- Metal-free phthalocyanine single crystal: Solvothermal synthesis and near-infrared electroluminescence
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A metal-free purple H2Pc single crystal was synthesized by a facile solvothermal method, and its solubility and near-infrared (NIR) optical properties were also investigated due to its potential applications as a light-emitting layer for OLEDs. The H2Pc single crystal is insoluble in 1-chlorine naphthalene and other organic solvents. It gives a wide absorption in the range from 620 nm to 679 nm and a wide emission in near 922 nm. As an active light-emitting layer, H2Pc was employed to fabricate electroluminescent (EL) devices with a structure of ITO/NPB (30 nm)/Alq3:H2Pc (30 nm)/BCP (20 nm)/Alq3 (20 nm)/Al. The emission center is at 936 nm when the H2Pc doping concentration is 20 wt%. The doping concentration strongly governs the emission intensity. When doping concentration decreases from 10 wt% to 1 wt%, the emission intensity remarkably fades, and simultaneously the emission center undergoes a blue shift.
- Bai, Qing-Long,Zhang, Chun-Hua,Song, Juan-Juan,Liu, Jing-Hai,Feng, Yan-Chun,Duan, Li-Mei,Cheng, Chuan-Hui
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- Direct Synthesis of τ-Form Metal-Free Phthalocyanine from Phthalodinitrile by Seeding Procedure
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Direct synthesis of τ-form metal-free phthalocyanine (τ-H2Pc) was performed from phthalodinitrile by using of 1,8-diaza-bicyclo(5,4,0)undecene-7 (DBU) and crystal nucleus in alcohol.The yield of τ-H2Pc was investigated under various conditions.
- Enokida, Toshio,Ehashi, Shigeyuki
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- Deformed phthalocyanines: Synthesis and characterization of zinc phthalocyanines bearing phenyl substituents at the 1-, 4-, 8-, 11-, 15-, 18-, 22-, and/or 25-positions
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The synthesis of a series of zinc phthalocyanines partially phenyl-substituted at the 1-, 4-, 8-, 11-, 15-, 18-, 22-, -and/or 25-positions (the so-called α-positions) is reported. Macrocycle formation based on 3,6-diphenylphthalonitrile, o-phthalonitrile,
- Fukuda, Takamitsu,Homma, Shigetsugu,Kobayashi, Nagao
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- Synthesis of Novel Unsymmetrical Monoaminated Phthalocyanines
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Metal-free monoaminophthalocyanine 3 was synthesised by reacting of subphthalocyanine 1 with 5-amino-1,3-diiminoisoindoline 2.Alternatively, compound 3 was prepared from octadecylaminodiiminoisoindoline 6 by reaction with 1 to give 7 followed by acidic hydrolysis.The zinc complex 8 was obtained from 3 by treatment with anhydrous zinc acetate.The preparation of 8 by template condensation of subphthalocyanine 1 with aminodiiminoisoindoline 2 and zinc acetate was unsuccessful.In this case, a mixture of statistical distribution compounds was obtained.A tentative reaction pathway for the condensation between subphthalocyanines and diiminoisoindolines is also given.
- Sastre, Angela,Torres, Tomas,Hanack, Michael
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- Mutual effects of equatorial and axial ligands on the stability of praseodymium(III) and samarium(III) phthalocyanine complexes
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The nature of axial ligand in lanthanide(III) phthalocyanine complexes markedly affects their physicochemical properties. The role of axially coordinated anion in the stability of coordination sphere was determined by the example of praseodymium(III) and samarium(III) phthalocyanine complexes (X)LnPc (X = Cl-, Br-, AcO-). The synthesis and the results of dissociation kinetics study of the complexes under the action of AcOH in ethanol solution were presented. Stability parameters for the complexes, kinetic equations, and activation parameters for the dissociation of coordination centers were determined. Effect of the axial ligand on the strength of macrocycle binding and the stoichiometric mechanism of complex dissociation reaction was considered. The state of axial bond in the complexes was shown to determine the value of reaction order toward acid (1 or 2) and the nature of rate-limiting step of the reaction: with participation of molecule or ionized in the axial direction complex.
- Lomova
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- An efficient two-step synthesis of metal-free phthalocyanines using a Zn(ii) template
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A new family of cationic phthalocyanines containing four guanidinium groups was synthesized in pyridine-HCl at 120 °C; under these conditions zinc was removed from both the starting materials and products to reveal a new synthetic route to metal-free phth
- Alzeer, Jawad,Roth, Phillipe J. C.,Luedtke, Nathan W.
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- Synthesis of non-substituted phthalocyanines by standard and non-standard techniques. Influence of solvent nature in phthalocyanine preparation at low temperature by UV-treatment of the reaction system
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Several synthetic techniques for metal-free phthalocyanines (Pc) and d- and f-metal phthalocyaninates ("PcM") starting from different precursors (phthalonitrile, urea and phthalic anhydride, phthalimide, phthalic acid, etc.) are reviewed. Conventional methods are presented, as well as some less well-known techniques such as those using ultrasound, laser, microwaves, or nuclear transformation. Special attention is paid to phthalocyanine formation at relatively low temperatures (0-60 °C). Experimental results on Pc formation using UV-irradiation of the reaction system are presented. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
- Kharisov,Ortiz Mendez,Almaraz Garza,Almaguer Rodriguez
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- Synthesis of metal-free phthalocyanines in functionalized ammonium ionic liquids
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A convenient, fast, efficient, and ecofriendly synthesis of metal-free phthalocyanines from various substituted phthalonitriles in different hydroxyalkylammonium ionic liquids in the presence of 1,8-diazabicyclo-[5,4,0]- undec-7-ene (DBU) is reported in moderate yields. The effect of concentration of DBU and temperature on the synthesis of phthalocyanine in N-(2-hydroxyethyl)-N, N-dimethylbutylammonium bromide ionic liquid has been examined, and the ionic liquid has been recovered and reused conveniently. Copyright Taylor & Francis Group, LLC.
- Chauhan,Agarwal, Shweta,Kumari, Pratibha
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- Synthesis and characterization of a phthalocyanine-porphyrazine hybrid and its palladium(II) complex
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A phthalocyanine-porphyrazine hybrid molecule composed of three phthalonitrile units and one maleonitrile moiety was prepared by cyclomerization of the reactants in the presence of magnesium butoxide. Two thioether groups fused to β-pyrrol positions were complexed with PdCl2. The compounds were characterized by 1H NMR, IR, and UV/Vis spectroscopy as well as elemental analysis.
- Sesalan, Sebnem B.,Guel, Ahmet
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- Mutual influence of ligands and reactivity of Gd and Dy acidophthalocyaninate complexes
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The results of the kinetic study of dissociation of Gd(III) and Dy(III) complexes with phthalocyanine of the composition (X)LnPc (X is single-charged acido ligand) with isolation of macrocyclic ligand depending on the temperature, composition of mixed eth
- Lomova,Andrianova
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- 3,6-didecyloxyphthalonitrile as a starting compound for the selective synthesis of phthalocyanines of the ABAB type
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Reactions of 3,6-dipentyloxy-and 3,6-didecyloxyphthalonitriles with lithium pentoxide in pentan-1-ol were studied. 3,6-Didecyloxyphthalonitrile can be used for the preparation of both the corresponding octasubstituted phthalocyanines and phthalocyanines of the ABAB type.
- Kudrik,Nikolaev,Shaposhnikov
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- Cerium-promoted formation of metal-free phthalocyanines
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Treatment of phthalonitriles with 6 mol% of CeCl3 or Ce(acac)3 (acac=acetylacetonate) in refluxing 1-pentanol affords the corresponding metal-free phthalocyanines in moderate yields. This non-alkaline pathway is complementary to the base-promoted cyclization methods which are commonly employed in the synthesis of phthalocyanines. Addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) greatly shortens the reaction time and increases the yield of these reactions.
- Lee, Chi-Hang,Ng, Dennis K.P
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- A green route to prepare metal-free phthalocyanine crystals with controllable structures by a simple solvothermal method
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Exploring the environmentally friendly and low-cost synthesis strategies of phthalocyanine (Pc) crystals in just one step is an absolute challenge. The solvothermal synthesis of phthalocyanine crystals shows the advantages of high-quality crystalline products, facile reaction and purification, and low cost. Nevertheless, only a few metal phthalocyanine crystals have been successfully synthesized via solvothermal reactions. In this study, we found that the crystalline β metal-free phthalocyanine needles could be directly prepared via the tetrapolymerization of phthalodinitrile catalyzed by DBU in solvothermal reactions. Similar to the preparation of β-phthalocyanine crystals, the α metal-free phthalocyanine crystals with the specific multiply-laminated structures can be obtained through solvothermal reactions assisted by DBN. SEM characterization showed that the individual β metal-free phthalocyanine has a well-defined quadrangular shape with smooth faces. However, the α metal-free phthalocyanine exhibits a distinctive undulating surface morphology. Both phthalocyanines showed satisfactory thermal stability (from room temperature to about 300 °C), excellent resistance to acid/alkali solution, and fast photoelectric response properties (order of magnitude of response time, 10-6 s) as tested by TG-DSC and TPV, respectively. It is noted that ethanol was used as the reaction medium and the resulting phthalocyanine crystals can be facilely purified using hot ethanol to dissolve the impurities adsorbed on the surfaces of phthalocyanine crystals. Compared to the traditional methods, no re-crystallization operation was carried out for our method. To the best of our knowledge, this is the first report on the solvothermal synthesis of metal-free phthalocyanine crystals with controllable crystal form adjusted by DBU/DBN in one step.
- Fa, Wenjun,Ge, Suxiang,He, Qin,Li, Dapeng,Li, Yun,Ma, Juntao,Sun, Guofu,Zhang, Peng
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p. 31226 - 31234
(2021/11/30)
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- DNA interaction and anticancer properties of new peripheral phthalocyanines carrying tosylated 4-morpholinoaniline units
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In this paper, tosylated 4-morpholinoaniline units fused peripherally tetra-substituted free-base (5), copper(II) (6), zinc(II) (7), cobalt(II) (8) and magnesium(II) (9) phthalocyanines (Scheme 1) were reported and these new phthalocyanine conjugates were characterized through Fourier Transform–Infrared (FT–IR) with ATR sampling accessory, Mass Spectra Analysis [Matrix Assisted Laser Desorption/Ionization–Time of Flight–Mass Spectral (MALDI–TOF–MS)] and Ultraviolet–visible (UV–vis) (for all new phthalocyanines), elemental analysis, as well as 1H and 13C NMR spectroscopic techniques [for the compounds (2), (4), (5), (7) and (9)]. The potential utilization of the new peripheral phthalocyanine compounds (7–9) as the new pharmaceutical agents in PDT applications (in oncology and molecular biology) were determined in aspects of pBR322 plasmid DNA cleavage on agarose gel electrophoresis. The results showed that compound (7) cleaved pBR322 plasmid DNA with irradiation. Compound (7) displayed hypochromism without any shift on the addition of increasing concentrations of ct-DNA and Kb of compound (7) was calculated as 2.45 ± (0.20) × 104 M?1. In photochemical studies, the ΦΔ value of compound (7) was determined as 0.11. The cytotoxic/phototoxic properties of compound (7) which had the best photocleavage effects among tested compounds were investigated using MTT assay toward human colorectal (HCT-116) and cervical (HeLa) cancer cells. The cell viabilities of compound (7) were found to be 73 ± 1.6% (HCT-116) and 65 ± 5.5% (HeLa) at 100 μM with irradiation.
- ?mero?lu, ?pek,?zel, Arzu,ünver, Yasemin,Barut, Burak,Durmu?, Mahmut,Ertem, Beytullah,Kantekin, Halit,Yal??n, Can ?zgür,Yalazan, Halise
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- Nanostructural catalyst: Metallophthalocyanine and carbon nano-onion with enhanced visible-light photocatalytic activity towards organic pollutants
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Metallophthalocyanine (MPc) and carbon nano-onion (CNO) derivatives were synthesized and characterized by using ultraviolet-visible spectroscopy, infrared and Raman spectroscopy, scanning electron microscopy with energy-dispersive X-ray spectroscopy and X-ray powder diffraction. The unmodified CNOs and MPc-CNO derivatives were used as photocatalysts for rhodamine B (RhB) degradation under visible-light irradiation. The photocatalytic studies revealed that the MPc-CNO nanostructural materials simultaneously exhibited a high absorption capacity and an excellent visible-light-driven photocatalytic activity towards RhB. These nanostructures possess great potential for use as active photocatalysts for organic pollutant degradation.
- Brzezinski, Krzysztof,Butsyk, Olena,Chaur, Manuel N.,Czyrko-Horczak, Justyna,Echegoyen, Luis,Olejnik, Piotr,Plonska-Brzezinska, Marta E.,Regulska, Elzbieta,Tomczykowa, Monika,Zubyk, Halyna
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p. 10910 - 10920
(2020/03/30)
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- Phthalocyanine gadolinium photosensitizer with multi-modal image navigation function, preparation method and applications thereof
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The invention discloses a phthalocyanine gadolinium photosensitizer with a multi-modal image navigation function, a preparation method and applications thereof, and belongs to the field of preparationof photodynamic drugs or photosensitizers, wherein the structural formula of the photosensitizer is represented by a formula (I). According to the invention, the photosensitizer is clear in structureand shows efficient singlet oxygen yield; the photosensitizer used for photodynamic therapy has the characteristics of simple preparation process, safety, environmental protection, good imaging effect and the like, wherein hydrophobic phthalocyanine gadolinium as an example can rapidly recognize and detect malignant tumors through MRI, photoacoustic imaging, photo-thermal imaging and the like andis enriched in the area; the phthalocyanine gadolinium photosensitizer can achieve nondestructive real-time dynamic detection and imaging of tumor lesion sites, performs multi-modal guided synchronous diagnosis and treatment in various joint modes, and has wide medical application prospect; and the photosensitizer can also be used for multi-modal imaging detection of cancer diagnosis on tissues and living bodies, so that the purpose of diagnosing while treating cancers is achieved.
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Paragraph 0106-0109
(2020/05/08)
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- A simple synthesis of symmetric phthalocyanines and their respective perfluoro and transition-metal complexes
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We report a simple synthesis protocol for making phthalocyanines (Pcs) starting from phthalonitriles. This method is general and requires no specialised equipment. The complexes are isolated and characterised using X-ray diffraction, NMR, FTIR and Raman spectroscopy and high-resolution mass spectrometry. First, we study and present a one-step synthesis route to a metal-free Pc (H2PcH16), as well as to the corresponding MPcH16 complexes of Mn, Fe, Co, Ni, Cu and Zn. Then, we show that this route can also be used to make the fluorinated Pc analogues (MPcF16). Finally, we present a new and useful procedure for inserting a metal ion into a metal-free H2PcH16 ring, by direct metalation, yielding the corresponding MPcH16 complex. This last method is especially useful if you want to make different MPcH16 complexes.
- Denekamp, Ilse M.,Veenstra, Florentine L.P.,Jungbacker, Peter,Rothenberg, Gadi
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- Solvothermal modification of magnesium phthalocyanine
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Reactivity of magnesium phthalocyanine (MgPc) in the dry 3,4-lutidine (3,4-lut), in the 3,4-lut/DMSO, in DMSO and in 3,4-lut/acetylacetone (acacH) systems has been investigated. Reaction of MgPc with dry 3,4-lut leads to formation of MgPc(3,4-lut) compoun
- Janczak, Jan
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- Synthesis, characterization and dielectric properties of novel metal oxide-phthalocyanine nanocomposites
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ORGANIC and metal-organic polymers which have electrical properties have opened up a promising field in material science and engineering. Phthalocyanine (H2Pc) and metal oxide-phthalocyanine (MO-Pc) where (MO = ZnO, NiO, FeO and CoO) were prepared by urea fusion technique. The prepared composites were identified by means of Fourier transform infrared spectroscopy (IR) and X-ray diffraction (XRD). The XRD data indicate that the ZnO-Pc and NiO-Pc are highly crystalline and particle sizes are ranged from 28.4 to 57.2 nm and from 51.4 to 82.9 respectively. The dielectric properties including dielectric constant ?' and dielectric loss ?'' of the prepared composites were calculated from the experimental capacitance values in the frequency range 100 Hz to 5MHz and in the temperature range of 25oC to 120oC. Generally, ?' are found to be decreased with increasing frequency and increase with increasing temperature. It is obvious that, appearance of peak for each MO in the dielectric loss suggests the presence of relaxing dipoles in the MO-Pc nanocomposites. The relaxation time τ, activation enthalpy ΔH and the entropy change ΔS of the prepared composites were calculated. The obtained data were correlated to the nature of doping metal oxide.
- Salama,Abdel-Karim
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p. 259 - 272
(2018/06/15)
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- PEG-containing ruthenium phthalocyanines as photosensitizers for photodynamic therapy: Synthesis, characterization and in vitro evaluation
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Three ruthenium(ii) phthalocyanines functionalized at their axial positions with 4-12 PEG chains bearing hydroxy, amino and ether terminal groups were synthesized and studied as PDT agents against bladder cancer cells. All three dyes displayed high singlet oxygen generation quantum yields in DMSO (ΦΔ = 0.76). The water-soluble Ru(L3)2Pc also shows high singlet oxygen quantum yields (ΦΔ = 0.48) in neat water. In vitro studies show that these complexes are accumulated in bladder cancer cells, are nontoxic PSs per se, and have high phototoxic efficiency.
- Teles Ferreira, Joana,Pina, Jo?o,Alberto Fontes Ribeiro, Carlos,Fernandes, Rosa,Tomé, Jo?o P. C.,Rodríguez-Morgade, M. Salomé,Torres, Tomás
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p. 5862 - 5869
(2017/08/04)
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- ORGANIC COMPOUND, CHARGE-TRANSPORTING MATERIAL, AND ORGANIC ELECTROLUMINESCENT ELEMENT
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There are provided an organic having both excellent hole transporting property and satisfactory electron transporting and showing excellent durability against electric oxidation/reduction and a high triplet excitation level, and a charge transporting material and an organic electroluminescent device each using the organic compound. The organic compound is represented by following Formula (I): wherein Cz 1 and Cz 2 each represent a carbazolyl group; Z represents a direct bond or an arbitrary linkage group enabling the conjugation of nitrogen atoms in the carbazole rings of Cz 1 and Cz 2 with each other; and Q represents a direct bond connecting to "G" in following Formula (II): wherein Ring B 1 represents a six-membered aromatic heterocyclic ring having "n" nitrogen atom(s) as hetero atom(s); "n" represents an integer of from 1 to 3; G represents a direct bond or an arbitrary linkage group connecting to Q when G connects to Q; Gs connect to carbon atoms at the ortho-position and the para-position with respect to nitrogen atom(s) in Ring B 1 ; G represents an aromatic hydrocarbon group when G does not connect to Q; and "m" represents an integer of from 3 to 5.
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- Facile synthesis of phthalocyanine at low temperature with diisopropylamide anion as nucleophile
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Abstract Phthalocyanine has been synthesized from phthalonitrile and lithium diisopropylamide (LDA) at ambient or even lower temperatures. In this novel, facile, and low reactant-consuming method, diisopropylamide anions work as nucleophile to initiate the low temperature reaction. The mechanism has been rationalized by density functional theory (DFT) calculation. Our method is also useful for the transformation of some phthalonitrile derivatives to phthalocyanine compounds.
- Zheng, Wei,Wan, Cheng-Zhang,Zhang, Jing-Xuan,Li, Cheng-Hui,You, Xiao-Zeng
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supporting information
p. 4459 - 4462
(2015/06/30)
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- Toner and toner production method
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The present invention provides a toner having superior color development property and a method of producing a toner having favorable particle size distribution and color development property, in which the toner containing a binder resin and a colorant that contains a phthalocyanine pigment represented by general formula (1), and the method for producing the toner.
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(2014/03/24)
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- Convenient and efficient method for the synthesis of phthalocyanines and metallophthalocyanines in task-specific 2-hydroxyethyl ionic liquids
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Tetramerization of substituted phthalonitriles in task-specific 2-hydroxylethyl-based imidazolium and ammonium ionic liquids at 100 °C gave corresponding phthalocyanines in moderate yield. Further the reaction of substituted phthalonitriles in the presence of transition-metal salts in ionic liquids gave the corresponding metallophthalocyanines. The 2-hydroxylethyl ammonium ionic liquids gave better yields of phthalocyanines than 2-hydroxylethyl imidazolium and nonhydroxyl functionalized ionic liquids. The isolation and separations of different phthalocyanines were accomplished by silica-gel column chromatography, and products were characterized by various spectroscopic techniques.
- Yadav, Kumar Karitkey,Poonam,Chauhan, Shive M. S.
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supporting information
p. 2797 - 2807
(2014/10/15)
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- Synthesis and properties of 172-phenyl-5,10,15,20- tetraazatribenzo[b,g,l]pyrazino[2,3-q]porphyrin-173(17 4H)-one
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172-Phenyl-5,10,15,20-tetraazatribenzo[b,g,l]pyrazino[2,3-q] porphyrin-173(174H)-one was synthesized for the first time by template cyclotetramerization of 5,7-diphenyl-6H-1,4-diazepine-2,3- dicarbonitrile with phthalonitrile. Its complexation with zinc(II) acetate followed a bimolecular mechanism. Acid-base properties of the resulting zinc complex in benzene-acetic acid were studied, and the stability constant of its monoprotonated (at the meso-nitrogen atom) form was determined.
- Malyasova,Kokareva,Tarakanov,Aleksandriiskii,Khelevina,Koifman
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p. 1812 - 1818
(2014/08/05)
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- Gold(II) phthalocyanine revisited: Synthesis and spectroscopic properties of gold(III) phthalocyanine and an unprecedented ring-contracted phthalocyanine analogue
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In 1965, gold(II) phthalocyanine (AuPc, 1) was described to be synthesized from unsubstituted 1,3-diiminoisoindoline and gold powder or AuBr. Compound 1 has been regarded as a rare example of a paramagnetic gold(II) complex. However, its chemistry, especially the oxidation state of the central gold ion, has not been previously explored due to the inherent insolubility of 1 caused by its unsubstituted structure. In our attempt to synthesize soluble AuPcs by using 5,6-di-substituted 1,3-diiminoisoindolines, gold(III) phthalocyanine chloride (3) and a gold(III) complex of an unprecedented ring-contracted phthalocyanine analogue ([18]tribenzo-pentaaza-triphyrin(4,1,1), 4) were isolated. With this discrepant result from the original literature in hand, a reinvestigation of the original AuPc synthesis by using unsubstituted 1,3-diiminoisoindoline and various gold salts (including gold powder and AuBr) was performed, finding that only unsubstituted analogues of 3 and 4 or free-base phthalocyanine were obtained. Copyright
- Wong, Edwin W. Y.,Miura, Akito,Wright, Mathew D.,He, Qi,Walsby, Charles J.,Shimizu, Soji,Kobayashi, Nagao,Leznoff, Daniel B.
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supporting information
p. 12404 - 12410
(2013/01/14)
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- PREPARATION AND USES OF GUANIDINIUM-MODIFIED PORPHYRINS AND PHTHALOCYANINES
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The invention relates to porphyrins, porphyrazines and phthalocyanines carrying a guanidine substituent. These compounds are obtained by treating a porphyrin, porphyrazine or phthalocyanine, respectively, carrying an amino substituent with cyanamide or a carbodiimide in an ionic liquid at elevated temperature. Described are valuable diagnostic, photoelectronic, and therapeutic uses, e.g. as photosensitizing agents in photodynamic therapy, fluorescent and magnetic probes for diagnosis, or to transport other molecules through the plasma membranes of living cells. Furthermore, the present invention relates to a method of removing a metal from metalloporphyrins, metalloporphyrazines and metallophthalocyanines by heating the zinc(II)-containing compounds in an ionic liquid and a proton source at temperatures between 60°C and 200°C.
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Page/Page column 24
(2010/04/06)
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- Phthalocyanine dyes and their preparation and use
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Phthalocyanine dyes of general formula (II) and, in particular, of general formula (III) wherein R1-R8, R9-R12, Me, M, m, n, o and p are as described in the specification, are excellent photosensitizers for the preparation of pharmaceutical compositions for photodynamic therapy or photo diagnostics.
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- Lanthanide triiodide-catalyzed amination of phthalonitrile. the structure of 1-isopropylamino-3-(isopropylimino)isoindole
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The reactions of phthalonitrile with MeNH2, Pr nNH2, and PriNH2 in the presence of catalytic amounts of LnI3 (Ln = Nd or Dy) or LnI3(THF) 3 (Ln = Gd or Nd) afford 1,3-
- Bochkarev,Balashova,Maleev,Pestova,Fukin,Baranov,Kurskii, Yu. A.
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experimental part
p. 2162 - 2167
(2010/05/02)
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- Soluble precursors of 2,3-naphthalocyanine and phthalocyanine for use in thin film transistors
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Soluble precursors of 2,3-naphthalocyanine (Nc) and phthalocyanine (Pc) were prepared and were converted into insoluble semiconducting thin films of Pc and Nc by heating after fabrication via spin-coating. The Royal Society of Chemistry.
- Hirao, Atsuko,Akiyama, Taiji,Okujima, Tetsuo,Yamada, Hiroko,Uno, Hidemitsu,Sakai, Yoshimasa,Aramaki, Shinji,Ono, Noboru
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scheme or table
p. 4714 - 4716
(2009/03/12)
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- Energy transfer in zinc porphyrin-phthalocyanine heterotrimer and heterononamer studied by fluorescence resonance energy transfer (FRET)
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Two or eight zinc triphenyl porphyrins were conjugated with Zn-phthalocyanine or H2-phthalocyanine to form ZnPc-(ZnTPP)2, ZnPc-(ZnTPP)8, H2Pc-(ZnTPP)2 and H2Pc-(ZnTPP)8. Energy t
- Durmus,Chen,Zhao,Nyokong
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- Novel and mild route to phthalocyanines and 3-iminoisoindolin1-ones via N,N-diethylhydroxylamine-promoted conversion of phthalonitriles and a dramatic solvent-dependence of the reaction
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Refluxing a mixture of phthalonitrile C6R1R 2R3R4(CN)2 1 (R1-R 4 = H), or its substituted derivatives 2 (R1, R 3, R4 = H, R2 = Me), or 3 (R1, R4 = H, R2, R3 = Cl) (lequiv.) and N,N-diethylhy-droxylamine, Et2NOH, (4 equivs.) in methanol for 4 h results (Route A) in precipitation of the symmetrical (6 and 8) and an isomeric mixture of unsymmetrical (7) phthalocyanines, isolated in good (55-65 % ) yields. The reaction of phthalonitriles 1, 2, or 4 (R1, R 3, R4 = H, R2 = NO2) (4 equivs.) with Et2NOH (8 equivs.) in the presence of a metal salt MCl 2 (M = Zn, Cd, Co, Ni) (1 equiv.) in n-BuOH or without solvent results in the formation of metallated phthalocyanine species (9-17). Upon refluxing in freshlydistilled dry chloroform, phthalonitrile 1 or its substituted analogues 2, 3 or 5 (R1-R4 = F) (1 equiv.) react with N,N-diethylhydroxylamine (2 equivs.) affording 3-iminoisoindolin-1- ones 18-21 (Route B) isolated in good yields (55-80%). All the prepared compounds were characterized with C, H, and N elemental analyses, ESI-MS, IR, and compounds 18-21 also by ID (1H, 13C(1H]), and 2D (1H,15N-HMBC and 1H,13CHMQC, 1H,13C-HMBC) NMR spectroscopy.
- Luzyanin, Konstantin V.,Kukushkin, Vadim Yu.,Kopylovich, Maximilian N.,Nazarov, Alexey A.,Galanski, Markus,Pombeiro, Armando J. L.
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p. 135 - 142
(2009/04/07)
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- Synthesis and spectroscopic properties of low-symmetry tribenzoporphyrazines with annulated 6H-1,4-diazepine ring
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Template co-condensation of 2,3-dicyano-5,7-diphenyl-6H-1,4-diazepine 1 with 10-fold molar excess of phthalodinitrile 2 in the presence of Mg II propoxide or butoxide in the corresponding alcohol leads to a mixture of MgII-diazepinoporphyrazines 3?6 from which the low symmetry 3:1 species 3, which contains three annulated benzene and one 1,4-diazepine rings, is separated by column chromatography as the aquo complex, [2,4-diphenyltribenzo[b,g,l][1,4]diazepino[2,3-q]porphyrazinato(aquo) magnesium(ii)], [Bz3DzPzMg(H2O)]. The complex 3 can be demetalated in acetic or trifluoroacetic acids under mild conditions with formation of the corresponding free-base [Bz3DzPzH2] 3a. This latter is also formed by co-cyclotetramerization of the same precursors 1 and 2 in the presence of sodium ethoxide in ethanol or lithium butoxide in butanol followed by demetalation of the intermediate disodium or dilithium salts in acid medium. The constitution and structure of the obtained compounds were established on the basis of elemental analysis, mass spectrometry, and 1H NMR spectra. The variable temperature 1H NMR measurements provide evidence that in porphyrazines 3 and 3a the 1,4-diazepine ring exists predominantly in the 6H-form over a wide temperature range. The free energy of activation for the inversion of the 1,4-diazepine ring determined for 3 is 45.6 ± 1.7 kJ mol?1. Solution UV-visible spectra measurements in acidic media (CH2Cl2/CF3COOH) provide evidence that the MgII complex 3 is easily protonated on the meso-N atom of the porphyrazine macrocycle followed by slow demetallation with formation of the free base 3a in its neutral form or as a species protonated on the diazepine ring. CSIRO 2008.
- Donzello, Maria Pia,Ercolani, Claudio,Mannina, Luisa,Viola, Elisa,Bubnova, Alena,Khelevina, Ol'ga G.,Stuzhin, Pavel A.
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p. 262 - 272
(2008/09/20)
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- (Phthalocyaninato)copper(II) complexes fused with different numbers of 15-crown-5 moieties - Synthesis, spectroscopy, supramolecular structures, and the effects of substituent number and molecular symmetry
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Symmetrical (phthalocyaninato)copper(II) complexes Cu(Pc′) [Pc′ = Pc(15C5), Pc(opp-15C5)2, Pc(adj-15C5)2, Pc(15C5) 3; Pc = unsubstituted phthalocyaninate, Pc(15C5) = 2,3-(15-crown-5)phthalocyaninate, Pc(opp-15C5)2 = 2,3,16,17-bis(15-crown-5)phthalocyaninate, Pc(adj-15C5)2 = 2,3,9,10-bis(15-crown-5)phthalocyaninate, Pc(15C5)3 = 2,3,9,10,16,17-tris(15-crown-5)phthalocyaninate] (2-5) have been prepared by the reaction of corresponding heteroleptic bis(phthalocyaninato)europium complexes Eu(Pc)(Pc′) [Pc′ = Pc(15C5), Pc(opp-15C5)2, Pc(adj-15C5)2, Pc(15C5)3, Pc(15C5)4; Pc = unsubstituted phthalocyaninate] with Cu(OAc)2 in dry dmf at 100°C. For the purpose of comparative studies, the symmetrical counterparts CuPc (1) and CuPc(15C5)4 [Pc(15C5)4 = 2,3,9,10,16,17,24, 25-tetrakis(15-crown-5)phthalocyaninate] (7) have also been prepared. These monomeric complexes have been characterized by spectroscopic methods in addition to elemental analysis. Having a series of closely related phthalocyanines with a different number and/or disposition of 15-crown-5 groups at the peripheral positions, the effects of 15-crown-5 substituent number and molecular symmetry on the electronic absorption spectra, infra-red (IR) spectra, and supramolecular structure formation induced by K+ ions have been investigated. Systematic studies on the formation of dimeric supramolecular structures of the series of monomers 2-6 reveal and confirm the previously proposed two-step three-stage process of K+-induced dimerization of phthalocyanines with three or four 15-crown-5 moieties. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Sheng, Ning,Zhang, Yuexing,Xu, Hui,Bao, Meng,Sun, Xuan,Jiang, Jianzhuang
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p. 3268 - 3275
(2008/02/10)
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- Efficient synthesis of transition-metal phthalocyanines in functional ionic liquids
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The synthesis of transition-metal phthalocyanines by the reaction of substituted and unsubstituted phthalonitriles in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and metal salts in functional imidazolium, pyridinium and ammonium ionic liquids at 100-140°C, is reported. The best yields of metallated phthalocyanines were achieved in butyl(2-hydroxyethyl)dimethylammonium bromide ionic liquid. Metallation of free-base phthalocyanines with different metal salts in the above ionic liquid has also been achieved in good yields. Georg Thieme Verlag Stuttgart.
- Chauhan,Kumari, Pratibha,Agarwal, Shweta
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p. 3713 - 3721
(2008/09/19)
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- Synthesis and spectral properties of 1,2,5-thiadiazolo-, 1,2,5-selenadiazolo-, and benzo-fused β-phenyl-substituted porphyrazines
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Cross cyclotetramerization of trans-2,3-diphenylbutanedinitrile with 1,2,5-thia(selena)diazole-3,4-dicarbonitriles or phthalodinitrile in the presence of magnesium butoxide gave mixtures of Mg(II) porphyrazine complexes which were treated with trifluoroac
- Stuzhin,Pimkov,Ul'-Khak,Ivanova,Popkova,Volkovich,Kuz'Mitskii,Donzello
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experimental part
p. 1854 - 1863
(2009/09/29)
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- COMPOUND, CHARGE TRANSPORT MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE
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An object of the invention is to provide a charge transporting material having an excellent heat resistance, excellent filming properties, an excellent charge transporting ability, and excellent light-emitting characteristics and, also, to provide an organic electroluminescent element providing a high luminance and a highly luminous efficiency and having a long life. The invention relates to a charge transporting material comprising a compound having within the molecule two or more pyridine rings substituted at 2-, 4- and 6-positions thereof, which rings do not substantially conjugate each other (provided that the 3- and 5-positions of the pyridine rings may be substituted) and an organic electroluminescent element using the charge transporting material.
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- Reactions of ferrocene with phthalonitrile on the surface of oxide powders
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The reaction of ferrocene with phthalonitrile at 200°C in a vacuum in the absence of solvents forms crystals of the monoclinic phthalocyanine β phase and ferrocene polymerization products. The use of oxide powders (SiO 2, V2O5) as a surface for the reaction of ferrocene with phthalonitrile makes it possible to obtain iron phthalocyanines. The samples of pure compounds and deposited phthalocyanine complexes were analyzed by electronic absorption and IR spectroscopy, and X-ray diffraction. Pleiades Publishing, Inc., 2006.
- Suvorova,Verle,Bazyakina,Kutyreva,Makarov,Shchupak
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p. 649 - 653
(2008/02/08)
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- Use of zeolites for phthalocyanine synthesis at low temperature
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Non-substituted phthalocyanines have been synthesised starting from phthalonitrile in various non-aqueous solvents in the presence of two different zeolites of the clinoptilolite type is studied. The zeolites are shown to be effective matrices for phthalonitrile cyclisation at relatively low temperatures (0-40°C).
- Kharisov, Boris I.,Medina,De La Rosa, Javier Rivera,Mendez, U. Ortiz
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p. 404 - 406
(2007/10/03)
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- The synthesis of metal-free phthalocyanines from phthalonitriles with hexamethyldisilazane
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Metal-free phthalocyanines were prepared in good yields by heating phthalonitriles with hexamethyldisilazane, (NH4)2SO 4, and DMF. Good yields of metal-free phthalocyanines involving peripherally substituted phthalocyanines were attained with a catalytic amount of hexamethyldisilazane. Naphthalocyanine was also prepared. Additional additives were examined to accelerate the formation of the phthalocyanine framework.
- Uchida, Hitoshi,Yoshiyama, Hideyuki,Reddy, Paidi Yella,Nakamura, Shuichi,Toru, Takeshi
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p. 1401 - 1404
(2007/10/03)
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- An efficient synthesis of phthalocyanines based on an unprecedented double-addition of oximes to phthalonitriles
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A novel and efficient method is reported for the preparation of phthalocyanines from phthalonitrile or its derivatives which utilizes low-cost reagents of hydrolytic stability, high simplicity, and easy accessibility, i.e., oximes, and proceeds via an unprecedented double addition of oximes to the nitrile group. Copyright
- Kopylovich, Maximilian N.,Kukushkin, Vadim Yu.,Haukka, Matti,Luzyanin, Konstantin V.,Pombeiro, Armando J. L.
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p. 15040 - 15041
(2007/10/03)
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- Substituted metal-phthalocyanines, their preparation and the use thereof
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The present invention is directed tometal-phthalocyanines of general formula (I) to the corresponding conjugates, the processes for their preparation and use in the photodynamic therapy of microbial infections (viral, bacterial and mycotic), tumor, pre-cancerous and proliferative pathologies and/or in the diagnosis, as well as for blood and blood derivatives sterilization.
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- Beta-cyclodextrin dimers and phthalocyanines and uses thereof
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The invention provides β-cyclodextrin dimers and phthalocyanines which can be used in photodynamic therapy of cancer.
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- Synthesis and Characterisation of Unsymmetrical Porphyrazines Containing Bis(hydroxyethylthio) Substituents
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Unsymmetrical porphyrazines bearing a single peripheral bis(hydroxyethylthio) moiety were synthesised by mixed condensation of bis(2-hydroxyethylthio)maleonitrile and phthalonitrile. Complexation of the thioether groups of metal-free porphyrazine with PdCl2 further lowered the intensity of the Q-band absorption of the porphyrazine core. The new compounds were characterised by elemental analyses, IR, 1H NMR, UV-Vis, and mass spectra.
- Kalkan, Ayfer,Bayir, Zehra A.
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p. 1555 - 1560
(2007/10/03)
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- Novel Synthesis of Metal-Free Phthalocyanines from Phthalimides and Phthalic Anhydrides with Hexamethyldisilazane
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Metal-free phthalocyanines and their peripherally substituted derivatives have been synthesized from unsubstituted and substituted phthalimides, phthalic anhydrides, and naphthalimide on heating with hexamethyldisilazane under mild conditions.
- Uchida, Hitoshi,Yoshiyama, Hideyuki,Reddy, Paidi Yella,Nakamura, Shuichi,Toru, Takeshi
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p. 2083 - 2085
(2007/10/03)
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- Novel Efficient Preparative Method for Phthalocyanines from Phthalimides and Phthalic Anhydride with HMDS
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A convenient synthesis of peripherally substituted or unsubstituted phthalocyanines having a variety of metals is described. Phthalocyanines can be obtained by heating phthalimides or phthalic anhydride with metal salts, hexamethyldisilazane, a catalytic amount of p-TsOH, and DMF at 150 °C.
- Uchida, Hitoshi,Reddy, Paidi Yella,Nakamura, Shuichi,Toru, Takeshi
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p. 8736 - 8738
(2007/10/03)
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- Synthesis of phthalocyanines by microwave irradiation
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This invention provides a novel process for preparing soluble phthalocyanines by microwave irradiation in the absence of any organic solvent. Three different starting materials, i.e. t-butylphthalic anhydride, t-butyl phthalonitrile and metal-free H2Pc (tetra-t-butylphthalocyanine) have been adopted, respectively. The starting material with proper metal compound, such as chloride or acetate were irradiated in a commercial microwave oven for a period of 1 to 30 minutes at a power of 200?900 W. This process is noted to reduce drastically reaction time of MPc formation from 8?24 hours to 10?30 minutes due to its unique heating by microwave irradiation. Sandwiched type MPc2(such as Lu Pc2) can be produced only through metal replacement from metal-free phthalocyanine by microwave irradiation.
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- Phthalocyanines with peripheral siloxane substitution
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The present invention is phthalocyanine compounds with peripheral siloxane substitution, as well as methods for making these compounds and various uses thereof, having the basic structure: wherein —W—X—Y—Z are peripheral groups comprising individual W, X,
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- Use of long-wavelength electromagnetic radiation and photoprotective tumor localizing agents for diagnosis
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A process of pathology or target tissue identification comprising administering an imaging material to a pathology or target tissue bearing mammalian host and irradiating the mammalian host with electromagnetic radiation having a wavelength between about
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- Agglomerated pigment, process for producing the same, aqueous pigment dispersion, and water-based ink composition
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An agglomerated pigment comprises (1) an organic pigment compound, (2) either a sulfonated organic pigment compound obtained by incorporating at least one sulfonic group into the organic pigment compound or a sulfonated organic pigment derivative obtained by incorporating at least one sulfonic group into a derivative of the organic pigment compound, (3) univalent inorganic counter ions bonded to sulfonic groups of component (2), and (4) bivalent or higher inorganic counter ions which are bonded to sulfonic groups of component (2) and wherein each such group has an at least univalent positive charge, the surface of the agglomerated organic pigment as a whole being positively charged. An aqueous pigment dispersion and a water-based ink composition both having excellent storage stability, an agglomerated pigment for use as a raw material for the dispersion, and a process for producing the pigment are provided.
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- The solid phase, room-temperature synthesis of metal-free and metallophthalocyanines, particularly of 2,3,9,10,16,17,23,24-octacyanophthalocyanines
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Room-temperature synthesis of phthalocyanines (pcs) by condensation of phthalonitriles in the presence of solid sodium methoxide in THF is proposed for the synthesis of metal-free pcs with temperature- and/or base-sensitive substituents. The addition of metal salts after metal-free pc formation in the same vessel produces metallopcs in moderate to high (ca. 30-90%) yields.
- Nemykin, Victor N.,Kobayashi, Nagao,Mytsyk, Vladislav M.,Volkov, Sergey V.
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p. 546 - 547
(2007/10/03)
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