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574-93-6

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574-93-6 Usage

Description

Phthalocyanine is a macrocyclic compound, It consists of four isoindole-class [(C6H4)C2N] units linked by four nitrogen atoms to form a conjugated chain, which take play in hosting various different metal ions in its centre. This macrocyclic structure like porphyrins(biopigments) is highly coloured Phthalocyanine derivatives derived from the basic compound of (C6H4C2N)4N4 are used as light-fast blue or green pigments. The hosted metals and substituted groups result in distinct colors; phthalocyanine (blue-green), copper phthalocyanine (blue), chlorinated copper phthalocyanine (green), and sulfonated copper phthalocyanine (green). They have also been involved in the study of photosensitizer chemistry or metal complex chemistry such as transition-metal complex catalyst chemistry for uniform polymerization, luminescence chemistry and spectrophotometric analysis, organic synthesis and polymerization. Phthalocyanine pigments are used in enamels, linoleum, inks, plastics, and rubber goods. Photoisomerizable phthalocyanines are used in rewritable CD or DVD printing. Some phthalocyanines such as fluoraluminium phthalocyanine are used in cancer treatment. Due to pi-electron cloud overlaps, phthalocyanines exhibit semiconductor property. Organic semiconductors have some merits of self radiation, flexibility, light weight, easy fabrication, and low cost. They have been investigated as organic electroluminescence materials for the applications in organic solar cells, biosensitizers and display devices such as OLED(Organic Light Emitting Diode), OTFT(Organic Thin Film Transistor), Wearable Display, and e-paper.Phthalocyanine green is a bluish green pigment with outstanding lightfastness and stability commercially produced since 1938.Phthalocyanine blue is a bright blue pigment with outstanding properties which was in use by many modern painters such as Mondrian, Pollock, and others.

Organic pigment

Phthalein is an important organic pigment. Its chromatography is mainly blue and green. It is of bright color and strong coloring force. It features excellent weatherability, heat resistance, solvent resistance, acid resistance and alkali resistance. It is widely used in paints, ink, plastic coloring, pigment printing, synthetic fiber raw coloring etc.. It can also be used as catalyst, grease, electrophotographic sensitizer, solar cell and so on. Its main variety is copper phthalocyanine (phthalocyanine blue). Metal phthalocyanines are also used in a small amount. Copper phthalocyanine has a variety of crystal forms, usually taking the alpha and beta forms. The hydrogen atoms on the benzene ring are replaced by halogen, and the color changes from blue to green. Phthalein, also known as phthalocyanine, is a kind of dark compound. The structure is similar to porphyrin ring (or porphyrin complex, porphyrin). It is a dye consisting of four pyrrole nuclei with porphyrin ring structure. According to the molecular orbital theory, the conjugated system with this structure is very stable. Phthalocyanine is used as a blue to green pigment with the highest fastness. Afterwards, dyes with excellent properties are derived from various methods. It can be divided into metal phthalocyanine and non metal phthalocyanine. There are two types of metal phthalocyanines: the first type contains copper, iron, zinc, cobalt, platinum, etc. The radius of the atom is close to the radius of the center gap of the phthalocyanine molecule. These metals are bonded to two nitrogen atoms in four nitrogen atoms by atomic bonds, and the other two nitrogen atoms are bonded by valence bonds. The other type contains sodium, potassium, barium, cadmium, magnesium, lead and so on. The atomic radius of the metal atom is too long and cannot form the valence bond with phthalocyanine. It can only be combined with two nitrogen atoms by atomic chain into salt. The former is treated with concentrated sulfuric acid, and the metal is not removed. It is slightly soluble in organic solvents and can be sublimed under high temperature and vacuum. The latter, in the case of acid or water, is easy to remove. It is insoluble in organic solvents and does not sublimate under high temperature and vacuum. Four benzene rings in phthalocyanine molecules are more easily substituted and sulfonated. The dyes derived from phthalocyanines include direct dyes, sulphur dyes, vat dyes, phthalocyanine dye (phthalocyanines), special water-soluble dyes and reactive dyes. Metal phthalocyanines are prepared by co heating of phthalic anhydride or phthalonitrile with metal or metal salts.

Chemical Properties

Blue to purple powder

Uses

Phthalocyanine is a common macrocylic blue-green dye able to form coordination complexes with many elements on the periodic table.

Definition

Different sources of media describe the Definition of 574-93-6 differently. You can refer to the following data:
1. ChEBI: A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.
2. phthalocyanine: A synthetic compoundhaving molecules with fourisoindole rings linked by –N= bridges.The structure is similar to that of theporphyrins. It can form complexeswith central metal ions. Copperphthalocyanines are used as dyes.

Flammability and Explosibility

Notclassified

Agricultural Uses

Phthalocyanine is a group of benzoporphyrins which have strong pigmenting power, forming a family of dyes. The basic structure of the molecule comprises four isoindole groups (C6H4,)C2N, joined by four nitrogen atoms. Four commercially important modifications are: (a) metal free phthalocyanine (C6H4C2N)4, having a bluegreen color,(b copper phthalocyanine in which a copper atom is held by secondary valences of the isoindole nitrogen atoms, (c) chlorinated copper phthalocyanine, green, in which 15 to 16 hydrogen atoms are replaced by chlorine, and (d) sulphonated copper phthalocyanine, water-soluble and green, in which two hydrogens are replaced by sulphonic acid groups. It is used in decorative enamels and automotive finishes; chlorophyll and haems have basic phthalocyanine structures in their molecules.

Purification Methods

Purify phthalocyanine by sublimation (two to three times) in an argon flow at 300-400Pa; and similarly for the Cu(II), Ni(II), Pb(II), VO(II) and Zn(II) phthalocyanine complexes. [Beilstein 26 III/IV 4255.]

Check Digit Verification of cas no

The CAS Registry Mumber 574-93-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 4 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 574-93:
(5*5)+(4*7)+(3*4)+(2*9)+(1*3)=86
86 % 10 = 6
So 574-93-6 is a valid CAS Registry Number.
InChI:InChI=1/C32H18N8/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,(H2,33,34,35,36,37,38,39,40)

574-93-6 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (P0355)  Phthalocyanine  >93.0%(N)

  • 574-93-6

  • 25g

  • 995.00CNY

  • Detail
  • TCI America

  • (P1795)  Phthalocyanine (purified by sublimation)  >98.0%(N)

  • 574-93-6

  • 1g

  • 530.00CNY

  • Detail
  • Alfa Aesar

  • (32073)  Phthalocyanine   

  • 574-93-6

  • 1g

  • 209.0CNY

  • Detail
  • Alfa Aesar

  • (32073)  Phthalocyanine   

  • 574-93-6

  • 5g

  • 695.0CNY

  • Detail
  • Alfa Aesar

  • (32073)  Phthalocyanine   

  • 574-93-6

  • 25g

  • 1654.0CNY

  • Detail
  • Aldrich

  • (253103)  29H,31H-Phthalocyanine  β-form, 98%

  • 574-93-6

  • 253103-1G

  • 317.07CNY

  • Detail
  • Aldrich

  • (253103)  29H,31H-Phthalocyanine  β-form, 98%

  • 574-93-6

  • 253103-5G

  • 1,088.10CNY

  • Detail

574-93-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name phthalocyanine

1.2 Other means of identification

Product number -
Other names Phthalocyanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:574-93-6 SDS

574-93-6Synthetic route

phthalonitrile
91-15-6

phthalonitrile

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]-undecen-7-ene In ethylene glycol at 35 - 40℃; for 3h; Product distribution; Further Variations:; Temperatures; Solvents; Reagents; UV-irradiation;100%
With sodium methylate; blue zeolite In methanol at 40℃; for 72h;76%
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In N,N-dimethyl-formamide at 150℃; for 24h;72%
phthalimide
136918-14-4

phthalimide

ammonium molybdate

ammonium molybdate

1-chloro-3-isopropyl-2-methyl-benzene
127450-94-6

1-chloro-3-isopropyl-2-methyl-benzene

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With urea; copper(I) chloride97%
zinc phthalocyanine
14320-04-8

zinc phthalocyanine

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With pyridine hydrochloride In pyridine at 120℃; for 17h; Inert atmosphere;91%
3-Imino-5,6-bis-octyloxy-3H-isoindol-1-ylamine

3-Imino-5,6-bis-octyloxy-3H-isoindol-1-ylamine

subphthalocyanine

subphthalocyanine

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

2,3-bis(octyloxy)phthalocyanine

2,3-bis(octyloxy)phthalocyanine

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 80℃; for 12h;A n/a
B 90%
phthalimide
136918-14-4

phthalimide

ammonium molybdate

ammonium molybdate

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With urea; copper(I) chloride90%
isopropylamine
75-31-0

isopropylamine

phthalonitrile
91-15-6

phthalonitrile

A

1-isopropylamino-3-(isopropylimino)isoindole
104830-26-4

1-isopropylamino-3-(isopropylimino)isoindole

B

NdI3(iPrNH2)4

NdI3(iPrNH2)4

C

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With NdI3(THF)3 Inert atmosphere;A 85%
B n/a
C n/a
isopropylamine
75-31-0

isopropylamine

phthalonitrile
91-15-6

phthalonitrile

A

1-isopropylamino-3-(isopropylimino)isoindole
104830-26-4

1-isopropylamino-3-(isopropylimino)isoindole

B

GdI3(iPrNH2)4

GdI3(iPrNH2)4

C

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With GdI3(THF)3 at 20℃; for 8h; Inert atmosphere;A 78%
B n/a
C n/a
isopropylamine
75-31-0

isopropylamine

phthalonitrile
91-15-6

phthalonitrile

A

1-isopropylamino-3-(isopropylimino)isoindole
104830-26-4

1-isopropylamino-3-(isopropylimino)isoindole

B

DyI3(i-PrNH2)4

DyI3(i-PrNH2)4

C

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With dysprosium(III) iodide at 20℃; for 8h; Inert atmosphere;A 73%
B n/a
C n/a
tetrachlorosilane
10026-04-7, 53609-55-5

tetrachlorosilane

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
In quinoline; N,N-dimethyl-formamide73%
In quinoline; N,N-dimethyl-formamide70%
lithium phthalocyanine radical
103088-30-8

lithium phthalocyanine radical

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With hydroquinone at 150℃; under 0.01 Torr; for 2h; Product distribution; also in water at 20 deg C; other reagents, solvent;70%
zinc(II) phthalocyanine
14320-04-8

zinc(II) phthalocyanine

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With pyridine; pyridine hydrochloride for 17h; Inert atmosphere;65.7%
3,6-didecyloxyphthalonitrile
116453-83-9

3,6-didecyloxyphthalonitrile

phthalonitrile
91-15-6

phthalonitrile

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

1,4,1'',4''-tetrakis(decyloxy)phthalocyanine

1,4,1'',4''-tetrakis(decyloxy)phthalocyanine

Conditions
ConditionsYield
Stage #1: 3,6-didecyloxyphthalonitrile With lithium n-pentyloxide In pentan-1-ol for 2h; Heating;
Stage #2: phthalonitrile With lithium n-pentyloxide In pentan-1-ol for 4h; Heating;
A 62%
B 7%
boron subphthalocyanine chloride

boron subphthalocyanine chloride

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

monoaminophthalocyanine

monoaminophthalocyanine

Conditions
ConditionsYield
In various solvent(s) Heating;A n/a
B 60%
phthalimide
136918-14-4

phthalimide

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In N,N-dimethyl-formamide at 150℃; for 10h;58%
Stage #1: phthalimide With N,N-dimethyl-formamide; 1,1,1,3,3,3-hexamethyl-disilazane; magnesium bromide; toluene-4-sulfonic acid at 150℃; for 4h;
Stage #2: With sulfuric acid
34%
5-tert-butyl-1,3-diiminoisoindoline

5-tert-butyl-1,3-diiminoisoindoline

subphthalocyanine

subphthalocyanine

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

2-tert-butylphthalocyanine

2-tert-butylphthalocyanine

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 80℃; for 12h;A n/a
B 57%
methylamine
74-89-5

methylamine

phthalonitrile
91-15-6

phthalonitrile

A

NdI3(MeNH2)(1,3-bis(methylimino)isoindoline)

NdI3(MeNH2)(1,3-bis(methylimino)isoindoline)

B

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

C

1,3-bis(methylimino)isoindoline

1,3-bis(methylimino)isoindoline

Conditions
ConditionsYield
With neodymium(III) iodide at 10℃; for 6h; Inert atmosphere;A 0.48 g
B n/a
C 52%
phthalic anhydride
85-44-9

phthalic anhydride

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In N,N-dimethyl-formamide at 150℃; for 10h;42%
With ammonium molybdate; urea at 190 - 200℃; for 4h;
propylamine
107-10-8

propylamine

phthalonitrile
91-15-6

phthalonitrile

A

NdI3(nPrNH2)5

NdI3(nPrNH2)5

B

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

C

1,3-bis-n-propyliminoisoindoline
93423-55-3

1,3-bis-n-propyliminoisoindoline

Conditions
ConditionsYield
With neodymium(III) iodide at 20℃; for 8h; Inert atmosphere;A 1.077 g
B n/a
C 27%
C25H22N4O3S

C25H22N4O3S

1,8-diazabicyclo[5.4.0]undec-7-ene
6674-22-2

1,8-diazabicyclo[5.4.0]undec-7-ene

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
In pentan-1-ol Heating; Inert atmosphere;20%
phthalonitrile
91-15-6

phthalonitrile

2,3-bis-hexylthio-maleonitrile

2,3-bis-hexylthio-maleonitrile

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

22,23-di(hexylthio)-27H,29H-tribenzo[b,g,l]porphyrazine

22,23-di(hexylthio)-27H,29H-tribenzo[b,g,l]porphyrazine

Conditions
ConditionsYield
With iodine; magnesium In butan-1-ol for 12h; Heating;A n/a
B 17%
1,2-dicyanobenzo-4,5-(15-crown-5)
110682-73-0

1,2-dicyanobenzo-4,5-(15-crown-5)

phthalonitrile
91-15-6

phthalonitrile

A

C40H32N8O5

C40H32N8O5

B

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With lithium In pentan-1-ol for 2h; Heating;A 16%
B n/a
2-aminopyridine
504-29-0

2-aminopyridine

phthalonitrile
91-15-6

phthalonitrile

A

1,3-bis-(2-pyridylimino)isoindoline
14526-01-3

1,3-bis-(2-pyridylimino)isoindoline

B

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With neodymium(III) iodide In benzene at 80℃; for 20h; Inert atmosphere;A 16%
B n/a
phthalonitrile
91-15-6

phthalonitrile

(Z)-1,2-bis(2-hydroxyethylthio)ethene-1,2-dicarbonitrile

(Z)-1,2-bis(2-hydroxyethylthio)ethene-1,2-dicarbonitrile

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

22,23-di(2-hydroxyethylthio)-μ-27H,29H-tribenzo[b,g,l]porphyrazine
675832-95-8

22,23-di(2-hydroxyethylthio)-μ-27H,29H-tribenzo[b,g,l]porphyrazine

Conditions
ConditionsYield
Stage #1: phthalonitrile; (Z)-1,2-bis(2-hydroxyethylthio)ethene-1,2-dicarbonitrile With iodine; magnesium In butan-1-ol for 12h; Heating;
Stage #2: With trifluoroacetic acid at 20℃; for 3h;
A n/a
B 12%
3-Imino-6-p-tolylsulfanyl-3H-isoindol-1-ylamine
183059-89-4

3-Imino-6-p-tolylsulfanyl-3H-isoindol-1-ylamine

subphthalocyanine

subphthalocyanine

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

2-(tolylthio)phthalocyanine

2-(tolylthio)phthalocyanine

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 80℃; for 12h;A n/a
B 11%
3-Imino-6-(toluene-4-sulfinyl)-3H-isoindol-1-ylamine
183059-90-7

3-Imino-6-(toluene-4-sulfinyl)-3H-isoindol-1-ylamine

subphthalocyanine

subphthalocyanine

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

2-(tolylsulfinyl)phthalocyanine

2-(tolylsulfinyl)phthalocyanine

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 80℃; for 12h;A n/a
B 10%
C24H12BN6(1+)*Cl(1-)

C24H12BN6(1+)*Cl(1-)

4,5-di-[5-(4-phenoxy)-10,15,20-triphenyl porphyrin]-1,2-dicarbonitrile zinc (II)

4,5-di-[5-(4-phenoxy)-10,15,20-triphenyl porphyrin]-1,2-dicarbonitrile zinc (II)

A

2,3-di-[5-(4-phenoxy)-10,15,20-triphenyl porphyrin zinc(II) ]phthalocyanine

2,3-di-[5-(4-phenoxy)-10,15,20-triphenyl porphyrin zinc(II) ]phthalocyanine

B

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 120℃; for 24h;A 6%
B n/a
C61H65N11O5
130326-42-0

C61H65N11O5

A

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

B

1-(2'-(9',16',23'-tris(1,1-dimethylethyl)phthalocyaninoxy))-2-ethyl-2-methyl-3-(2-phthalocyaninoxy)propane
130326-44-2

1-(2'-(9',16',23'-tris(1,1-dimethylethyl)phthalocyaninoxy))-2-ethyl-2-methyl-3-(2-phthalocyaninoxy)propane

Conditions
ConditionsYield
In various solvent(s) at 160℃; for 60h;A n/a
B 2%
In various solvent(s) at 160℃; for 60h; Yields of byproduct given;
cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

cobalt(II) phthalocyanine
3317-67-7

cobalt(II) phthalocyanine

Conditions
ConditionsYield
With butyl(2-hydroxyethyl)dimethylammonium acetate at 100℃; Ionic liquid; Inert atmosphere;99%
With tributyl-amine In pentan-1-ol at 160℃; for 2h; Inert atmosphere;20 mg
nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

nickel(II) phthalocyanine
14055-02-8

nickel(II) phthalocyanine

Conditions
ConditionsYield
With butyl(2-hydroxyethyl)dimethylammonium acetate at 100℃; Ionic liquid; Inert atmosphere;98%
lead acetate
301-04-2

lead acetate

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

lead(II) phthalocyanine
15187-16-3

lead(II) phthalocyanine

Conditions
ConditionsYield
With butyl(2-hydroxyethyl)dimethylammonium acetate at 100℃; Ionic liquid; Inert atmosphere;94%
zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

zinc(II) phthalocyanine
14320-04-8

zinc(II) phthalocyanine

Conditions
ConditionsYield
With butyl(2-hydroxyethyl)dimethylammonium acetate at 100℃; Ionic liquid; Inert atmosphere;92%
With tributyl-amine In pentan-1-ol at 160℃; for 2h; Inert atmosphere;26 mg
1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene
157131-39-0

1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene

[Ru2(η6-p-cymene)2(C6H2O4)Cl2]
1039768-31-4

[Ru2(η6-p-cymene)2(C6H2O4)Cl2]

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

[phthalocyanine*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-2,5-dioxido-1,4-benzoquinonato)3][trifluoromethanesulfonate]6

[phthalocyanine*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-2,5-dioxido-1,4-benzoquinonato)3][trifluoromethanesulfonate]6

Conditions
ConditionsYield
In methanol for 24h; Reflux;91%
iron(III) chloride

iron(III) chloride

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

phthalocyaninatoiron(III) chloride

phthalocyaninatoiron(III) chloride

Conditions
ConditionsYield
With butyl(2-hydroxyethyl)dimethylammonium acetate at 100℃; Ionic liquid; Inert atmosphere;90%
lanthanum(III) acetylacetonate hydrate

lanthanum(III) acetylacetonate hydrate

C98H78N8O2

C98H78N8O2

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

C130H90La2N16O2

C130H90La2N16O2

Conditions
ConditionsYield
Stage #1: lanthanum(III) acetylacetonate hydrate; C98H78N8O2 In octanol for 16h; Reflux; Inert atmosphere;
Stage #2: 29H,31H-Phthalocyanine In octanol for 18h; Reflux; Inert atmosphere;
86%
29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

lithium phthalocyanine radical
103088-30-8

lithium phthalocyanine radical

Conditions
ConditionsYield
With iodine In water; acetone at 20℃; for 12h;78%
1,2,4,5-tetrakis{2-(pyridin-4-yl)vinyl}benzene

1,2,4,5-tetrakis{2-(pyridin-4-yl)vinyl}benzene

(η6-p-cymRu)2(μ4-5,8-dihydroxy-1,4-naphthoquinone)Cl2

(η6-p-cymRu)2(μ4-5,8-dihydroxy-1,4-naphthoquinone)Cl2

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

[phthalocyanine*Ru8(p-cymene)8(1,2,4,5-tetrakis{2-(pyridin-4-yl)vinyl}benzene)2(μ-5,8-dioxido-1,4-naphthoquinonato)4][trifluoromethanesulfonate]8

[phthalocyanine*Ru8(p-cymene)8(1,2,4,5-tetrakis{2-(pyridin-4-yl)vinyl}benzene)2(μ-5,8-dioxido-1,4-naphthoquinonato)4][trifluoromethanesulfonate]8

Conditions
ConditionsYield
In methanol for 24h; Reflux;76%
dysprosium(III) chloride

dysprosium(III) chloride

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

C68H44Cl2Dy2N16O2S2

C68H44Cl2Dy2N16O2S2

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at 189℃; for 0.166667h; Inert atmosphere;68.2%
29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

POTBC

POTBC

Conditions
ConditionsYield
With pyridine; phosphorus tribromide at 100℃; for 6h;67%
bis(pentamethylcyclopentadienyl)cobalt(II)
74507-62-3

bis(pentamethylcyclopentadienyl)cobalt(II)

hexane
110-54-3

hexane

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

benzonitrile
100-47-0

benzonitrile

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

(Cp*2Co+)(H2Pc•-)·0.5C6H4Cl2·0.7C6H5CN·0.3C6H14

(Cp*2Co+)(H2Pc•-)·0.5C6H4Cl2·0.7C6H5CN·0.3C6H14

Conditions
ConditionsYield
Stage #1: bis(pentamethylcyclopentadienyl)cobalt(II); 29H,31H-Phthalocyanine; 1,2-dichloro-benzene at 100℃; for 4h;
Stage #2: benzonitrile at 100℃; for 2h;
Stage #3: hexane for 1461h;
64%
tetrahydrofuran
109-99-9

tetrahydrofuran

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

29H,31H-Phthalocyanine
574-93-6

29H,31H-Phthalocyanine

uranium(IV) chloride
10026-10-5

uranium(IV) chloride

C48H48Cl3LiN8O4U

C48H48Cl3LiN8O4U

Conditions
ConditionsYield
In Triethylene glycol dimethyl ether at 189℃; for 0.0833333h; Inert atmosphere;59%

574-93-6Relevant articles and documents

Metal-free phthalocyanine single crystal: Solvothermal synthesis and near-infrared electroluminescence

Bai, Qing-Long,Zhang, Chun-Hua,Song, Juan-Juan,Liu, Jing-Hai,Feng, Yan-Chun,Duan, Li-Mei,Cheng, Chuan-Hui

, p. 764 - 768 (2016)

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.

-

Barrett,Linstead,Tuey

, p. 1809,1814, 1815, 1816, 1820 (1939)

-

Synthesis of Novel Unsymmetrical Monoaminated Phthalocyanines

Sastre, Angela,Torres, Tomas,Hanack, Michael

, p. 8501 - 8504 (1995)

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.

An efficient two-step synthesis of metal-free phthalocyanines using a Zn(ii) template

Alzeer, Jawad,Roth, Phillipe J. C.,Luedtke, Nathan W.

, p. 1970 - 1971 (2009)

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

Synthesis of metal-free phthalocyanines in functionalized ammonium ionic liquids

Chauhan,Agarwal, Shweta,Kumari, Pratibha

, p. 2917 - 2925 (2007)

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.

Mutual influence of ligands and reactivity of Gd and Dy acidophthalocyaninate complexes

Lomova,Andrianova

, p. 660 - 664 (2004)

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

Cerium-promoted formation of metal-free phthalocyanines

Lee, Chi-Hang,Ng, Dennis K.P

, p. 4211 - 4214 (2002)

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.

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

Brzezinski, Krzysztof,Butsyk, Olena,Chaur, Manuel N.,Czyrko-Horczak, Justyna,Echegoyen, Luis,Olejnik, Piotr,Plonska-Brzezinska, Marta E.,Regulska, Elzbieta,Tomczykowa, Monika,Zubyk, Halyna

, p. 10910 - 10920 (2020/03/30)

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.

DNA interaction and anticancer properties of new peripheral phthalocyanines carrying tosylated 4-morpholinoaniline units

?mero?lu, ?pek,?zel, Arzu,ünver, Yasemin,Barut, Burak,Durmu?, Mahmut,Ertem, Beytullah,Kantekin, Halit,Yal??n, Can ?zgür,Yalazan, Halise

, (2020/01/02)

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.

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