naphthalene diimide

Base Information

• Chemical Name: naphthalene diimide
• CAS No.: 22291-04-9
• Molecular Formula: C₂₂H₂₄N₄O₄
• Molecular Weight: 408.457
• Mol file: 22291-04-9.mol

Synonyms:1,4,5,8-Naphthalenetetracarboxylic1,8:4,5-diimide, N,N'-bis[2-(dimethylamino)ethyl]- (8CI)

Chemical Property of naphthalene diimide

Chemical Property:

• Vapor Pressure: 6.23E-14mmHg at 25°C
• Melting Point: 231.0 to 235.0 °C
• Boiling Point: 590.8°Cat760mmHg
• Flash Point: 263.1°C
• PSA: 84.62000
• Density: g/cm³
• LogP: 0.18880
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

N,N'-Bis[2-(dimethylamino)ethyl]-1,8:4,5-naphthalenetetracarboxdiimide >98.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Naphthalene diimide (NDI) derivatives are aromatic compounds known for their conductive properties, making them valuable in molecular electronics. Their ability to facilitate charge transfer can be modulated by factors such as linker length, distal substituents, and structural incorporation within supramolecular assemblies, as demonstrated in cyclic peptide-based systems. These properties enable the engineering of tunable conductive materials.

Technology Process of naphthalene diimide

There total 5 articles about naphthalene 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: 92.0%

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) + N,N-dimethylethylenediamine (108-00-9) → N,N'-bis[(2-N,N-dimethylaminoethyl)]-1,4,6,8-naphthalene diimide (22291-04-9)

Guidance literature:

In tetrahydrofuran; for 8h; Heating;

DOI:10.1016/S0968-0896(01)00108-0

Reference yield: 25.0%

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) + N,N-dimethylethylenediamine (108-00-9) + O-dimethoxytrityl-2-dimethyl-3-hydroxypropyl amine (383413-13-6) → N,N'-bis[(2-N,N-dimethylaminoethyl)]-1,4,6,8-naphthalene diimide (22291-04-9) + N-(O-dimethoxytrityl-2-dimethyl-3-hydroxypropyl)-N'-[2-(N,N-dimethylamino)-ethyl]-1,4,5,8-naphtalene tetracarboxylic diimide + 2,7-bis-{3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2,2-dimethyl-propyl}-benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone

Guidance literature:

In isopropyl alcohol; Heating;

DOI:10.1016/S0968-0896(01)00135-3

Reference yield: 20.0%

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) + N,N-dimethylethylenediamine (108-00-9) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → N,N'-bis[(2-N,N-dimethylaminoethyl)]-1,4,6,8-naphthalene diimide (22291-04-9) + N-[4-(2-hydroxyethyl)phenyl]-N'-[2-(N,N-dimethylamino)ethyl]-1,4,5,8-naphthalene tetracarboxylic diimide + 2,7-bis-[4-(2-hydroxy-ethyl)-phenyl]-benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone

Guidance literature:

With pyridine; zinc diacetate; Heating;

DOI:10.1016/S0968-0896(01)00135-3

upstream raw materials:

1,4,5,8-naphthalenetetracarboxylic dianhydride

N,N-dimethylethylenediamine

O-dimethoxytrityl-2-dimethyl-3-hydroxypropyl amine

2-(4'-aminophenyl)ethyl alcohol

Refernces

Modulating charge transfer through cyclic D,L-α-peptide self-assembly

10.1002/chem.200400923

The study focuses on modulating charge transfer through the self-assembly of cyclic d,l-α-peptides, which are organic tubular supramolecular structures with potential applications in molecular electronics. The researchers aimed to control and direct the stacking of aromatic side chains, specifically naphthalenediimide (NDI) derivatives, known for their conductive properties, by using cyclic peptide self-assembly. The purpose of this was to engineer conductive materials with tunable electronic properties. Key chemicals used in the study include NDI-modified cyclic d,l-α-peptides, which were synthesized and characterized for their structural and photoluminescence properties. The efficiency of charge transfer in the resulting supramolecular assemblies was found to depend on the length of the linker between the NDI and the peptide backbone, the distal NDI substituent, and the number of NDIs incorporated in a given structure. The study employed various synthetic routes and analytical techniques such as NMR, fluorescence measurements, and HPLC to probe the self-assembly and charge transfer properties of these peptides.

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