3,4,9,10-Perylenetetracarboxylic Diimide

Base Information

• Chemical Name: 3,4,9,10-Perylenetetracarboxylic Diimide
• CAS No.: 81-33-4
• Deprecated CAS: 12236-71-4,1039727-78-0
• Molecular Formula: C24H10N2O4
• Molecular Weight: 390.354
• Hs Code.: 29337900
• European Community (EC) Number: 201-344-6,602-653-2
• NSC Number: 16842
• UNII: 63NLI8842L
• DSSTox Substance ID: DTXSID9052555
• Nikkaji Number: J39.760A
• Wikipedia: Pigment_Violet_29
• Wikidata: Q16948010
• Metabolomics Workbench ID: 58374
• Mol file: 81-33-4.mol

Synonyms:perylenediimide

Chemical Property of 3,4,9,10-Perylenetetracarboxylic Diimide

Chemical Property:

• Appearance/Colour: Amaranthine uniform powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.88
• Boiling Point: 821.4 °C at 760 mmHg
• PKA: 8.75±0.20(Predicted)
• Flash Point: 314 °C
• PSA: 99.86000
• Density: 1.68 g/cm³
• LogP: 3.01620
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Sulfuric Acid (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 390.06405680
• Heavy Atom Count: 30
• Complexity: 735

Purity/Quality:

99% ^*data from raw suppliers

3,4,9,10-PerylenetetracarboxylicDiimide(~85%) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=CC=C4C3=C1C5=C6C4=CC=C7C6=C(C=C5)C(=O)NC7=O)C(=O)NC2=O
• General Description: 3,4,9,10-Perylenetetracarboxylic diimide (PTCDI or PDI) is a highly stable and fluorescent chromophore, widely recognized for its strong fluorescence in organic solvents but prone to aggregation and fluorescence quenching in aqueous environments. To address this limitation, researchers have functionalized PDI with cationic dendrimers, enhancing its water solubility and optical properties for applications in biological imaging and gene transfection. These modified PDIs exhibit rapid cellular uptake, high transfection efficiency, and low cytotoxicity, making them promising candidates for gene therapy and other biomedical applications.

Technology Process of 3,4,9,10-Perylenetetracarboxylic Diimide

There total 11 articles about 3,4,9,10-Perylenetetracarboxylic Diimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1,8-Naphthalimide (81-83-4) → 3,4,9,10-perylene tetracarboxyxlic acid diimide (81-33-4)

Guidance literature:

With 2,6-dichloro-benzonitrile; potassium tert-butylate; In diethylene glycol dimethyl ether; at 130 ℃; for 1h; Further Variations:; Reaction partners; Solvents; Temperatures; Product distribution;

DOI:10.1021/jo0010835

Reference yield: 95.0%

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → 3,4,9,10-perylene tetracarboxyxlic acid diimide (81-33-4)

Guidance literature:

With ammonium hydroxide; In ethanol; for 4h; Reflux;

Reference yield: 21.0%

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → perylene-3,4,9,10-tetracarboxylic-3,4-anhydride-9,10-carboxamide (33955-42-9) + 3,4,9,10-perylene tetracarboxyxlic acid diimide (81-33-4)

Guidance literature:

With ammonium hydroxide; In water; at 90 ℃; for 2h;

DOI:10.1016/j.tet.2008.02.104

upstream raw materials:

1,8-Naphthalimide

perylene-3,4,9,10-tetracarboxylic acid

1,3,1',3'-Tetraoxo-2,3,2',3'-tetrahydro-1H,1'H-[6,6']bi[benzo[de]isoquinolinyl]-7,7'-dicarboxylic acid

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Downstream raw materials:

perylene-3,4,9,10-tetracarboxylic acid

N,N'-bis(cyclohexyl)perylene-3,4,9,10-tetracarboxylic acid diimide

N-2-[(2-O-4,4′-dimethoxytritylethoxy)ethyl]-N′-2-(2-hydroxyethoxy)ethyl-3,4,9,10-perylenetetracarboxylic diimide

bis(2,6-diisopropylphenyl)-5,6,12,13-tetraphenoxyanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H, 9H)-tetraone

Refernces

Fluorescent water-soluble perylenediimide-cored cationic dendrimers: Synthesis, optical properties, and cell uptake

10.1039/c3cc40330k

The research aimed to synthesize and investigate the optical properties of water-soluble, perylenediimide-cored cationic dendrimers with peripheral amine groups, designed for potential applications in gene transfection and biological imaging. The purpose was to enhance the water solubility and fluorescence of perylenediimides (PDIs), which are known for their stability and high fluorescence in organic solvents but aggregate and become less fluorescent in water. The researchers synthesized different generations of PDI-cored dendrimers, which were characterized by a central fluorescent PDI chromophore, degradable dendritic polyesters, and peripheral primary amines that provided positive charges after treatment with dilute hydrochloric acid. The chemicals used in the synthesis process included amine-functionalized PDI, 2-methacryloyloxyethyl acrylate (MAEA), cysteamine (CA), and dimethyl sulfoxide (DMSO) as an accelerator. The study concluded that increasing the dendrimer generation enhanced gene transfection efficiency, with the highest efficiency observed in the third-generation dendrimer (G3), attributed to its larger outer branches and more positive charges. These dendrimers demonstrated rapid internalization into live cells, high gene transfection efficacy, and low cytotoxicity, making them promising candidates for gene therapy applications.