1,4,5,8-Naphthalenetetracarboxylic dianhydride Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

371.34°C (rough estimate)

Density 

1.5122 (rough estimate)

refractive index 

1.5230 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly, Heated), Methanol (Slightly)

form 

Solid

color 

Off-White to Light Beige

semiconductor properties

N-type (mobility=0.003cm2/V·s)

Sensitive 

Moisture Sensitive

BRN 

272788

Stability:

Hygroscopic, Moisture Sensitive

InChIKey

YTVNOVQHSGMMOV-UHFFFAOYSA-N

CAS DataBase Reference

81-30-1(CAS DataBase Reference)

NIST Chemistry Reference

1,4,5,8-Naphthalenetetracarboxylic dianhydride(81-30-1)

EPA Substance Registry System

[2]Benzopyrano[6,5,4-def][2]benzopyran-1,3,6,8-tetrone (81-30-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

QK3695000

F 

10-21

TSCA 

Yes

HS Code 

29173990

Toxicity

LD50 oral in rat: 7400mg/kg

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,4,5,8-Naphthalenetetracarboxylic dianhydride Usage And Synthesis

Uses

1,4,5,8-Naphthalenetetracarboxylic Dianhydride is used as a reagent in the preparation of novel fluorescent markers for hypoxic cells of naphthalimides with two heterocyclic side chains for bioreductive binding.

Description

1,4,5,8-Naphthalenetetracarboxylic dianhydride (NTCDA) has a naphthalene core with four carboxylic acids at the 1, 4, 5, and 8 positions, with each adjacent carboxylic acid forming an anhydride. NTCDA is aromatic, stable, planar, and highly symmetric chemically, and also possesses favourable electrical properties. Due to the electron-deficient nature of the carboxyl group, NTCDA is known to be a strong electron acceptor molecule with an electron affinity as high as 4.0 eV. It has been demonstrated that NTCDA significantly improves the electrical conductivity of co-deposited thin films of NTCDA and a wide range of metals including indium, magnesium and aluminium. The high electron conductivity of co-deposited NTCDA/In films also strongly suggests that co-deposited NTCDA/In films are excellent electron transport layers for organic light emitting diodes and photovoltaic devices.

Chemical Properties

Light brown solid

Uses

1,4,5,8-Naphthalenetetracarboxylic Dianhydride is used as a reagent in the preparation of novel fluorescent markers for hypoxic cells of naphthalimides with two heterocyclic side chains for bioreductive binding.

Uses

NTCDA can be used in the fabrication of a variety of devices such as fuel cells, thin film transistors (OTFTs), lithium ion batteries, and organic photovoltaics (OPV).

General Description

1,4,5,8-Naphthalenetetracarboxylic dianhydride (NTCDA) is a tetrafunctional monomer that can be used as an electron transporting material in organic electronics.

Materials Uses

1,4,5,8-Naphthalenetetracarboxylic dianhydride is commonly used as a building block or precursor for the synthesis of organic semiconducting materials. These materials can be employed in various organic electronic devices, including organic field-effect transistors (OFETs), organic photovoltaic (OPV) devices and organic photodetectors. NTCDA can be utilized as an electron-accepting material or an anchoring unit in studies on dye-sensitized solar cells (DSSCs) for enhancing the photovoltaic performance of the device.

Synthesis

General procedure: 100.0 g of a mixture consisting of 1,4,5,8-naphthalenetetracarboxylic acid and 1,4,5,8-naphthalenetetracarboxylic acid monoanhydride (mass ratio 86:14) was added to a 1000 mL three-necked flask with 200 mL of N,N-dimethylacetamide and 400 mL of toluene as solvent. The mixture was heated to 111 °C under nitrogen protection and the reaction was stirred at this temperature for 2 hours. After completion of the reaction, the reaction solution was cooled to 10 °C and stirring was continued for 1 hour. Subsequently, the precipitate was collected by filtration to afford 73 g of 1,4,5,8-naphthalenetetracarboxylic dianhydride.

References

[1] Patent: US2016/376285, 2016, A1. Location in patent: Paragraph 0113

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