Synthesis of Phthalocyanines From Phthalonitrile With Organic Strong Bases

Tomoda, Haruhiko; Saito, Shôjirô; Ogawa, Shin-ichi; Shiraishi, Shinsaku

doi:10.1246/cl.1980.1277

Cited by 101 publications

(69 citation statements)

References 3 publications

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“…Since 4-hydroxyphthalonitrile (12) is unable to react with trityl chloride to give the corresponding ether and is unstable to basic conditions, 1 2 was treated with dimethoxymethane (13) or diethoxymethane (14) under acidic conditions (29) to give 4-methoxymethoxyphthalonitrile (15) and 4-ethoxymethoxyphthalonitrile (16) in 92 and 95% yield, respectively. 2,9,16,23-Tetra(methoxymethoxy)phthalocyaninato zinc(I1) (17) was prepared from 1 5 in 30% yield in a previous procedure (23), but similar treatment of 16 gave mostly decomposition products. When the improved procedure as described for 8 and 9 was used, compound 17 was prepared in 60% yield.…”

Section: Resultsmentioning

confidence: 99%

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The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines

Leznoff¹,

Hu²,

McArthur³

et al. 1994

Can. J. Chem.

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, 1990 (1994).2,9,16,23-Tetra-p-n-butylbenzyloxy-, 2,9,16,23-tetradiphenylrnethoxy-, 2,9,16,23-tetramethoxymethoxy-, and 1,8,15,22-tetra-p-n-butylbenzyloxyphthalocyanines were synthesized from the appropriate phthalonitriles. Metal-free phthalocyanines were converted to their zinc derivatives. Cleavage from the appropriate precursor with trifluoroacetic acid produced 2,9,16,23-tetrahydroxyphthalocyanine and 1,8,15,22-tetrahydroxyphthalocyanine and their zinc derivatives. NMR spectroscopy revealed that all the 2,9,16,23-tetrasubstituted phthalocyanines are the usual mixtures of the 2,9,16,23, 2,9,16,24, 2,9,17,24, and 2,10,16,24 isomers, but the two 1,8,15,22-tetrasubstituted phthalocyanines were formed as pure single isomers.CLIFFORD C. LEZNOFF, MOUGANG Hu, COLIN R. MCARTHUR, YONGNIAN Qn' l et JOHAN E. VAN LIER Can. J. Chem. 72, 1990.Utilisant les phtalonitriles approprits comme produits de dCpart, on a synthCtisC les 2,9,16,23-tCtra-p-n-butylbenzyloxy-, 2,9,16,23-tttraphtnylmCthoxy-, 2,9,16,23-tCtramtthoxym6thoxy-et 1,8,15,22-tttra-p-n-butylbenzyloxyphtalocyanines. On a transform6 les phtalocyanines libres de mttal en dCrivts zinciques. Le clivage du prtcurseur approprik avec de l'acide trifluoroacttique conduit h la 2,9,16,23-tttrahydroxyphtalocyanine et h la 1,8,15,22-tCtrahydroxyphtalocyanine et h leurs dCrivts zinciques. La RMN rtvttle que toutes les phtalocyanines tCtrasubstitu6es en 2,9,16,23 sont formCes des mClanges habituels des isombres 2,9,16,23, 2,9,16,24, 2,9,17,24 et 2,10,16,24; toutefois, les deux phtalocyanines substitu6es en 1,8,15,22 sont des isomkres purs.

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Section: Resultsmentioning

confidence: 99%

“…The precipitate was collected by centrifugation, and washed with water, methanol, and hexane. Further purification was performed in a flash silica gel column by eluting with THF and hexane (23). Evaporation of the solvent gave 0.557 g of a shining, blue solid in 65% yield.…”

Section: 91623-tetra(p-n-butylbenzyloxy)phthalocyani1ato Zinc(ii)mentioning

confidence: 99%

The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines

Leznoff¹,

Hu²,

McArthur³

et al. 1994

Can. J. Chem.

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“…1) was accomplished in n-amyl alcohol in the presence of strong base 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) at reflux temperature [22][23][24]. The metal phthalocyaninates (4-6) were obtained by using the anhydrous metal salts (NiCl 2 , Zn(O 2 CMe) 2 and CoCl 2 ) [25] (Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of di-n-hexylamino-substituted phthalocyanines

Gümüş

Ahsen

2002

J. Porphyrins Phthalocyanines

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Metal-free-and metallophthalocyanines (M = Ni, Zn and Co) carrying four din-hexylamino and four chloro groups in peripheral positions have been synthesized from the corresponding dichlorophthalonitrile derivative in the presence of the anhydrous metal salts [NiCl 2 , Zn(O 2 CMe) 2 , CoCl 2 ] or a strong organic base. The new compounds have been characterized by elemental analyses, IR, NMR and electronic spectroscopy and mass spectra.

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“…The statistical condensation is carried out by reacting equimolar amounts of tetraphenylphthalodinitrile (TPPN) (12) and the appropriate 2,3-dicyanonaphthalene 3,7,11 respectively with nickel acetate in hexanol in the presence of catalytic amounts of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) [17] at 145°C for 24 h. The mixtures of the obtained porphyrazinato nickel(II) complexes 13-15 are separated by common column chromatography on silica gel using a mixture of toluene/hexane as eluent. The sequence of eluation for all three series is a (BBBB) (only obtained in the case of series 13), b (ABBB), d (AABB), c (ABAB) and e (AAAB) (for the exact R f values see the experimental section).…”

Section: Synthesis Of the Benzonaphtho-condensed Porphyrazinato Nickementioning

confidence: 99%

Synthesis, Separation and Characterization of Naphthobenzo-condensed Porphyrazinato Nickel(II) Complexes

Polley

Linßen

Stihler

et al. 1997

J. Porphyrins Phthalocyanines

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Phthalocyanines and 2,3-naphthalocyanines are macrocyclic compounds which possess a variety of properties of potential importance in advanced technologies. The article discusses the influence of successive condensation of additional benzene rings to the phthalocyanine system. For this purpose three hexyloxy- and heptyl-substituted 2,3-dicyanonaphthalenes 3,7,11 and the respective 2,3-naphthalocyaninato nickel(II) complexes were prepared. In three statistical condensations of tetraphenylphthalodinitrile ( TPPN ) (12) and 2,3-dicyanonaphthalenes, 3,7,11, twelve unsymmetrical naphthobenzo-condensed porphyrazinato nickel(II) complexes 13b-15e were synthesized and separated by common column chromatography. All complexes were characterized by mass spectrometry, IR, UV and 1 H NMR spectroscopy.

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Synthesis of Phthalocyanines From Phthalonitrile With Organic Strong Bases

Abstract: In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene or 1,5-diazabicyclo[4.3.0]non-5-ene, metal-free phthalocyanine was obtained by heating phthalonitrile in alcohols. Addition of a copper(II) salt in the reaction gave copper phthalocyanine in a good yield.

Cited by 101 publications

References 3 publications

The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines

The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines

Synthesis and characterization of di-n-hexylamino-substituted phthalocyanines

Synthesis, Separation and Characterization of Naphthobenzo-condensed Porphyrazinato Nickel(II) Complexes

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