147-14-8

Basic information

• Product Name: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper
• Synonyms: Copper, [29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32]-, (SP-4-1)- Copper, [phthalocyaninato(2-)]-;phthalocyanine blueB15:0;Pigment Blue 15 (purified by sublimation);Copper(II) Phthalocyanine (alpha-form);Copper(II) Phthalocyanine (beta-form);Copper(II) phthalocyanine,CuPc, Phthalocyanine blue, Pigment Blue 15;Phthalocyanine Copper(II);CuPC , Copper phthalocyanine
• CAS NO: 147-14-8
• Molecular Formula: C₃₂H₁₆N₈*Cu
• Molecular Weight: 576.07
• EINECS: 205-685-1
• Product Categories: oled materials;Dyes and Pigments;INORGANIC & ORGANIC CHEMICALS;Organometallics;electronic;Classes of Metal Compounds;Cu (Copper) Compounds;Functional Materials;Phthalocyanines;Phthalonitriles & Naphthalonitriles;Transition Metal Compounds;Electroluminescence;Blue needle crystal
• Mol File: 147-14-8.mol
• Article Data: 58

Chemical Properties

• Melting Point: 600°C (dec.)
• Appearance: Dark blue/Fine Crystalline Powder
• Density: 1.62[at 20℃]
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: <0.1 g/100 mL at 20℃
• Merck: 14,2520
• BRN: 4121848
• CAS DataBase Reference: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper(CAS DataBase Reference)
• NIST Chemistry Reference: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper(147-14-8)
• EPA Substance Registry System: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper(147-14-8)

Safety Data

• Safety Statements: 22-24/25
• RTECS: GL8510000
• TSCA: Yes
• Hazardous Substances Data: 147-14-8(Hazardous Substances Data)

Usage

Description

Copper(II) phthalocyanine, known as CuPc, has been used as an electron donor?with fullerene-C60 or phenyl-C61-butyric acid methyl ester (PCBM) in vacuum-deposited organic photovoltaics (OPV).?Power conversion efficiency of about 1% has been achieved [2] and improved efficiency of 4% with pentacene-doped CuPc layer . CuPc has also been used as a hole-injection material for light-emitting diodes. It has been reported that a thin CuPc layer may effectively enhance the hole injection from the anode to the emissive-polymer layer, resulting in a dramatic decrease of operating voltage of the device . Device stability was achieved by?depositing a copper phthalocyanine CuPc hole-injection layer?HIL on the ITO anode.

Chemical Properties

dark blue fine crystalline powder

Uses

Copper(II) phthalocyanine are involved in the study of photosensitizer chemistry for uniform polymerization, luminescence chemistry and spectrophotometric analysis, organic synthesis and polymerization. This pigment is used in enamels, linoleum, inks, plastics, and rubber goods. Photoisomerizable phthalocyanines are used in rewritable CD or DVD printing.Other applications in organic solar cells, biosensitizers and display devices such as OLED , OTFT, Wearable Display, and e-paper.

Application

Copper(II) phthalocyanine, known as CuPc, has been used as an electron donor with fullerene-C60 or phenyl-C61-butyric acid methyl ester (PCBM) in vacuum-deposited organic photovoltaics (OPV). Power conversion efficiency of about 1% has been achieved [2] and improved efficiency of 4% with pentacene-doped CuPc layer.CuPc has also been used as a hole-injection material for light-emitting diodes. It has been reported that a thin CuPc layer may effectively enhance the hole injection from the anode to the emissive-polymer layer, resulting in a dramatic decrease of operating voltage of the device. Device stability was achieved by depositing a copper phthalocyanine CuPc hole-injection layer HIL on the ITO anode. The improved stability could be contributed to the good match of its highest-occupied molecular orbital (HOMO) level to the work function of ITO, and the improved wetting property of organic materials on ITO. Moreover, CuPc has very weak absorption of light, with wavelengths from 400 to 500 nm, making it suitable for use in blue and green OLEDs.Effective electron-blocking was also observed for inorganic–organic hybrid perovskite solar cells when CuPc-doped spiro-OMeTAD was used as the hole-transporting layer.

General Description

Copper(II) phthalocynaine (CuPc) is a metal phthalocyanine dye that acts as a p-type semiconductor. It has a charge mobility of 10-4 cm2/Vs. It forms a chemically stable thin film that exhibits photoconductivity and catalytic activity.

Flammability and Explosibility

Notclassified

Purification Methods

Precipitate it twice from conc H2SO4 by slow dilution with water. It has also been purified by two or three sublimations at 580o in an argon flow at 300-400Pa. [Beilstein 26 III/IV 4256.]

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE BLUE POWDER SHADE REDDISH HEAT RESISTANCE 300 °C min LIGHT FASTNESS 7-8 ACID RESISTANCE 5 ALKALI RESISTANCE 5 FASTNESS TO BLEEDING 5 OIL ABSORPTION 40-45% SPECIFIC SURFACE 29 m 2 /g DENSITY 1.60 g/cm 3 RESIDUE ON 80 MESH 5.0% max WATER SOLUBLE 1.0% max VOLATITE 105 °C 1.0% max TINTING STRENGTH 100-105 %

TEST ITEMS

SPECIFICATION

APPEARANCE

BLUE POWDER

SHADE

REDDISH

HEAT RESISTANCE

300 °C min

LIGHT FASTNESS

7-8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

OIL ABSORPTION

40-45%

SPECIFIC SURFACE

29 m 2 /g

DENSITY

1.60 g/cm 3

RESIDUE ON 80 MESH

5.0% max

WATER SOLUBLE

1.0% max

VOLATITE 105 °C

1.0% max

TINTING STRENGTH

100-105 %

InChI:InChI=1/C32H16N8.Cu/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25;/h1-16H;/q-2;

Synthetic route

phthalonitrile (91-15-6) → copper phthalocyanine (147-14-8)

Conditions	Yield
With CuCl2*2H2O for 0.166667h; microwave irradiation;	98%
With CuCl2*2H2O at 190 - 210℃; for 0.25h; microwave irradiation;	88%
With copper diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 140℃; for 0.0833333h;	76%
With 1,1,1,3,3,3-hexamethyl-disilazane; copper(ll) bromide In N,N-dimethyl-formamide at 100℃; for 10h;	74%

phthalic anhydride (85-44-9) → copper phthalocyanine (147-14-8)

Conditions	Yield
With ammonium molybdate tetrahydrate; urea for 0.0833333h; microwave irradiation;	93%
With ammonium molybdate; urea at 200℃; for 0.166667h; microwave irradiation;	80%
Stage #1: phthalic anhydride With N,N-dimethyl-formamide; 1,1,1,3,3,3-hexamethyl-disilazane; copper dichloride; toluene-4-sulfonic acid at 150℃; for 10h; Stage #2: With sulfuric acid	62%

phthalimide (136918-14-4) → copper phthalocyanine (147-14-8)

Conditions	Yield
Stage #1: phthalimide With toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; copper(ll) bromide; N,N-dimethyl-formamide at 150℃; for 10h; Stage #2: With sulfuric acid	72%

copper phthalocyanine (147-14-8) → copper ftalocyanine tetra-3-sulfonyl chloride

Conditions	Yield
With chlorosulfonic acid; thionyl chloride 1.) 138 - 140 deg C, 3 h, 2.) 80 - 85 deg C, 3 h; Multistep reaction;

Upstream product

• 85-44-9 phthalic anhydride 
• 7789-45-9 copper(ll) bromide 
• 25248-76-4 29H,31H-phthalocyanine 
• 136918-14-4 phthalimide 
• 57-13-6 urea 
• 12775-96-1 copper 
• 91-15-6 phthalonitrile 
• 7787-70-4 copper(I) bromide 
• 184303-72-8 phthalanhydride 
• 160956-25-2 isoindole-1,3-diylidenediamine 
• 6046-93-1 copper(II) acetate monohydrate 
• 574-93-6 29H,31H-Phthalocyanine 
• 34946-82-2 copper(II) bis(trifluoromethanesulfonate) 
• 1835-65-0 Tetrafluorophthalonitrile 

Downstream Products

• 14832-14-5 C32Cl16CuN8, β 
• 28802-09-7 copper(II) phthalocyaninetetrasulfonyl chloride 
• 81869-68-3 Cu(C₈H₃N₂SO₂NH(C₆H₁₁))4 
• 74-90-8 hydrogen cyanide 
• 574-93-6 29H,31H-phthalocyanine 

Relevant articles and documents

Facile one-pot preparation of thermally and photochemically convertible soluble precursors of copper phthalocyanine and naphthalocyanine

Soluble copper phthalocyanine (CuPc) and naphthalocyanine (CuNc) precursors which can be converted thermally and photochemically into insoluble CuPc and CuNc, respectively, have been synthesized by a one-step reaction using commercially available chemicals. The Royal Society of Chemistry 2011.

(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

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.

Magneto-modified catalyst on the base of nanocrystalline CuO

The weakly oxidized nanocrystalline copper powders of different sizes (average particle size of 30 and 100nm) were used as the reactants at copper phthalocyanine (PcCu) formation. The nanocrystalline cupric oxide located at the particles surface serves as a heterogeneous magneto-controlled catalyst. A new effect of acceleration of chemical reaction rate controlled by low external steady magnetic field (～2 kOe) at room temperature was revealed and investigated on an example of formation of a coordination compound of PcCu. The rate of PcCu formation accelerated by 7-8 times after applying of a magnetic field.

Synthesis and characterization of copper phthalocyanine and tetracarboxamide copper phthalocyanine deposited mica-titania pigments

Combination pigments were synthesized by the deposition of copper phthalocyanine and tetracarboxamide copper phthalocyanine on a mica-titania pigment in dimethyl formamide solvent to improve color properties. The FT-IR and XRD analyses were performed to observe the crystal transformations of the pigments on the substrate. The stable beta form of copper phthalocyanine normally preferred in paint applications was obtained at 90 °C and 120°C, while tetracarboxamide copper phthalocyanine remained amorphous at all temperatures experimented. Pigment surface morphologies were investigated by SEM analysis. Copper phthalocyanine crystalline rods were observed on the mica-titania substrate, however, the tetracarboxamide copper phthalocyanine pigment did not exhibit any such crystalline structure due to its amorphous structure, which was confirmed by XRD analysis. Furthermore, nitrogen elemental analysis was performed to determine the amount of copper phthalocyanines adsorbed to the mica-titania surfaces at different temperatures. The resulting combination pigments showed enhanced luster, good dispersion, hue, and high color intensity.

Facile, liquid phase preparation of copper phthalocyanine microcrystals by means of thermal conversion of the dimethoxy-substituted solvent soluble phthalocyanine precursors

A simple procedure for the preparation of microcrystals of insoluble copper phthalocyanine (CuPc) by thermolysis of a dimethoxy-substituted precursor has been developed. Although the morphologies of the resultant microcrystals are practically independent from initial solution concentrations higher than ca. 0.03 mM of the dimethoxy-precursor, crystals with increased width are obtained with increasing the initial concentration of the precursor.

Improvement in the synthesis of metallophthalocyanines using microwave irradiation

A successful application of microwave irradiation, in which phthalocyanines were synthesized under solventless conditions from 1,2-phthalonitrile or phthalic anhydride and urea in the presence of metal templates is described. It was found that in comparison with conventional heating, the microwave process is a very useful alternative for cyclotetramerization processes because of reduction of the reaction time, better yield, and easy-to-perform procedure. Graphical Abstract.

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Effects of MN4-Type Coordination Structure in Metallophthalocyanine for Bio-Inspired Oxidative Desulfurization Performance

Oxidative desulfurization (ODS) is the promising new method for super deep desulfurization of fuel oil. The oxidative desulfurization performance of the metal-N4-chelates metallophthalocyanines (MPcs) is related to the chemical properties of conjugate structures and the central metal ions. Herein, a biomimetic catalytic system composed of metallophthalocyanines (MPcR4, M = Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II); R = -H, -COOH, -NO2, -NH2) and molecular O2 was performed to study the influence of MN4-type coordination structure in metallophthalocyanines for the degradation of dibenzothiophene (DBT) in model oil containing n-octane. The results reveal that the conjugate structures and the center metal ions of metallophthalocyanines played key roles in oxidative desulfurization performance. The inductive effect of different R substituents strongly affected the electron cloud distribution of the conjugate structures and the catalytic performance. Moreover, the catalytic activity of MPcs, which is related to the d electronic configuration and ligand-field effects, does not sequentially increase with the increase in the d electron number of central metal ions.

Nanostructural catalyst: Metallophthalocyanine and carbon nano-onion with enhanced visible-light photocatalytic activity towards organic pollutants

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.

Method for synthesizing metal phthalocyanine from phthalonitrile under catalysis of urea-choline chloride

The invention provides a clean method for synthesizing metal phthalocyanine from phthalonitrile or a phthalonitrile derivative substituted by different functional groups and a metal chloride or nitrate under catalysis of a urea-choline chloride eutecticevaporate green solvent. Multiple functional metal phthalocyanine compounds such as cobalt, copper, zinc, nickel, iron and manganese are synthesized under a gentle condition, the yield is high, and in addition, toxic and organic solvents such as amyl alcohol and expensive DBU (diazabicyclo) organic alkali catalysts which are used in a conventional process are not used. The urea-choline chloride eutecticevaporate solvent DES is adopted as a solvent for dissolving and dispersing reactants, meanwhile, a function of catalyzing formation of a phthalocyanine cycle is also achieved, and the reaction temperature for forming the phthalocyanine cycle is 110-130 DEG C. The low reaction temperature also ensures the uniformity, completeness and highpurity of a phthalocyanine product structure. The synthesis process is green, remarkable environment benefits can be made, the energy can be saved, and meanwhile, environment protection can be achieved.