5690-24-4

Usage

Uses

Used in Dye and Ink Industry:
1,4,5,8-Naphthalenetetracarboxdiimide is used as a blue pigment for its coloration properties in the production of dyes and inks. Its vibrant hue and stability contribute to the quality and performance of these products.
Used in Chemical Synthesis:
As a precursor, 1,4,5,8-Naphthalenetetracarboxdiimide is utilized in the creation of other chemicals and materials, playing a crucial role in the synthesis of complex organic molecules.
Used in Organic Semiconductors:
1,4,5,8-Naphthalenetetracarboxdiimide is studied for its potential applications in organic semiconductors, where it could contribute to the development of advanced electronic materials and devices.
Used in Research and Development:
In the scientific community, 1,4,5,8-Naphthalenetetracarboxdiimide is employed as a building block for the synthesis of complex organic molecules, aiding in the discovery and innovation of new chemical compounds with various applications.

InChI:InChI=1/C14H6N2O4/c17-11-5-1-2-6-10-8(14(20)16-12(6)18)4-3-7(9(5)10)13(19)15-11/h1-4H,(H,15,17,19)(H,16,18,20)

Upstream product

• 1825-30-5 1,5-dichloronaphthalene 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 7664-41-7 ammonia 
• 858436-00-7 4,8-dichloro-naphthalene-1,5-dicarboxylic acid 

Downstream Products

• 1246286-32-7 (((1,3,6,8-tetraoxobenzo[lmn][3,8]phenanthroline-2,7(1H,3H,6H,8H)-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate) 
• 34151-51-4 N,N’-bis(4-pyridylmethyl)-1,4,5,8-naphthalenetetra-carboxydiimide 
• 910138-52-2 (R)-2-[7-((R)-1-carboxy-2-tritylsulfanyl-ethyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl]-3-tritylsulfanyl-propionic acid 
• 828301-12-8 [S,S]-N,N'-bis-[4-(benzyloxycarbonyl)-2-(N-5-fluoro-2,4-dinitrophenylamino)-butanoyl]-2,7-diaza-1,2,3,6,7,8-hexahydropyrene 
• 828301-11-7 [S,S]-N,N'-bis-[3-(benzyloxycarbonyl)-2-(N-5-fluoro-2,4-dinitrophenylamino)-propionyl]-2,7-diaza-1,2,3,6,7,8-hexahydropyrene 
• 828301-09-3 [S,S]-N,N'-bis-[4-(benzyloxycarbonyl)-2-(N-t-butoxycarbonylamino)-butanoyl]-2,7-diaza-1,2,3,6,7,8-hexahydropyrene 

Relevant academic research and scientific papers

A facile synthesis of 2,7-diazapyrene

2,7-Diazapyrene is synthesized in three high-yield steps from commercially available 1,4,5,8-naphthalene tetracarboxylic dianhydride, which first reacts with concentrated ammonium hydroxide solution at room temperature to give 1,4,5,8-naphthalenetetracarboxylic diimide (96%). The latter compound is subsequently reduced with borane in refluxing tetrahydrofuran to give 1,2,3,6,7,8-hexahydro-2,7-diazapyrene (77%), which in turn is oxidized with manganese dioxide in refluxing benzene giving 2,7-diazapyrene (71%).

Synthesis and crystal packing structures of 2,7-diazapyrenes with various alkyl groups at 1,3,6,8-positions

We have developed the synthesis of 1,3,6,8-tetramethoxy-2,7-diazapyrene through reductive aromatization of naphthalene diimide. The methoxy groups were readily converted to a variety of alkyl groups through Ni-catalyzed cross-coupling reaction with alkyl Grignard reagents. The peripheral substituents significantly influenced the packing structures of 2,7-diazapyrenes in the solid state.

Molecular Orientation Change in Naphthalene Diimide Thin Films Induced by Removal of Thermally Cleavable Substituents

The potential of naphthalene-1,8:4,5-tetracarboxylic diimide (NDI-H) as a transparent electron-transporting material was examined. A soluble precursor was designed and synthesized having two tert-butoxycarbonyl solubilizing substituents at the imide moieties. This precursor molecule, NDI-Boc, is converted to the hydrogen-substituted NDI-H by heating the spin-coated precursor films. The molecular orientation during the thermal conversion of NDI-Boc to NDI-H was examined using two-dimensional grazing incidence X-ray diffraction (2D-GIXD) and p-polarized multiple-angle incidence resolution spectrometry. It was revealed that, driven by the formation of intermolecular hydrogen bonds, the molecular orientation changes from tilted edge-on to face-on orientation. In situ 2D-GIXD measurements confirmed that the change of molecular orientation is simultaneously caused by the cleaving of the Boc substituents. Time-resolved microwave conductivity measurements were used to show that the resulting NDI-H film has anisotropic charge-carrier transport with preferential mobility in the direction perpendicular to the film plane. We fabricated perovskite solar cells to demonstrate that the NDI-H film effectively functions as the bottom electron-transporting layer in these devices.

Macrocyclization and molecular interlocking via Mitsunobu alkylation: Highlighting the role of C-H...O interactions in templating

(Formula presented) A series of diimide-based macrocycles have been prepared using Mitsunobu-mediated alkylation as the macrocyclization step. These macrocycles could not be incorporated into [2]catenanes using previously established building blocks and coupling methodology. However, when one of the macrocycle syntheses was conducted in the presence of a dinaphtho crown ether, catenane formation was achieved. This result is discussed in terms of the ability of the components to establish intermolecular C-H...O hydrogen-bonding contacts.

The reductive aromatization of naphthalene diimide: A versatile platform for 2,7-diazapyrenes

The reductive aromatization of naphthalene diimide provides tetrapivaloxy-2,7-diazapyrene, which serves as a versatile platform toward peripherally substituted 2,7-diazapyrenes. Time-resolved microwave conductivity measurements demonstrated that the intrinsic electron mobility of 2,7-diazapyrene is significantly higher than that of the corresponding pyrene.

Effects of Zn2+and H+association with naphthalene diimide electrodes for aqueous Zn-ion batteries

Organic electrodes have been extensively developed to enhance cycling performance in aqueous zinc (Zn)-ion cells. However, little is known about an ion-association process, which caused insufficient diagnoses of various cyclability results. Protons (H+) are charge carriers alongside Zn2+ ions in mildly acidic electrolyte solutions and preferentially participate in the storage process. In addition, dissociation of water can supply the additional H+, and the increased pH yields the precipitate of zinc hydroxy sulfate. Here, we demonstrated the critical effect of the H+ for cycling stability of Zn-ion cells, using a 1,4,5,8-naphthalene diimide (NDI) electrode. Stepwise electron transfer of the NDI electrode proceeded via surface association of the charge carriers and subsequent solid-state diffusion. The H+ intercalation to the NDI electrode became pronounced with an increasing current rate and led to the dissolution of the NDI molecules. We exhibited stable 1000 cycles with a capacity retention of 93.8% by suppression of the H+ impact and suggested a solution-mediated NDI reassembly mechanism as the core reason for the capacity fading.

NEW ANTI-CLOSTRIDIUM COMPOUNDS

The present invention relates to compounds having a backbone structure for use as antibiotic, more specifically use against infections with Gram positive bacteria, preferably Clostridium, more preferably C. difficile or C. perfringens. The compounds of the invention are particularly useful against spores of these bacteria.

1. 4, 5, 8 - tetra formyl imide derivatives and use thereof (by machine translation)

The invention relates to a 1, 4, 5, 8 - tetra formyl diimide derivative and its use. The 1, 4, 5, 8 - tetra formyl diimide derivative compound of formula I is shown, it can be regarded as the acidic copper plating of a leveling agent application. In formula I, R1 And R2 Are independently selected from: hydrogen, C1 - C6 Alkyl, halogenated C1 - C6 Alkyl, type II shown in the formula III the group indicated in the group, and R1 And R2 At least one of the shown in formula II or formula III group shown group; m is 1 or 2; X is halogen; Wherein R3 - R8 Are independently selected from the group: C1 - C3 Alkyls, n is 1 - 12 of the integer, p is 1 - 6 of the integer. (by machine translation)

Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions

Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.

Characterization of NTCDI supra-molecular networks on Au(111); Combining STM, IR and DFT calculations

In this paper, we investigate the self-organization of NTCDI molecules on Au(111) surface by combining Density Functional Theory (DFT) and experiments based on scanning tunneling microscopy (STM) and infrared spectroscopy measurements. The competition between the cohesive and adsorption energy on the flat surface is discussed. It was shown that the network is mainly stabilized by cohesive interactions explaining the mobility of the network over the surface. The comparison between experimental and infrared spectra enables confirmation of the effect and importance of the H-bonds in the network stability. STM images at different voltages and in ambient conditions were interpreted by projected density of states calculations and compared with experiment. The theoretically proposed network geometry was characterized at the molecular level reproducing the experimental STM image. the Partner Organisations 2014.