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932221

Sigma-Aldrich

1,4,5,8-Naphthalenetetracarboxylic dianhydride

≥98%

Synonym(s):

6,13-Dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone, Isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone, NTDA, Naphthalene-1,4,5,8-tetracarboxylic dianhydride, NTCDA

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About This Item

Empirical Formula (Hill Notation):
C14H4O6
CAS Number:
81-30-1
Molecular Weight:
268.18
Beilstein:
272788
MDL number:
MFCD00006915
UNSPSC Code:
12352005
NACRES:
NA.23

grade

sublimed grade

Quality Level

100

Assay

≥98 (elemental analysis)
≥98%

loss

0.5% TGA, > 270 °C (weight loss)

mp

>300 °C (lit.)

solubility

dichloromethane: soluble

fluorescence

λem 392 nm±10 nm in dichloromethane

λ

in dichloromethane

UV absorption

λ: 366 nm±5 nm Amax

SMILES string

O=C1OC(=O)c2ccc3C(=O)OC(=O)c4ccc1c2c34

InChI

1S/C14H4O6/c15-11-5-1-2-6-10-8(14(18)20-12(6)16)4-3-7(9(5)10)13(17)19-11/h1-4H

InChI key

YTVNOVQHSGMMOV-UHFFFAOYSA-N

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Application

1,4,5,8-Naphthalenetetracarboxylic dianhydride, also known as NTCDA or NTCDA-DA, 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.
1,4,5,8-Naphthalenetetracarboxylic dianhydride, also known as NTDA or NTCDA, is an organic compound related to naphthalene. NTDA is most commonly used as a precursor to naphthalenediimides (NDIs) (such as napthalenetetracarboxylic diimide), which has many uses, especially in energy harvesting and storage. NTCDA is used in electrode interface for organic photovoltaics, selective adsorption and to fabricate copolyimides to use in membranes for gas separation and for enhanced proton exchange membranes in fuel cells.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Understanding the Electrochemical Properties of Naphthalene Diimide: Implication for Stable and High-Rate Lithium-Ion Battery Electrodes
Shi, Y. et al.
Chemistry of Materials, 30, 3508-3517 (2018)
Direct Solar-to-Electrochemical Energy Storage in a Functionalized Covalent Organic Framework
Lv, J. et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 57, 12716-12720 (2018)
Novel sulfonated polyimide-nafion nanocomposite membranes: Fabrication, morphology and physiochemical investigations for fuel cell applications
Ali, N. et al.
Journal of Molecular Structure, 1231, 129940-129940 (2021)
Six-membered ring copolyimides as novel high performance membrane materials for gas separations
Qian, Kai, et al.
Materials Today Communications, 14, 254-262 (2018)
A Crystalline Polyimide Porous Organic Framework for Selective Adsorption of Acetylene over Ethylene
Jiang, L. et al.
Journal of the American Chemical Society, 140, 15724-15730 (2018)
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