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932760

Sigma-Aldrich

3,4,9,10-Perylenetetracarboxylic dianhydride

Synonyme(s) :

PTCDA, Perylenetetracarboxylic acid dianhydride, Perylene-3,4,9,10-tetracarboxylic dianhydride, Pigment Red 224

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About This Item

Formule empirique (notation de Hill):
C24H8O6
Numéro CAS:
128-69-8
Poids moléculaire :
392.32
Numéro Beilstein :
57831
Numéro MDL:
MFCD00006916
Code UNSPSC :
12352103
Nomenclature NACRES :
NA.21

Pureté

99% (sublimed)

Niveau de qualité

100

Pf

>300 °C

Solubilité

DMSO: slightly soluble

Énergie orbitale

HOMO 5.85 eV 
LUMO 3.9 eV 

InChI

1S/C24H8O6/c25-21-13-5-1-9-10-2-6-15-20-16(24(28)30-23(15)27)8-4-12(18(10)20)11-3-7-14(22(26)29-21)19(13)17(9)11/h1-8H

Clé InChI

CLYVDMAATCIVBF-UHFFFAOYSA-N

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Application

3,4,9,10-Perylenetetracarboxylic dianhydride, also known as Perylenetetracarboxylic acid dianhydride, is a large π-conjugated semiconductor aromatic organic molecule. It is an organic dye molecule and an organic semiconductor. It is used as a precursor to a class of molecules known as Rylene dyes, which are useful as pigments and dyes. It is a dark red solid with low solubility in aromatic solvents.
The compound has attracted much interest as an organic semiconductor. It has potential applications in organic and molecular electronics, and typically used as an archetype molecular compound. PTCDA shares many properties with conventional semiconductors (with their delocalized electronic states), and insulator-like organic molecular crystals (OMCs) (with their large absorption oscillator strengths, excitonic self-trapping, polaron-assisted conduction, etc.). That is due to extremely close π-π stacking, an unusually small intermolecular distance of only 3.21 A. Among its applications, it is important to highlight the latest focus on environment monitoring, self-assembly and photocatalysis.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

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Self-assembled perylene diimide based supramolecular heterojunction with Bi2WO6 for efficient visible-light-driven photocatalysis
Zhang, Kai, et al.
Applied Catalysis. B, Environmental, 232, 175-181 (2018)
Kangyi Kong et al.
Chemical communications (Cambridge, England), 55(56), 8090-8093 (2019-06-25)
In this communication, a self-assembled supramolecular system consisting of phosphoric acid substituted perylene diimide (P-PMPDI) has been successfully developed for highly efficient photocatalytic hydrogen evolution. Compared with a carboxylic substituent perylene diimide (P-CMPDI), P-PMPDI showed a superior H2 evolution reaction
Weiqin Wei et al.
Small (Weinheim an der Bergstrasse, Germany), 15(49), e1903933-e1903933 (2019-10-28)
A semi-core-shell structure of perylene diimide (PDI) self-assembly coated with TiO2 nanoparticles is constructed, in which nanoscale porous TiO2 shell is formed and PDI self-assembly presented 1D structure. A full-spectrum photocatalyst is obtained using this structure to resolve a conundrum-TiO2
Mohammad Rezwan Habib et al.
Nanoscale, 10(34), 16107-16115 (2018-08-17)
We report the photoluminescence (PL) characteristics of a van der Waals (vdW) heterojunction constructed by simply depositing an organic semiconductor of 3,4,9,10-perylene tetracarboxylic dianhydride (PTCDA) onto a two-dimensional MoS2 monolayer. The crystallinity of PTCDA on MoS2 is significantly improved due
Zijian Zhang et al.
Advanced materials (Deerfield Beach, Fla.), 32(32), e1907746-e1907746 (2020-07-01)
A highly crystalline perylene imide polymer (Urea-PDI) photocatalyst is successfully constructed. The Urea-PDI presents a wide spectrum response owing to its large conjugated system. The Urea-PDI performs so far highest oxygen evolution rate (3223.9 µmol g-1 h-1 ) without cocatalysts
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