobenzophenone in the presence of K 2 CO 3 as the base in an N,N-dimethylformamide/toluene solvent mixture, followed by end capping with 4-nitrophthalonitrile in a two-step, one-pot reaction. The monomer properties were compared to those of the known resin 2,2-bis[4-(3,4-dicyanophenoxylphenyl]propane after being cured in the presence of bis[4-(4-aminophenoxy)-phenyllsulfone. Rheometric measurements and thermogravimetric analysis showed that the oligomeric phthalonitrile resin maintained good structural integrity upon heating to elevated temperatures and exhibited excellent thermal properties along with long-term oxidative stability. The ether-linked phthalonitrile resin absorbed less than 2.5% water by weight after exposure to an aqueous environment for extended periods.
209 citations