22291-04-9

Basic information

• Product Name: naphthalene diimide
• Synonyms: naphthalene diimide;2,7-Bis[2-(dimethylamino)ethyl]benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone;N,N'-Bis[2-(dimethylamino)ethyl]-1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-diimide;2,7-Bis(2-(dimethylamino)ethyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone;N,N'-Bis[2-(dimethylamino)ethyl]-1,8:4,5-naphthalenetetracarboxdiimide;N,N'-Bis[2-(dimethylamino)ethyl]-1,8:4,5-naphthalenetetracarboxdiimide
• CAS NO: 22291-04-9
• Molecular Formula: C22H24N4O4
• Molecular Weight: 408.45036
• Mol File: 22291-04-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 231.0 to 235.0 °C
• Boiling Point: 590.8°Cat760mmHg
• Flash Point: 263.1°C
• Appearance: /
• Density: 1.336
• Vapor Pressure: 6.23E-14mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: naphthalene diimide(CAS DataBase Reference)
• NIST Chemistry Reference: naphthalene diimide(22291-04-9)
• EPA Substance Registry System: naphthalene diimide(22291-04-9)

Safety Data

• Hazardous Substances Data: 22291-04-9(Hazardous Substances Data)

Usage

General Description

Naphthalene diimide (NDI) is a chemical compound that consists of two naphthalene rings linked by two imide groups. It is a bright yellow solid with excellent thermal and chemical stability, making it a popular building block for various organic semiconductors and functional materials. NDI derivatives have been extensively studied for their potential applications in organic electronics, such as organic photovoltaics, organic field-effect transistors, and organic light-emitting diodes. They exhibit high electron affinity, good charge transport properties, and strong absorption in the visible region, making them promising candidates for efficient electron-transporting materials in optoelectronic devices. NDI derivatives have also been investigated for their use in rechargeable lithium-ion batteries, where they have shown great potential as high-performance electrode materials. Overall, NDI and its derivatives hold great promise for a wide range of applications in the field of organic electronics and functional materials.

InChI:InChI=1/C22H24N4O4.2BrH/c1-23(2)9-11-25-19(27)13-5-7-15-18-16(8-6-14(17(13)18)20(25)28)22(30)26(21(15)29)12-10-24(3)4;;/h5-8H,9-12H2,1-4H3;2*1H

Upstream product

• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 108-00-9 N,N-dimethylethylenediamine 
• 383413-13-6 O-dimethoxytrityl-2-dimethyl-3-hydroxypropyl amine 
• 104-10-9 2-(4'-aminophenyl)ethyl alcohol 
• 83204-68-6 2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride 

Relevant articles and documents

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Spectroscopic and structural characterization of the charge-transfer interaction of N,N′-bis-alkyl derivatives of 1,4,6,8-naphthalenediimide with chloranilic and picric acids

Charge-transfer (CT) complexes formed from the reactions of two N,N′-bis-alkyl derivatives of 1,4,6,8-naphthalenediimide such as N,N′-bis[2-hydroxyethyl)]-1,4,6,8-naphthalenediimide (BHENDI) and N,N′-bis-[2-N,N-dimethylaminoethyl)]-1,4,6,8-naphthalenediimide (BDMAENDI) with chloranilic acid (CLA) and piciric acid (PA) as π-acceptors, have been studied spectrophotometrically in methanol and chloroform, respectively at 25 °C. The photometric titration curves for the reactions indicated that the data obtained refer to 1:1 charge-transfer complexes of [(BHENDI)(CLA)], [(BDMAENDI)(CLA)], [(BHENDI)(PA)] and [(BDMAENDI)(PA)] were formed. Benesi-Hildebrand and its modification methods were applied to the determination of association constant (K), molar extinction coefficient (ε). The solid CT complexes have been synthesized and characterization by different spectral methods.

Spectral properties of new N,N′-bis-alkyl-1,4,6,8-naphthalenediimide complexes

The photophysical properties of two N,N′-bis-alkyl-1,4,6,8-naphthalenediimide (DCN1 and DCN2) have been studied in chloroform and N,N-dimethylformamide solvents. The ability of DCN2 in N,N-dimethylformamide to detect metal cations have been monitored by the fluorescence emission spectroscopy. It has been shown that the fluorescent intensity is very sensitive to the concentration of Fe3+ cations. The reaction of iodine with N,N′-bis-alkyl-1,4,6,8-naphthalenediimide in chloroform solution have been investigated by spectrophotometric method. The results indicate the formation of two CT-complexes [(DCN1)I]+·I3- and [(DCN2)I]+·I3- at donor:acceptor molar ratio of 1:2. The [(DCN1)I]+·I3- shows the characteristic absorptions of I3- ion at 290 and 360 nm while the charge-transfer transition of [(DCN2)I]+·I3- occurs at 310 nm. Three characteristic bands at the far infrared region in each iodine complex are observed around 135, 105 and 85 cm-1 due to νas (I-I), νs (I-I) and δ (I3-), respectively with C2v symmetry. The values of the complex formation constant, K, and the absorptivity, ε have been calculated.

Aqueous Phase Phosphorescence: Ambient Triplet Harvesting of Purely Organic Phosphors via Supramolecular Scaffolding

Ambient solution and amorphous state room temperature phosphorescence (RTP) from purely organic chromophores is rarely achieved. Remarkable stabilization of triplet excitons is realized to obtain deep red phosphorescence in water and in amorphous film state under ambient conditions by a unique supramolecular hybrid assembly between inorganic laponite clay and heavy atom core substituted naphthalene diimide (NDI) phosphor. Structural rigidity and oxygen tolerance of the inorganic template along with controlled molecular organization via supramolecular scaffolding are envisaged to alleviate the unprecedented aqueous phase phosphorescence.

NAPHTHALENE DIIMIDE COMPOUNDS INTERACTING WITH G-QUADRUPLEX REGIONS IN DNA

The invention relates to novel compounds which are naphthalene diimides of general formula (I). The compounds are used in therapy, particularly in cancer treatment.