26201-32-1

Basic information

• Product Name: Titanyl phthalocyanine
• Synonyms: Phthalocyanine titanium oxide §Oxytitanium phthalocyanine;TITANYL PHTHALOCYANINE, BETA MODIFICATI&;PhthalocyanineTitanyl;PHTHALOCYANINE TITANIUM OXIDE COMPLEX, Y-MODIFICATION;Oxytitamiumphthalocyanine;oxo[29H,31H-phthalocyaninato-N29, N30, N31, N32]-, (SP-5-12)-Titanium;29H,31H-Phthalocyanine titanium oxide
• CAS NO: 26201-32-1
• Molecular Formula: C₃₂H₁₆N₈OTi
• Molecular Weight: 576.39
• EINECS: 419-970-5
• Product Categories: Organometallics;electronic;pharmacetical;Infrared (IR) DyesPhotonic and Optical Materials;Organic Electronics and Photonics;Photonic and Optical Materials;Phthalocyanine and Porphyrin Dyes;Phthalocyanines;Hole Transporting MaterialsOrganic Electronics and Photonics;OLED and PLED Materials;oled materials
• Mol File: 26201-32-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 395.1 °C (dec.)(lit.)
• Appearance: /
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chlorobenzene [7]
• CAS DataBase Reference: Titanyl phthalocyanine(CAS DataBase Reference)
• NIST Chemistry Reference: Titanyl phthalocyanine(26201-32-1)
• EPA Substance Registry System: Titanyl phthalocyanine(26201-32-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 26201-32-1(Hazardous Substances Data)

Usage

Applications

Titanyl phthalocyanine (TiOPc), the family member of highly photosensitive phthalocyanine compounds, is one of the most successful leading materials used in the photocopying industry. Among various phthalocyanine semiconductors, oxotitanium phthalocyanine in the crystal form of phase-Y (Y-TiOPc) has attracted particular attention due to its high photosensitivity to NIR light. The quantum efficiency of Y-form TiOPc for photo carrier generation is reported to be almost 100% in high electric fields. Titanyl phthalocyanine is used as a water photo-oxidation agent and is built into sensors for NO2 detection. It has also been made into devices for of organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs) with photon to current efficiency (PCE) over 4% reported by using TiOPc as the light-harvesting dye and C60 as the electron acceptor.

Description

Titanyl phthalocyanine (TiOPc), the family member of highly photosensitive phthalocyanine compounds, is one of the most successful leading materials used in the photocopying industry. Among various phthalocyanine semiconductors, oxotitanium phthalocyanine in the crystal form of phase-Y (Y-TiOPc) has attracted particular attention due to its high photosensitivity to NIR light.?The quantum efficiency of Y-form TiOPc for photo carrier generation is reported to be almost 100% in high electric fields[2].

Chemical Properties

Blue to deep purple powder

Uses

Sensitizer for electrophotography.

General Description

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InChI:InChI=1/C32H16N8.O.Ti/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;;+2/rC32H16N8.OTi/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;1-2/h1-16H;/q-2;+2

Synthetic route

dichloro(phthalocyaninato)titanium(IV) (1208497-30-6, 16903-42-7) + water (7732-18-5) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
In pyridine Ti-complex was boiled in aq. pyridine for 2 h, cooled; filtered, washed with water, dried in vacuo at 100°C; elem. anal.;	97%
With hydrogenchloride In DMF (N,N-dimethyl-formamide); water at 100 - 120℃; for 1h;

titanium tetrachloride (7550-45-0) + phthalonitrile (91-15-6) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
In quinoline at 180℃; for 6h; Product distribution / selectivity;	76.8%
With thiourea In further solvent(s) TiCl4 was mixed with heptanol, heated to boiling, ligand was added, withor without thiourea, heated to 170°C, kept for 6 h; cooled, filtered, washed with toluene and MeOH, extd. with MeOH in Soxhlet for 4 h, dried in air; elem. anal.;	60%
In ethanol at -20.01℃; under 46504.7 Torr; for 1h;	60%

isoindole-1,3-diylidenediamine (160956-25-2, 160956-26-3, 160956-27-4, 160956-28-5, 160956-29-6) + titanium tetra-n-propoxide (3087-37-4) + phthalonitrile (91-15-6) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 198℃; for 2h; Product distribution / selectivity; Heating / reflux;	76%

tetrabutoxytitanium + isoindole-1,3-diylidenediamine (160956-25-2, 160956-26-3, 160956-27-4, 160956-28-5, 160956-29-6) → oxotitanium(IV) phthalocyanine (26201-32-1) + butan-1-ol (71-36-3)

Conditions	Yield
In 1-chloronaphthalene (CINp) at 140 - 200℃; for 2h; Product distribution / selectivity;	A 72% B n/a

→ oxotitanium(IV) phthalocyanine

Conditions	Yield
In 1-Chloronaphthalene at 195℃; for 3h; Product distribution / selectivity; Heating / reflux;	70%
In 1-methyl-pyrrolidin-2-one at 50 - 95℃; for 6h; Product distribution / selectivity;	1.5%
In 1-methyl-pyrrolidin-2-one at 24 - 100℃; Product distribution / selectivity; Electrochemical reaction;
In ethylene glycol at 24 - 100℃; Product distribution / selectivity; Electrochemical reaction;
In sulfolane Inert atmosphere;

dichlorotitanium phthalocyanine (1208497-30-6, 16903-42-7) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
With hydrogenchloride; N,N-dimethyl-formamide In water at 100 - 120℃; for 1h; pH=>= 6;

tetrabutoxytitanium + phthalonitrile (91-15-6) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
With pentan-1-ol; benzamide In xylene at 144℃; for 6h; Heating / reflux;

oxygen (80937-33-3) + titanium tetrachloride (7550-45-0) + phthalonitrile (91-15-6) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
In 1-Chloronaphthalene at 25 - 210℃; for 5h;
In Diphenylmethane; 1,1,2,2-tetrachloroethane at 40 - 210℃; for 6 - 8h; Product distribution / selectivity;

urea (57-13-6) + phthalonitrile (91-15-6) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
With tetrabutoxytitanium In nonyl alcohol at 160 - 170℃; for 0.1 - 6h; Product distribution / selectivity; Microwave and ultrasonic energy;

isoindole-1,3-diylidenediamine (160956-25-2, 160956-26-3, 160956-27-4, 160956-28-5, 160956-29-6) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
With quinoline; tetrabutoxytitanium at 170 - 180℃; for 0.1 - 6h; Product distribution / selectivity;

tetrabutoxytitanium + 4,5-dichlorophthalonitrile (139152-08-2) + phthalonitrile (91-15-6) → oxotitanium(IV) phthalocyanine (26201-32-1) + C32H14Cl2N8OTi

Conditions	Yield
With benzamide In pentan-1-ol; xylene Reflux;

tetrabutoxytitanium + urea (57-13-6) + phthalonitrile (91-15-6) → oxotitanium(IV) phthalocyanine (26201-32-1)

Conditions	Yield
With tin(IV) chloride In octanol at 155 - 159℃; for 6h; Inert atmosphere;	22.77 g

oxotitanium(IV) phthalocyanine (26201-32-1) + 2,6-diisopropylphenyl isocyanate (28178-42-9) → (2,6-diisopropylphenylimido)phthalocyaninatotitanium(IV) (1276014-86-8)

Conditions	Yield
In further solvent(s) byproducts: CO2; under N2; mixt. of Ti complex and ((CH3)2CH)2C6H3NCO (20-fold excess) inchloronaphthalene heated at 180°C for 6 h, released CO2 replaced by N2 from time to time; mixt. cooled, pptn. by addn. of hexane, solid filtered off, extd. repeatedly with MeCN and toluene (10x50 mL each) under reflux, washed with pentane, dried at 120°C under vac. for 3 h; elem. anal.;	83%

oxotitanium(IV) phthalocyanine (26201-32-1) + p-Tolylisocyanate (622-58-2) → (N,N'-di(p-tolyl)ureato-κ2N,N')phthalocyaninatotitanium(IV) (1217488-65-7)

Conditions	Yield
In further solvent(s) byproducts: CO2; under N2; mixt. of Ti complex and p-tolyl isocyanate in chloronaphthalene heated at 180°C for 6 h, released CO2 replaced by N2 from time to time; soln. cooled, pptn. by addn. of hexane, solid filtered off, extd. with rMeCN and toluene (10x50 mL each) under reflux, washed with pentane, dried at 120°C under vac. for 3 h; elem. anal.;	76%
In further solvent(s) according to Darwish, W. et al., Acta Cryst. E61 2005, m1280-1282; Darwish, W., Dissertation, Philipps University, Marburg, Germany, 2006; solvent: chloronaphthalene;

oxotitanium(IV) phthalocyanine (26201-32-1) + tetrapentylammonium bromide (866-97-7)

Conditions	Yield
With fluorenone radical anion sodium contact ion pair In 1,2-dichloro-benzene at 80℃; for 24h;	74%

Conditions	Yield
In further solvent(s) byproducts: CO2; under N2; mixt. of Ti complex and mesityl isocyanate in chloronaphthalene heated at 180°C for 6 h, released CO2 replaced by N2 from time to time; soln. cooled, pptn. by addn. of hexane, solid filtered off, extd. with rMeCN and toluene (10x50 mL each) under reflux, washed with pentane, dried at 120°C under vac. for 3 h; elem. anal.;	73%

oxotitanium(IV) phthalocyanine (26201-32-1) + tetrahexylammonium bromide (4328-13-6) + 1,2-dichloro-benzene (95-50-1) → C32H16N8OTi(1-)*C24H52N(1+)*C6H4Cl2

Conditions	Yield
With fluorenone radical anion sodium contact ion pair at 80℃; for 24h;	66%

oxotitanium(IV) phthalocyanine (26201-32-1) + triptycene (477-75-8) + tetramethylphosphonium bromide (4519-28-2) + 1,2-dichloro-benzene (95-50-1)

Conditions	Yield
Stage #1: oxotitanium(IV) phthalocyanine; tetramethylphosphonium bromide; 1,2-dichloro-benzene With fluorenone radical anion sodium contact ion pair at 100℃; for 2h; Glovebox; Inert atmosphere; Stage #2: triptycene In benzonitrile at 20 - 100℃; for 3h;	65%

→ sulfido(phthalocyaninato)titanium(IV)

Conditions

Yield

With triphenylphosphine In further solvent(s) (N2); Schlenk techniques; phthalocyanine deriv. and P4S10 heated in chloronaphthalene at 160°C for 10 h; pptd. by addn. of hexane; washedby extn. with refluxing MeCN, toluene; washed with pentane; dried at 12 0.degre.C for 1 h under 1E-3 mbar; heated with triphenylphosphine to a melt at 160°C for 4 h; washedwith refluxing MeCN, toluene; washed with ether; dried at 120.degre.C f or 1 h under 1E-3 mbar;

57%

oxotitanium(IV) phthalocyanine (26201-32-1) + 4-aza-1-methylazoniabicyclo<2.2.2>octane iodide (14968-74-2) → C32H16N8OTi(1-)*C7H15N2(1+)*C20H14

Conditions	Yield
With fluorenone radical anion sodium contact ion pair In 1,2-dichloro-benzene at 100℃; for 24h;	43%

oxotitanium(IV) phthalocyanine (26201-32-1) + 4-aza-1-methylazoniabicyclo<2.2.2>octane iodide (14968-74-2)

Conditions	Yield
With fluorenone radical anion sodium contact ion pair In 1,2-dichloro-benzene at 100℃; for 24h;	38%

+ 4-aza-1-methylazoniabicyclo<2.2.2>octane iodide (14968-74-2) → C32H16N8OTi(1-)*C7H15N2(1+)*C20H14

Conditions	Yield
Stage #1: oxotitanium(IV) phthalocyanine; N-methyl-1,4-diazabicyclo<2.2.2>octanium iodide With fluorenone radical anion sodium contact ion pair In 1,2-dichloro-benzene at 100℃; for 24h; Stage #2: triptycene In benzonitrile; 1,2-dichloro-benzene at 20℃; for 4h;	27%

oxotitanium(IV) phthalocyanine (26201-32-1) + haematoxylin (1621-46-1, 17647-60-8, 98092-70-7, 517-28-2) → ((C32H16N8)Ti)2C16H9O(OH)(O)4

Conditions	Yield
In further solvent(s) Ti-complex was dissolved in 1-chloronaphthalene at 180°C under N2, hematoxylin was added, the soln. was stirred for 15 min; filtd., hexane was added to induce pptn., ppt. was collected and recrystd. from 1-chloronaphthalene/MeOH;	19.1%

oxotitanium(IV) phthalocyanine (26201-32-1) + gallium phthalocyanine hydroxide (63371-84-6) + μ-oxogallium phthalocyanine → PcGa-O-TiPc

Conditions	Yield
With hydrogenchloride; N,N-dimethyl-formamide In water at 100 - 120℃; for 1h; pH=>= 6;

Upstream product

• 160956-25-2 isoindole-1,3-diylidenediamine 
• 5593-70-4 titanium (IV) butoxide 
• 57-13-6 urea 
• 91-15-6 phthalonitrile 
• 60-35-5 acetamide 
• 7664-41-7 ammonia 
• 55-21-0 benzamide 
• 3087-37-4 titanium tetra-n-propoxide 
• 80937-33-3 oxygen 
• 7550-45-0 titanium tetrachloride 
• 1208497-30-6 titanium(IV) chloride phthalocyaninate 
• 139152-08-2 4,5-dichlorophthalonitrile 
• 1208497-30-6 dichlorotitanium phthalocyanine 
• 7732-18-5 water 

Downstream Products

• 1276014-89-1 (N,N'-dimesitylureato-κ2N,N')phthalocyaninatotitanium(IV) 
• 1217488-65-7 (N,N'-di(p-tolyl)ureato-κ2N,N')phthalocyaninatotitanium(IV) 
• 1276014-86-8 (2,6-diisopropylphenylimido)phthalocyaninatotitanium(IV) 

Relevant articles and documents

The metal phthalocyanine compound crystal and its manufacturing method, using the electrophotographic photosensitive member, method, Image forming device, and Image forming apparatus and process cartridge for

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An N-phenyl-diphenylisoindole derivative having the following formula (1): wherein each of R1 and R2 represents a hydrogen atom, a substituted or an unsubstituted alkyl group, a substituted or an unsubstituted alkoxy group, a substituted or an unsubstituted phenyl group, or a substituted or an unsubstituted phenoxy group; R3 represents a hydrogen atom, a substituted or an unsubstituted alkyl group, a substituted or an unsubstituted alkoxy group, a substituted or an unsubstituted phenyl group, a substituted or an unsubstituted phenoxy group, or has the following formula (2): wherein each of R4 and R5 represents a substituted or an unsubstituted alkyl group, or a substituted or an unsubstituted phenyl group; 1 represents an integer of from 1 to 4; and each of m and n represents an integer of from 1 to 5.

TITANYL PHTHALOCYANINE PROCESSES AND PHOTOCONDUCTORS THEREOF

A process which includes treating, mixing, or contacting a Type I titanyl phthalocyanine with a weak acid with a pKa of at least equal to or greater than about 0; dissolving the acid treated Type I titanyl phthalocyanine in a solution of a trihaloacetic acid and an alkylene halide; adding the formed mixture to a solution of an alcohol and an alkylene halide thereby precipitating a Type Y titanyl phthalocyanine; and treating the Type Y titanyl phthalocyanine with monohalobenzene thereby resulting in a high sensitivity titanyl phthalocyanine.