Polymerization of Bisphthalonitriles: Metal Free Phthalocyanine Formation

Marullo, N. P.; Snow, Arthur W.

doi:10.1021/bk-1982-0195.ch025

Cited by 17 publications

(13 citation statements)

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“…Synthesis of mononuclear phthalocyanines, soluble in organic solvents Treatment of 4-nitrophthalonitrile (1) with 2-propanol (2), 2-methy I-I -propano1 (3), and 2,2-dimethyl-I-propanol(4) with potassium carbonate in dimethylformamide (DMF) in a useful modification (15) of published procedures (16,17) gave in some instances at high temperatures the unwanted by-products 4-hydroxyphthalonitrile (5) (18) and bis(3,4-dicyanopheny1)-ether (6), but at room temperature (15) the desired 4-isopropoxyphthalonitrile (7) (1 1, 15), 4-isobutoxyphthalonitrile (8), and 4-neopentoxyphthalonitrile (9) respectively in 69 to 87% yield. Phthalonitriles 7-9 were readily converted, using gaseous ammonia and sodium methoxide in methanol (19,20), to 5-isopropoxy-l,3-diiminoisoindoline (lo), 5-isobutoxy-1,3-diiminoisoindoline (11), and 5-neopentoxy-l,3-diiniinoisoindoline (12) respectively.…”

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confidence: 99%

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Metallophthalocyanine dimers incorporating five-atom covalent bridges

Leznoff¹,

Marcuccio²,

Greenberg³

et al. 1985

Can. J. Chem.

159

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confidence: 99%

“…The symmetrical diol forming this bridge should not have hydrogen atoms available for p-elimination. Treatment of excess 2-hydroxymethyl-2-methyl-1,3-propanediol (16) with triphenylmethyl chloride (trityl chloride) in pyridine yielded upon column chromatography 68% (based on trityl chloride) of 2-methyl-2-trityloxymethyl-1,3-propanediol (17).…”

mentioning

confidence: 99%

Metallophthalocyanine dimers incorporating five-atom covalent bridges

Leznoff¹,

Marcuccio²,

Greenberg³

et al. 1985

Can. J. Chem.

159

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“…The conversion to the octaa-substituted phthalocyanine proved to be very troublesome and very low in yield. Attempts involving the hydroquinone coreactant [20,22], the more reactive tetrahydropyridine coreactant [20], the diiminoisoindoline route [23], the dimethaminoethanol route [23,24] and the lithium amylalkoxide route [25] were unsuccessful. The first four methods were totally ineffective and have not previously been reported to be effective for 3,6-disubstituted phthalonitriles.…”

Section: Methodsmentioning

confidence: 99%

Oligooxyethylene liquid phthalocyanines

Snow

Shirk

Pong

2000

J. Porphyrins Phthalocyanines

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A series of methyl-terminated oligooxyethylene ( CH 3( OCH 2 CH 2)n O , n = 8.8)-substituted phthalocyanines with peripheral substitution at four β positions, at four α positions and at the eight α positions was synthesized and structurally characterized. These compounds are isotropic liquids above 10 °C. Non-linear optical properties of the tetra-α- and tetra-β-substituted compounds were examined. Both are reverse saturable absorbers in the visible region of the spectrum, but the tetra-α-substituted compound has the larger non-linear absorption coefficient and can be a useful optical limiter in cases where a non-volatile liquid is desirable.

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“…Previous researchers designed and synthesized a wide variety of phthalonitrile monomers to alleviate the problem [20][21][22]. The curing reaction of these phthalonitrile monomers was assisted by a series of curing agents, such as transition metal, transition metal salts [23], organic amine [24], and phenols [25]. Nevertheless, the vast majority of the curing 2 of 15 agent has inferior thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Novolac/Phenol-Containing Phthalonitrile Blends: Curing Characteristics and Composite Mechanical Properties

Zhang

Wang

et al. 2020

Polymers

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The phenol-containing phthalonitrile resin is a kind of self-curing phthalonitrile resin with high-temperature resistance and excellent properties. However, the onefold phthalonitrile resin is unattainable to cured completely, and the brittleness of the cured product is non-negligible. This paper focuses on solving the above problems by blending novolac resin into phenol-containing phthalonitrile. Under the action of abundant hydroxyl group, the initial curing temperature and gelation time at 170 °C decrease by 88 °C and 2820 s, respectively, monitored by DSC and rheological analysis. FT-IR spectra of copolymers showed that the addition of novolac increased the conversion rate of nitrile. When the novolac mass fraction is 10%, the peak of nitrile group disappears, which means the complete reaction. The mechanical test of blends composites shows that the maximum fracture strain of 10 wt% novolac addition is 122% higher than those of neat phthalonitrile composites on account of the introduction of flexible novolac chain segments. The mechanical properties are sensitive to elevated post-cured temperature; this is consistent with the result of morphological investigation using SEM. Finally, the dynamic mechanical analysis indicated that the glass transition temperature heightened with the increase of novolac content and post-curing temperature.

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Polymerization of Bisphthalonitriles: Metal Free Phthalocyanine Formation

Cited by 17 publications

References 0 publications

Metallophthalocyanine dimers incorporating five-atom covalent bridges

Metallophthalocyanine dimers incorporating five-atom covalent bridges

Oligooxyethylene liquid phthalocyanines

Novolac/Phenol-Containing Phthalonitrile Blends: Curing Characteristics and Composite Mechanical Properties

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