Purification and characterization of phthalocyanines

Wagner, Hans J.; Loutfy, Rafik O.; Hsiao, C. K.

doi:10.1007/bf00644652

Cited by 202 publications

(90 citation statements)

References 12 publications

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“…The resulting solid was filtered and washed with water. Train sublimation (35) of the crude material gave the imide 6 (3.98 g, 80%) as orange needles; mp 302-304°C (lit. (1 1 N-Phenyl-1,9-anthracenedicarboxylic imide (10) A suspension of 1,9-anthracenedicarboxylic acid (42) (4.50 g, 16.9 mmol) in 1-methyl-2-pyrrolidinone (180 mL) under nitrogen was heated to 125°C for 15 min to enable complete conversion to the anhydride.…”

Section: Methodsmentioning

confidence: 99%

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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Abstract:The reported structure of aceanthrene green, a pigment prepared by potassium hydroxide fusion of 1.9-anthracenedicarboxylic imide, was found to be incorrect. The structure of the pigment is reassigned to 7,8,15,16-dibenzo[a j]perylenetetracarboxylic diimide on the basis of COSY, NOESY, and inversion-recovery 'H NMR experiments. N-Alkyl-or N-phenyl-l,9-anthracenedicarboxylic imides, aceanthryleno[l,2-blquinoxaline, and a benzimidazole derivative of 1,9-anthracenedicarboxylic anhydride were found to give the same dibenzo[a jlperylene structure when reacted in potassium hydroxide. The electronic spectra of these derivatives is reported and it is shown that, as predicted by Pariser-Parr-Pople calculations, they absorb in the near-infrared. Finally, a mechanistic outline for the fusion is proposed on the basis of AM1 and frontier molecular orbital calculations.Key words: photoconductor, near-infrared, aceanthrene green, alkalifusion, polycyclic aromatic hydrocarbon.RCsumC : On a trouvC que la structure proposCe anterieurement pour l'ackanthrbne vert, un pigment prCparC par fusion de l'imide de l'acide anthracbne-l,9-dicarboxylique avec de l'hydroxyde de potassium, est incorrecte. En se basant sur des expkriences COSY, NOESY et d'inversion-rCcupCration en RMN du 'H on lui a rCattribuC la structure du diimide de l'acide dibenzo[a jlpCrylbne-7,8,15,16-tCtracarboxylique. On a trouvC que par rCaction, par fusion avec de l'hydroxyde de potassium, les N-alkyl-ou N-phCnylimides de l'acide anthrackne-1,9-di-carboxylique, l'acCanthrylCno[l,2-b]quinoxaline et un dCrivC benzimidazole de l'anhydride de l'acide anthracbne-l,9-dicarboxylique conduisent tous B la m&me structure dibenzo[a jlpCrylkne. On rapporte les spectres Clectroniques de ces dCrivCs et il est montrC, tel que prCdit par des calculs de type Pariser-Parr-Pople, qu'ils absorbent dans le proche infrarouge. Enfin, en se basant sur des calculs d'orbitales molCculaires AM1 et frontibres, on propose un aperp du mCcanisme pour la fusion.Mots cles : photoconducteur, proche infrarouge, acCanthrbne vert, fusion alcaline, hydrocarbure polycyclique aromatique.[Traduit par la rCdaction]

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Section: Methodsmentioning

confidence: 99%

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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“…24 Two types of substrates were used for the phthalocyanine deposition to induce different ordering of the molecules. 25 The first type is a c-plane sapphire or Si(110) substrate.…”

Section: Growthmentioning

confidence: 99%

Substrate-controlled ferromagnetism in iron phthalocyanine films due to one-dimensional iron chains

et al. 2012

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Using magneto-optical Kerr effect, SQUID magnetometry and magnetic circular dichroism spectroscopy, ferromagnetism was found below 4.5K in iron phthalocyanine thin films grown by molecular beam epitaxy. The stacking of the molecules can be controlled via deposition temperature and substrate choice. The molecules self-assemble such that quasi one-dimensional iron chains form. The chains are limited in length by the grain size or film thickness which is manipulated using judicious growth methods. Magnetic hysteresis loops show distinct features in the saturation magnetization and susceptibility that depend on the thin film structure and/or substrate. We find two regimes for the magnetic behavior: below temperatures of ∼ 25K, intra-chain interactions couple the Fe ions and produce non-traditional paramagnetic behavior, while at low temperatures below ∼ 4.5K interactions between the one-dimensional chains produce hysteresis, magnetic order, and slow magnetization dynamics.

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“…These materials were synthesized via thc reaction of perylene 3,4,9,1O-tetracarboxylic dianhydride with the desired amine. Products were purified by temperature gradient sublimation ( 10). The last compound (IV) is obtained as a mixture of two isomers shown in Fig.…”

Section: Mnterit11smentioning

confidence: 99%

Photoconductivity studies of perylene tetracarboxyl-diimides

Popović¹,

Loutfy²,

Hor³

1985

Can. J. Chem.

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This paper is dedicated to the 10th urlr~iver.sary of the Xerox ResetrrcIt Cetrtre of CurtutlnZORAN D. POPOVIC, RAFIK 0 . LOUTFY, and AH-MEE HOR. Can. J. Chem. 63, 134 (1985). Photoconductivity of a series of perylene tetracarboxyl-dimides has been studied by delayed-collection-field and electric field induced fluorescence quenching techniques. It has been shown that these materials exhibit both extrinsic (impurity controlled) and intrinsic carrier generation originating from the first excited singlet state. Perylene tetracarboxyl-diimides are photoactive in the visible spectral range and their carrier generation efficiencies compare well with generation efficiencies in the best known organic photoconductors. This makes them suitable for xerographic applications using visible light. ZORAN D. POPOVIC, RAFIK 0 . LOUTFY et AH-MEE HOR. Can. J. Chem. 63, 134 (1985). Faisant appel ii des techniques de piegeage de la fluorescence induite par un champ Clectrique et par un champ ii collection retardee, on a CtudiC la photoconductivitt d'une sCrie de perylenes tetracarboxyl-diimidcs. On montre que ces materiaux peuvent gCnCrer des transporteurs, h la fois d'une facon extrinseque (controlke par les impuretCs) et d'une facon intrinseque; ces propriCtCs auraient leur origine dans le premier Ctat singulet excite. Les pCryl6ncs tktracarboxyl-diimides sont photoactifs dans la region du visible et leurs efficacitks pour gCnCrcr des transporteurs se compare bien avec les efficacitts de generation des photoconducteurs organiques Ics mieux connus. On peut donc les considercr pour des applications xkrographiques utilisant de la lumikre visible.[Traduit par le journal]

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Purification and characterization of phthalocyanines

Cited by 202 publications

References 12 publications

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Substrate-controlled ferromagnetism in iron phthalocyanine films due to one-dimensional iron chains

Photoconductivity studies of perylene tetracarboxyl-diimides

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