81-32-3

Basic information

• Product Name: perylene-3,4,9,10-tetracarboxylic acid
• Synonyms: perylene-3,4,9,10-tetracarboxylic acid
• CAS NO: 81-32-3
• Molecular Formula: C24H12O8
• Molecular Weight: 428.34728
• EINECS: 201-343-0
• Mol File: 81-32-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 912.4 °C at 760 mmHg
• Flash Point: 519.4 °C
• Appearance: /
• Density: 1.739 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.939
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.17±0.30(Predicted)
• CAS DataBase Reference: perylene-3,4,9,10-tetracarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: perylene-3,4,9,10-tetracarboxylic acid(81-32-3)
• EPA Substance Registry System: perylene-3,4,9,10-tetracarboxylic acid(81-32-3)

Safety Data

• Hazardous Substances Data: 81-32-3(Hazardous Substances Data)

Usage

General Description

Perylene-3,4,9,10-tetracarboxylic acid is a chemical compound that belongs to the family of perylene dicarboxylic acids. It is a polycyclic aromatic hydrocarbon (PAH) that consists of four carboxylic acid groups attached to a perylene backbone. perylene-3,4,9,10-tetracarboxylic acid is used in various applications, including as a pigment in dyes, in the production of organic semiconductors, and as a fluorescent probe in biomedical research. Perylene-3,4,9,10-tetracarboxylic acid has also shown potential for use in organic photovoltaic devices and organic light-emitting diodes due to its high photoluminescence quantum yield and strong absorption in the visible region of the electromagnetic spectrum. Additionally, it has been studied for its potential as a pollutant and environmental contaminant, with researchers examining its sources, fate, and effects on ecosystems.

InChI:InChI=1/C24H12O8/c25-21(26)13-5-1-9-10-2-6-15(23(29)30)20-16(24(31)32)8-4-12(18(10)20)11-3-7-14(22(27)28)19(13)17(9)11/h1-8H,(H,25,26)(H,27,28)(H,29,30)(H,31,32)

Synthetic route

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With potassium hydroxide In water for 12h; Heating;	99%
Stage #1: perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride With potassium hydroxide In water at 20℃; for 6h; Stage #2: With hydrogenchloride In water pH=Ca. 7;	80%
With sodium hydroxide

1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic acid (118153-98-3) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With potassium hydroxide In ethylene glycol at 155 - 160℃; for 4h;	91%

1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid (107905-43-1) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With potassium hydroxide In ethylene glycol at 120℃; for 1h;	82%

dibenzo[cd,lm]perylene-1,3,8,10-tetraone → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With alkaline sodium hypochlorite
With chromium(III) oxide; sulfuric acid

3,10-diamino-dibenzo[cd,lm]perylene-1,8-dione (857785-32-1) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With potassium permanganate; sulfuric acid at 20℃;
With sodium dichromate; sulfuric acid at 20℃;

C32H18O (38250-80-5) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With nitric acid at 165 - 190℃;

1-Benzoyloxy-peropyren (21020-04-2) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With nitric acid at 180 - 200℃;

sulfuric acid (7664-93-9) + 3,4,9,10-perylene tetracarboxyxlic acid diimide (81-33-4) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
at 200℃;
at 200℃;

perylene-tetracarboxylic acid-(3.4.9.10)-diimide → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
With sulfuric acid at 200℃;

sulfuric acid (7664-93-9) + 3,10-diamino-dibenzo[cd,lm]perylene-1,8-dione (857785-32-1) + permanganate → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield

sulfuric acid (7664-93-9) + 3,10-diamino-2,9-dimethyl-dibenzo[cd,lm]perylene-1,8-dione + potassium permanganate → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield

sulfuric acid (7664-93-9) + 3,10-diamino-dibenzo[cd,lm]perylene-1,8-dione (857785-32-1) + sodium dichromate → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield

1,7-dichloroperylene-3,4,9,10-tetracarboxylic acid (118129-58-1) → perylene-3,4,9,10-tetracarboxylic acid (81-32-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent / Cl2, 3percent oleum / 9 h / 70 - 75 °C 2: 91 percent / KOH / ethane-1,2-diol / 4 h / 155 - 160 °C View Scheme

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → PERYLENE (198-55-0)

Conditions	Yield
With sodalime at 450 - 500℃; stream of superheated steam;	96%
bei der trocknen Destillation des Calciumsalzes;
With potassium hydroxide at 250℃; beim Erhitzen des Kaliumsalzes im Autoklaven;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + N,N-diethylethylenediamine (100-36-7) → N,N'-bis(2-(N'',N''-diethylamino)ethyl)perylene-3,4:9,10-bis(dicarboximide) (73528-90-2)

Conditions	Yield
In water Heating;	88%
1.) DMF, 145 deg C - 150 deg C, 1 h, 2.) 125 deg C - 140 deg C, 2 h; Yield given. Multistep reaction;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + benzyl chloride (100-44-7) → perylene 3,4,9,10-tetracarboxylic acid tetrabenzyl ester (698998-98-0)

Conditions	Yield
With dmap; 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;	86%

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → 1,12-sulfonyloxyperylene-3,4,9,10-tetracarboxylic acid (79750-27-9)

Conditions	Yield
	85%

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + N-butylamine (109-73-9) → 2,9-dibutylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (52000-75-6)

Conditions	Yield
With 1H-imidazole at 120℃; for 4h;	80%

4-aminobutyrylaldehyde diethylacetal (6346-09-4) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → N,N'-bis(4,4-diethoxybutyl)perylene-3,4,9,10-tetracarboxylic diimide (1446681-44-2)

Conditions	Yield
With 1H-imidazole at 120℃; for 4h;	78%

3,5-bis(benzyloxy)benzyl bromide (24131-32-6) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → tetrakis[3,5-di(benzyloxy)benzyl] 3,4,9,10-perylenetetracarboxylate

Conditions	Yield
With dmap; 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 85℃; for 12h;	76%

3-benzyloxybenzyl bromide (1700-31-8) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → tetrakis[3-(benzyloxy)benzyl] 3,4,9,10-perylenetetracarboxylate

Conditions	Yield
With dmap; 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 85℃; for 12h;	72%

copper(II) nitrate trihydrate + ethanol (64-17-5) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + ethylenediamine (107-15-3) → C32H44Cu2N8O10*3H2O*C2H6O

Conditions	Yield
In water at 20℃; for 0.5h;	72%

2-[2-(2-methoxyethoxy)ethoxy]ethylamine (74654-07-2) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → N,N'-di-[10-(3,6,9-trioxadecyl)]perylene-3,4,9,10-bis(dicarboximide)

Conditions	Yield
With 1H-imidazole; zinc diacetate at 160℃; for 18h; Inert atmosphere;	47%

titanium(IV) isopropylate (546-68-9) + 1,10-Phenanthroline (66-71-7) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → 2Ti(4+)*6C3H7O(1-)*2C12H8N2*C30H22O8(2-)*C3H8O

Conditions	Yield
In toluene at 40℃; for 144h; Inert atmosphere; Sealed tube;	38%

(2S,3S)-3-amino-4-{4,4’-dimethoxytrityloxy}butan-2-ol (956092-70-9) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + isopropylamine (75-31-0) → C52H42N2O8 (1260145-35-4)

Conditions	Yield
Stage #1: (2S,3S)-3-amino-4-{4,4’-dimethoxytrityloxy}butan-2-ol; perylene-3,4,9,10-tetracarboxylic acid With zinc diacetate; triethylamine In pyridine for 24h; Molecular sieve; Reflux; Stage #2: isopropylamine With zinc diacetate; triethylamine In pyridine for 24h; Molecular sieve; Reflux;	28%

7-amino-1,12-tridecadiene (1402226-20-3) + perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → N,N'-di(1,12-tridecadiene-7-yl)perylene-3,4,9,10,tetracarboxylic acid bisimide (1402226-21-4)

Conditions	Yield
With zinc diacetate In quinoline at 230℃; for 5h; Inert atmosphere;	12%

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + ethanolamine (141-43-5) → N-hydroxyethyl-3,4:9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide (80689-49-2)

Conditions	Yield
Stage #1: perylene-3,4,9,10-tetracarboxylic acid; ethanolamine In water at 0℃; for 5h; Reflux; Stage #2: With sulfuric acid In water at 90℃; for 0.5h;	10%

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + methylamine hydrochloride (593-51-1) → N,N'-Dimethylperylene-3,4,9,10-biscarboximide (5521-31-3)

Conditions	Yield
at 180 - 200℃;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → 3,4,9,10-perylene tetracarboxyxlic acid diimide (81-33-4)

Conditions	Yield
at 200 - 230℃; durch Erhitzen des Tetraammoniumsalzes mit Ammoniumcarbonat;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) → perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8)

Conditions	Yield
With acetic anhydride
With sodium hydroxide
With sulfuric acid at 20℃; for 12h;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + 4-chloro-aniline (106-47-8) → 3,4,9,10-perylenetetracarboxylic acid N,N'-di(4-chlorophenyl)diimide (2379-77-3)

Conditions	Yield
at 100 - 120℃;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + aniline (62-53-3) → 2,9-diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (128-65-4)

Conditions	Yield
With acetic acid at 100 - 120℃;
at 100 - 120℃;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + N,N-dimethylethylenediamine (108-00-9) → 2,9-bis(2-(dimethylamino)ethyl)anthra[2,1,9-def:6,5,10-d′e′f ′]-diisoquinoline-1,3,8,10(2H,9H)-tetraone (73528-89-9)

Conditions	Yield
1.) DMF, 145 deg C - 150 deg C, 1 h, 2.) 125 deg C - 140 deg C, 2 h; Yield given. Multistep reaction;

perylene-3,4,9,10-tetracarboxylic acid (81-32-3) + KOH-solution → PERYLENE (198-55-0) + Perylene-3-carboxylic acid (7350-88-1) + perylene-3,4,9-tricarboxylic acid + perylene-dicarboxylic acid-(3.9 or 3.10)

Conditions	Yield
at 190 - 250℃; im Autoklaven;

Upstream product

• 38250-80-5 C₃₂H₁₈O 
• 21020-04-2 1-Benzoyloxy-peropyren 
• 118129-58-1 1,7-dichloroperylene-3,4,9,10-tetracarboxylic acid 
• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 
• 7664-93-9 sulfuric acid 
• 857785-32-1 3,10-diamino-dibenzo[cd,lm]perylene-1,8-dione 
• 107905-43-1 1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid 
• 118153-98-3 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic acid 
• 81-33-4 3,4,9,10-perylene tetracarboxyxlic acid diimide 

Downstream Products

• 198-55-0 PERYLENE 
• 7350-88-1 Perylene-3-carboxylic acid 
• 698998-98-0 perylene 3,4,9,10-tetracarboxylic acid tetrabenzyl ester 
• 73528-84-4 Bis-(dimethylaminoethylimido)-perylene 1,6,7,12-tetracarboxylic acid benzenesulfomethylate 
• 73528-86-6 Bis-(diethylaminoethylimido)-perylene 1,6,7,12-tetracarboxylic acid benzenesulfoethylate 
• 52000-75-6 N¹,N²-bis(1-butyl)perylene-3,4,9,10-tetracarboxylic diimide 
• 128-65-4 2,9-diphenylanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone 
• 2379-77-3 3,4,9,10-perylenetetraracarboxylic acid N,N′-di(4-chlorophenyl)diimide 
• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 
• 81-33-4 3,4,9,10-perylene tetracarboxyxlic acid diimide 
• 5521-31-3 N,N'-Dimethylperylene-3,4,9,10-biscarboximide 

Relevant articles and documents

The role of reducing agent in perylene tetracarboxylic acid coating on graphene sheets enhances Pd nanoparticles-electrocalytic ethanol oxidation

New catalysts, consisting of perylene tetracarboxylic acid functionalized graphene sheets support-enhanced electrocatalytic Pd nanoparticles (Pd/PTCA-GS), were fabricated using different reducing agents, including H2, NaBH4 and ethylene glycol (EG). The graphene sheets (GS) were functionalized via π-π stacking and hydrophobic forces. The information of the morphologies, sizes, and dispersion of Pd nanoparticles (NPs) for the as-prepared catalysts was verified by transmission electron microscopy (TEM), high-resolution transmission electron microscopy (HRTEM), Raman spectra and X-ray diffraction (XRD). As the ethanol electro-oxidation anode catalysts, the new catalysts exhibited better kinetics, higher electrocatalytic activity, better tolerance and better electrochemical stability than the Pd/GS and Pd/C, which illustrated that the new catalysts had potential applications in direct ethanol alkaline fuel cells (DEAFCs). Most attractively, the role of the chemical reduction methods (the NaBH4, EG and H2 as reducing agents) were studied systematically for the ethanol electro-oxidation anode catalysts in DEAFCs. As expected, the chemical reduction method remarkably affected the electrochemical behavior. Among all the Pd/PTCA-GS catalysts tested, Pd/PTCA-GS(NaBH4) exhibited the highest catalytic activity and stability, which may be due to the Pd NPs for Pd/PTCA-GS(NaBH4) having a narrow size distribution, uniform distribution and more perfect crystal structure than that of other as-prepared nanocomposites. These Pd/PTCA-GS are promising catalysts for developing a highly efficient direct ethanol alkaline fuel cells system for power applications. The Royal Society of Chemistry 2013.

Dual-responses for electrochemical and electrochemiluminescent detection based on a bifunctional probe

A bifunctional probe (PTC-Tb) which acts as not only a well-defined and stable electrochemical redox molecule but also as a highly efficient co-reactant of an electrochemiluminescent oxygen-peroxydisulfate system was firstly synthesized and applied to the construction of dual-response aptasensors for thrombin detection. The Royal Society of Chemistry 2014.

Guidance from an in situ hot stage in TEM to synthesize magnetic metal nanoparticles from a MOF

A series of in situ hot stage experiments using transmission electron microscopy (TEM) were studied to directly observe the transition of a Ni-MOF to Ni nanoparticles wrapped in carbon (Ni-NPC) over temperatures ranging from ambient temperature to 700 °C. Ni-NPC-600 displays high catalytic activity in 4-nitrophenol reduction and high conversion, even after 10 cycles.

New perylene-based non-conventional discotic liquid crystals

The synthesis, optical properties and thermal behaviour of three novel non-conventional 3,4,9,10-tetrasubstituted perylene-based discotic oligomers are reported for the first time consisting of a perylene core attached to which are four 4-cyanobiphenyl, triphenylene and cholesteryl units via flexible alkyl spacers. All the oligomers self-assemble into a mesophase and exhibit excellent fluorescence emission properties making them suitable for various opto-electronic applications. The Royal Society of Chemistry 2013.

A long-range emissive mega-Stokes inorganic-organic hybrid material with peripheral carboxyl functionality for As(v) recognition and its application in bioimaging

We demonstrate a strategy for the recognition of As5+ in aqueous solution using a red-emissive probe based on a perylene-Cu2+ ensemble decorated with peripheral free carboxyl functionality. Single crystal analysis helped us to understand the chemical structure of the probe. To the best of our knowledge, this is the first probe for arsenic detection which emits in the red region (λem = 600 nm). The perylene-Cu2+ ensemble exhibited a mega-Stokes shift (>100 nm) with a high degree of selectivity upon interaction with As5+, which indicated that the present probe has the potential to be used as a turn-on optical sensor for selective detection of As5+ with fewer experimental limitations. The detection limit was found to be 26 nM. Inspired by its good emissive properties, the ensemble was further explored for imaging As5+ in live cells. Because of its long-range emissive nature, no autofluorescence from the cellular species was observed during the imaging process. The probe was evaluated to be non-toxic and successfully permeated the cell membrane without the help of any permeabilizing agent to image As5+.

Columnar Self-Assembly of Electron-Deficient Dendronized Bay-Annulated Perylene Bisimides

Three new heteroatom bay-annulated perylene bisimides (PBIs) have been synthesized by microwave-assisted synthesis in excellent yield. N-annulated and S-annulated perylene bisimides exhibited columnar hexagonal phase, whereas Se-annulated perylene bisimide exhibited low temperature columnar oblique phase in addition to the high temperature columnar hexagonal phase. The cup shaped bay-annulated PBIs pack into columns with enhanced intermolecular interactions. In comparison to PBI, these molecules exhibited lower melting and clearing temperature, with good solubility. A small red shift in the absorption was seen in the case of N-annulated PBI, whereas S- and Se-annulated PBIs exhibited blue-shifted absorption spectra. Bay-annulation increased the HOMO and LUMO levels of the N-annulated perylene bisimide, whereas a slight increase in the LUMO level and a decrease in the HOMO levels were observed in the case of S- and Se-annulated perylene bisimides, in comparison to the simple perylene bisimide. The band gaps of PBI and PBI-N were almost same, whereas an increase in the band gaps were observed in the case of S- and Se-annulated PBIs. The tendency to freeze in the ordered glassy columnar phase for PBI-N and PBI-S will help to overcome the charge traps due to crystallization, which are detrimental to one-dimensional charge carrier mobility. These solution processable electron deficient columnar semiconductors possessing good thermal stability may form an easily accessible promising class of n-type materials.