Pyrene-4,5-dione

CAS Number 6217-22-7

Covalent Organic Frameworks (COFs) Pyrene Ligand

A 1,2-diketone bridging ligand linker for COFs in application of light-emitting diodes and photovoltaics

Overview
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Pyrene-4,5-dione (PDO), CAS number 6217-22-7, bearing a 1,2-dione functional group, is an oxidised polycyclic aromatic hydrocarbon (PAH) pyrene. Pyrene is attractive for its photophysical properties including delayed appearance of fluorescence, obvious solvent discoloration, and a high tendency to form active excimer.

9-Phenyl-10-(4-(pyren-1-yl)phenyl)-9H-pyreno[4,5-d]imidazole (PyPI-Py), prepared by using pyrene-4,5-dione as one of the starting materials, is a highly efficient blue light-emitting material. Non-doped blue OLED based on PyPI-Py as the active layer material exhibited excellent performance with a maximum brightness of 75,687 cd m⁻² , a maximum current efficiency of 13.38 cd A⁻¹, and a maximum external quantum efficiency (η_ext ) of 8.52%. Moreover, the η_ext is maintained at 8.35% and 8.05% at a brightness of 10,000 and 50,000 cd m⁻², respectively.

Pyrene-4,5-dione is also a basic building block for constructing covalent organic frameworks (COFs) to form pyrene-fused pyrazaacenes in organic electronic applications.

MOF and COF ligands

1,2-diketone ligand for cross-linked COF networks

Worldwide shipping

Quick and reliable shipping

High purity

>97% High purity

Facile reactions

Readily for amination reactions

General Information

CAS Number	6217-22-7
Chemical Formula	C₁₆H₈O₂
Full Name	Pyrene-4,5-dione
Molecular Weight	232.24 g/mol
Synonyms	4,5-Pyrenedione, PDO Pyrene-4,5-quinone 4,5-Pyrenequinone
Classification / Family	Pyrenes, COF ligands, Light-emitting diodes

Chemical Structure

Product Details

Purity	>97%
Melting Point	310 °C
Appearance	Light yellow to yellow to orange powder/crystals

MSDS Documentation

Pyrene-4,5-dione MSDS Sheet

Literature and Reviews

Highly Efficient Blue Organic Light-Emitting Diode Based on a Pyrene[4,5-d]Imidazole-Pyrene Molecule, Y. Liu et al., CCS Chem., 4, 214–227 (2022); DOI: 10.31635/ccschem.021.202000627.
A supramolecular strategy based on molecular dipole moments for high-quality covalent organic frameworks, L. Salonen et al., Chem. Commun., 52, 7986-7989 (2016); DOI: 10.1039/C6CC02170K.
Functionalization of Pyrene To Prepare Luminescent Materials—Typical Examples of Synthetic Methodology, X. Feng et al., Chem. Eur. J., 22 (34), 11898-11916 (2016); DOI: 10.1002/chem.201600465.
Synthesis and Excimer Formation Properties of Electroactive Polyamides Incorporated with 4,5-Diphenoxypyrene Units, S. Chen et al., Polymers, 14, 261 (2022); DOI: 10.3390/polym14020261.
Nickel(ii) complexes bearing 4,5-bis(arylimino)pyrenylidenes: synthesis, characterization, and ethylenepolymerization behaviour, K. Song et al., Dalton Trans., 42, 9166-9175 (2013); DOI: 10.1039/C2DT32343E.
Building Blocks and COFs Formed in Concert—Three-Component Synthesis of Pyrene-Fused Azaacene Covalent Organic Framework in the Bulk and as Films, L. Frey et al., Angew. Chem. Int. Ed., 62 (30), e202302872 (2023); DOI: 10.1002/anie.202302872.

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