1239327-73-1

Basic information

• Product Name: 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
• Synonyms: 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone;N,N'-Dihexyl-2,6-dibromonaphthalene-1,4,5,8-tetracarboxydianhydride;9-DibroMo-2,7-dihexylbenzo[lMn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone;4,9-DibroMo-2,7-dihexylbenzo[lMn][3,8]phenanthroline-1,3,6,8-tetraone;4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• CAS NO: 1239327-73-1
• Molecular Formula: C₂₆H₂₈Br₂N₂O₄
• Molecular Weight: 592.31952
• Mol File: 1239327-73-1.mol

Chemical Properties

• Appearance: /
• Density: 1.521
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone(CAS DataBase Reference)
• NIST Chemistry Reference: 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone(1239327-73-1)
• EPA Substance Registry System: 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone(1239327-73-1)

Safety Data

• Hazardous Substances Data: 1239327-73-1(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone is used as a potential antiviral and anticancer agent due to the known properties of tetrone compounds. Its bromine content may enhance its reactivity and interaction with biological targets, contributing to its therapeutic potential.
Used in Organic Synthesis:
In the field of organic synthesis, 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone is used as a building block or intermediate for the creation of more complex molecules. Its unique structure, including the bromine and hexyl groups, allows for specific reactions and modifications that can be exploited in the synthesis of novel compounds with various applications.
Used in Drug Development:
4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone is used as a lead compound in drug development for its potential to target and treat viral infections and cancer. 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone's hydrophobic properties, due to the hexyl groups, may facilitate interactions with lipid membranes, which is important for the transport and delivery of drugs.
Used in Chemical Research:
In the realm of chemical research, 4,9-Dibromo-2,7-dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone serves as a subject for studying the effects of bromine and hexyl substituents on the compound's reactivity, stability, and biological activity. Understanding these effects can inform the design of new molecules with improved or novel properties.

Upstream product

• 111-26-2 hexan-1-amine 
• 83204-68-6 2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 

Downstream Products

• 1397707-90-2 C₃₈H₅₂N₄O₄ 

Relevant articles and documents

Naphthalenediimide bridged D-A polymers: Design, synthesis and electrochromic properties Dedicated to Professor Eyup Ozdemir.

We have synthesized two new D-A electrochromic polymers; poly(N,N'-bis(2-hexyl)-2,6-dithiophene-1,4,5,8-naphthalenediimide) (PTNDI) and poly(N,N'-bis(2-hexyl)-2,6-(3,4-ethylenedioxythiophene)-1,4,5, 8-naphthalenedimiide) (PENDI) bearing a naphthalenedimiide chromophore in the backbone. Structural characterization of initial compounds and products were carried out by using FT-IR and 1H-NMR spectroscopies. The optical and electrochemical properties of these polymers were investigated by UV-Vis absorption spectroscopy and cyclic voltammetry, respectively. The results of spectroelectrochemical studies indicate that both polymers reveal various colors due to ambipolar redox behavior at cathodic and anodic regime. Both polymer films have reasonable redox stability (in the range of 75-80% after 1000 cycles), coloration efficiency (in the range of 80-100 cm2 C -1), and response time (approx. 1s). Moreover, it is clearly seen that replacing donor unit from thiophene to EDOT results in change only in neutral state color.

Unexpected photoluminescence of fluorinated naphthalene diimides

Two new amino core-substituted naphthalene diimides (cNDIs) bearing fluorinated side chains have been synthesised. Steady-state and time-resolved fluorescence spectroscopy reveals unprecedented optical properties for the cNDIs with high quantum yields of ~0.8 and fluorescence lifetimes of ~13 ns in a range of solvents. These properties are apparent at the level of single molecules, where the compounds also show exceptional photostability under pulsed-laser excitation. Photon emission is remarkably consistent with very few long timescale (millisecond or longer) interruptions with molecules regularly undergoing >107 cycles of excitation and emission. Intermittencies owing to triplet-state formation occur on a sub-millisecond timescale with a low yield of 1-2%, indicating that the presence of the fluorine atoms does not lead to a significant triplet yield through the heavy-atom effect. These properties make the compounds excellent candidates for single-molecule labelling applications.

Organic small molecule electron transport material based on naphthalimide unit and application thereof

The invention provides an organic small molecule electron transport material based on a naphthalimide unit and application thereof, belongs to the field of organic photoelectric materials, and solves the problems that in the prior art, the quantum dot light-emitting diode device is few in electron transport material selection and poor in device stability. The chemical structure of the organic small molecule electron transport material contains a naphthalimide unit, and the organic small molecule electron transport material has the advantages that 1) the lowest unoccupied molecular orbital energy level is low, electron injection and transport in a QLED device are facilitated, the highest occupied molecular orbital energy level is low, hole injection in the QLED device can be blocked, and the above two aspects are beneficial for improving the electroluminescent efficiency of the QLED device; (2) the absorption spectrum is mainly not located in a visible light region and does not absorb light emitted by the light-emitting layer in the QLED device; and 3) the material has a rigid configuration, can inhibit crystallization of the material, is beneficial to processing in a QLED, and is beneficial to improving the stability of a QLED device.

Halogen-Bonded Assemblies of Arylene Imides and Diimides: Insight from Electronic, Structural, and Computational Studies

Halogen-bonding interactions in electron-deficient π scaffolds have largely been underexplored. Herein, the halogen-bonding properties of arylene imide/diimide-based electron-deficient scaffolds were studied. The influence of scaffold size, from small (phthalimide) to moderately sized (pyromellitic diimide or naphthalenediimides) to large (perylenediimide), axial-group modification, and number of halo substituents on the halogen bonding and its self-assembly was probed in a set of nine compounds. The structural modification leads to tunable optical and redox properties. The first reduction potential (Formula presented.) ranges between ?1.09 and ?0.17 V (vs. SCE). Two of the compounds, that is, 6 and 9, have deep-lying LUMOs with values reaching ?4.2 eV. Single crystals of all nine systems were obtained, which showed Br???O, Br???Br, or Br???π halogen-bonding interactions, and a few systems are capable of forming all three types. These interactions lead to halogen-bonded rings (up to 12-membered), which propagate to form stacked 1D, 2D, or corrugated sheets. A few outliers were also identified, for example, molecules that prefer C?H???O hydrogen bonding over halogen bonding, or noncentrosymmetric rather than centrosymmetric organization. Computational studies based on Atoms in Molecules and Natural Bond Orbital analysis provided further insight into the halogen-bonding interactions. This study can lead to a predictive design tool-box to further explore related systems on surfaces reinforced by these weak directional forces.

Core-fluorinated naphthalene diimides: Synthesis, characterization, and application in n-type organic field-effect transistors

A series of difluoro- and tetrafluoro-substituted naphthalene diimides (NDIs) were synthesized by halogen exchange reactions of corresponding bromo-NDIs with CsF in dioxane. Two strong electron acceptor molecules 6 and 8 with low-lying LUMO energy levels of -4.27 and -4.54 eV were obtained, starting from tetrafluoro-NDI. Organic field-effect transistors (OFETs) based on these fluorinated NDIs were fabricated by vapor deposition, exhibiting n-channel field-effect character under ambient conditions with the highest mobility of 0.1 cm2 V-1 s-1.

Naphthalene diimide based materials with adjustable redox potentials: Evaluation for organic lithium-ion batteries

The promising crystallinity and tunable redox capabilities of naphthalene diimides make them attractive candidates as electroactive materials for organic-based lithium-ion batteries. In this study, a family of naphthalene diimide derivates was synthesized and their redox properties explored with the intent of unveiling structures with reduction potentials that are higher than those encountered in previous organic redox processes. Changes in the electronic characteristics of the aryl substituents resulted in materials with discharge potentials that vary from 2.3 to 2.9 V vs Li/Li+, with discharge capacities as high as 121 mAh/g.

Naphthalenediimide bridged D-A polymers: Design, synthesis and electrochromic properties Dedicated to Professor Eyup Ozdemir.

We have synthesized two new D-A electrochromic polymers; poly(N,N'-bis(2-hexyl)-2,6-dithiophene-1,4,5,8-naphthalenediimide) (PTNDI) and poly(N,N'-bis(2-hexyl)-2,6-(3,4-ethylenedioxythiophene)-1,4,5,8-naphthalenedimiide) (PENDI) bearing a naphthalenedimiide chromophore in the backbone. Structural characterization of initial compounds and products were carried out by using FT-IR and 1H-NMR spectroscopies. The optical and electrochemical properties of these polymers were investigated by UV-Vis absorption spectroscopy and cyclic voltammetry, respectively. The results of spectroelectrochemical studies indicate that both polymers reveal various colors due to ambipolar redox behavior at cathodic and anodic regime. Both polymer films have reasonable redox stability (in the range of 75-80% after 1000 cycles), coloration efficiency (in the range of 80-100 cm2 C-1), and response time (approx. 1s). Moreover, it is clearly seen that replacing donor unit from thiophene to EDOT results in change only in neutral state color.

REACTION PRODUCTS OF STANNYL DERIVATIVES OF NAPHTHALENE DIIMIDES WITH RYLENE COMPOUNDS

NDI-tin compounds are reacted with rylene compounds to form NDI-rylene compounds. The rylene compounds can be perylene compounds. The NDI-rylene compounds can be used in organic electronic devices including in a field-effect transistor.