Naphthalene-1,4,5,8-tetracarboxylic Dianhydride

Name: Naphthalene-1,4,5,8-tetracarboxylic Dianhydride
SKU: ACM81301-3
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Catalog NumberACM81301-3

CAS Number81-30-1

CategoryOrganic Field Effect Transistor (OFET) Materials; Monomers; Polymers

Naphthalene-1,4,5,8-tetracarboxylic Dianhydride

IUPAC Name

6,13-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone

Molecular Weight

268.18g/mol

Molecular Formula

C14H4O6

Canonical SMILES

C1=CC2=C3C(=CC=C4C3=C1C(=O)OC4=O)C(=O)OC2=O

InChI

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

Application

Naphthalene-1,4,5,8-tetracarboxylic dianhydride serves as a versatile component in the creation of various electronic and energy devices, including fuel cells, thin film transistors, lithium-ion batteries, and organic photovoltaics. The compound features a naphthalene core with four strategically placed carboxylic acids that form anhydrides, lending the molecule its aromatic, stable, and highly symmetric chemical nature along with favorable electrical characteristics. Notably, the electron-deficient carboxyl groups make it a potent electron acceptor with an electron affinity of up to 4.0 eV. Naphthalene-1,4,5,8-tetracarboxylic dianhydride enhances the electrical conductivity of thin films co-deposited with various metals, such as indium, magnesium, and aluminum. This high electron conductivity, particularly in films co-deposited with indium, signifies its potential as an outstanding electron transport layer in organic light-emitting diodes and photovoltaic devices.

Complexity

446

Covalently-Bonded Unit Count

EC Number

201-342-5

Exact Mass

268.000788g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

1,4,5,8-naphthalenetetracarboxylic 1,8:4,5 dianhydride;naphthalenetetracarboxylic dianhydride;NTA dianhydride

Monoisotopic Mass