72452-47-2

Basic information

• Product Name: 1,3-Bis(3,4-dicyanophenoxy)benzene
• Synonyms: 1,3-Bis(3,4-dicyanophenoxy)benzene
• CAS NO: 72452-47-2
• Molecular Formula: C22H10N4O2
• Molecular Weight: 362.34
• Mol File: 72452-47-2.mol

Chemical Properties

• Melting Point: 185 ºC
• Boiling Point: 614.9 °C at 760 mmHg
• Flash Point: 237 °C
• Appearance: /
• Density: 1.39
• Vapor Pressure: 4.71E-15mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,3-Bis(3,4-dicyanophenoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(3,4-dicyanophenoxy)benzene(72452-47-2)
• EPA Substance Registry System: 1,3-Bis(3,4-dicyanophenoxy)benzene(72452-47-2)

Safety Data

• Hazardous Substances Data: 72452-47-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Light-Emitting Diodes (OLEDs) Industry:
1,3-Bis(3,4-dicyanophenoxy)benzene is used as a key component in the development of organic light-emitting diodes (OLEDs) for its ability to enhance the performance and efficiency of these devices. Its unique molecular structure contributes to improved light emission and color quality in OLED displays.
Used in Electronic Devices Industry:
1,3-Bis(3,4-dicyanophenoxy)benzene is utilized as a material in the fabrication of electronic devices, such as transistors and sensors, due to its electronic properties. Its incorporation into these devices can lead to enhanced performance, stability, and reliability.
Used in Photonic Materials Industry:
1,3-Bis(3,4-dicyanophenoxy)benzene is employed as a constituent in the production of photonic materials, which are essential for various optical applications, including optical communication and sensing systems. Its optical properties make it suitable for the development of materials with tailored light manipulation capabilities.
Used in Advanced Material Development:
1,3-Bis(3,4-dicyanophenoxy)benzene is studied for its potential use in the development of new materials for cutting-edge technological applications. Its unique properties and molecular structure offer opportunities for the creation of innovative materials with improved performance and functionality in various fields.

InChI:InChI=1/C22H10N4O2/c23-11-15-4-6-21(8-17(15)13-25)27-19-2-1-3-20(10-19)28-22-7-5-16(12-24)18(9-22)14-26/h1-10H

Upstream product

• 31643-49-9 4-Nitrophthalonitrile 
• 108-46-3 recorcinol 

Relevant articles and documents

A novel curing agent for phthalonitrile monomers: Curing behaviors and properties of the polymer network

A novel methyl tetrahydrophthalic anhydride end-capped imide compound (MODA) was firstly used to promote the curing reaction of phthalonitrile monomer 1,3-bis(3,4-dicyanophenoxy) (3BOCN). The curing behaviors of 3BOCN/MODA blend were studied by differential scanning calorimetry (DSC) and rheological analysis, which suggested that the blend possessed a wide processing window. IR spectra exhibited no triazine has been formed in the curing process and the nitrile group absorption peak almost disappeared after post-cured, the thermogravimetric analysis (TGA) and dynamic mechanical analysis (DMA) revealed that the cured phthalonitrile resins have excellent thermal properties and high glass transition temperature (Tg).

Systematic study on highly efficient Thermal Synergistic Polymerization effect between alicyclic imide moiety and phthalonitrile: Scope, Properties and Mechanism

Blends of phthalonitrile (CN) and alicyclic imide compounds synthesized from tetrahydrophthalic anhydride (CC), methyl tetrahydrophthalic anhydride (MCC) and hexahydrophthalic anhydride (HCC), respectively, were prepared and characterized. Results from rheological studies demonstrated the scope of a novel Thermal Synergistic Polymerization (TSP) effect between phthalonitrile and the alicyclic imide compounds. FTIR data showed a unique phenomenon, which is, the [sbnd]C[tbnd]N of the phthalonitrile compound could be completely and rapidly consumed without generating any triazine ring. Further works on cured products of CC/CN system showed comparable or even higher thermal oxidation stability, low boiling water absorbance and moderate dielectric constant (ε′ in the range of 4.8～4.5) with almost no voids compared with that of the phthalonitrile resins promoted by traditional curing system of active hydrogen. Model system was designed to study the mechanism of TSP effect of alicyclic imide moiety/phthalonitrile. The systematic characterizations by FTIR, UV–Vis, MALDI-TOF MS, free radical scavenger (DPPH), EPR, etc. showed that the TSP reaction undergoes both copolymerization and homopolymerization with no triazine formation, involving a free radical process. Structural analysis of the oligomers suggested that phthalocyanine rings were a minor component of the thermoset networks, while polyisoindolines were the primary structural motif.

Synthesis, spectroscopic properties and redox behavior kinetics of rare-earth bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato metal complexes with er, lu and yb

Novel bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato of complexes er-bium, lutetium and ytterbium were synthesized using a template fusion method to prevent any polymerization process. The complexes were separated from the reaction mixtures and characterized by NMR, IR and electron absorption spectroscopy. The spectroscopic properties of the metal ph-thalocyaninates in chloroform, acetone and tetrahydrofuran were studied. The regular bathochromic shift in the Er–Yb–Lu series was determined. In acetone medium all the complexes obtained were found to exist in an equilibrium state between neutral and reduced forms. The linearity of Lambert-Bouger-Beer curves makes it possible to study the kinetics of redox processes in the presence of phenylhydrazine and bromine. The lutetium complex showed better reducing properties and turned fully into the reduced form, while the erbium and ytterbium ones changed only partially. Upon oxidizing all the phthalocyaninates transformed into a mixture of oxidized and neutral-radical forms. The extinction coefficients and effective redox constants were calculated.

Non-aggregated hyperbranched phthalocyanines: Single molecular nanostructures for efficient semi-opaque photovoltaics

A series of single molecular nanostructured hyperbranched phthalocyanines, HBMPc-COOH (M = H2, AlCl, Co, Cu, Zn), have been synthesized, characterized, and systematically studied as efficient semi-opaque sensitizers of TiO2 by using ultraviolet-visible absorption, steady-state and femtosecond time-resolved fluorescence, cyclic voltammetry, current-voltage and photoelectric measurements. The inherent steric effect within these hyperbranched structures effectively suppresses the aggregation of phthalocyanine rings on TiO2 surface, providing a facile approach for improving the photovoltaic performance of phthalocyanine-based dye sensitized solar cells (DSSCs). A power conversion efficiency of 1.15% along with a high incident photon to current conversion efficiency of 66.7% at 670 nm is achieved from HBZnPc-COOH sensitized solar cells. These results are consistent with findings from the femtosecond time-resolved fluorescence study, which reveals an ultrafast and efficient multi-phasic interfacial electron injection from both the Soret and Q bands to the conduction band of TiO2. The changing of the metal centers dramatically affects the optical, photophysical, electrochemical, and photovoltaic properties of the hyperbranched phthalocyanines. Zinc has been found to be the best metal center in the whole series for the design of hyperbranched phthalocyanine-based dyes for DSSC applications.

Photo-physico-chemical properties of 1,3-benzenediol-substituted face-to-face phthalocyanines

Here, we report the synthesis of new ball-type phthalocyanines that are symmetrically substituted with Mg–Mg, Zn–Zn, and Co–Co centers and contain four 1, 3-benzenediol substituents at the beta positions. The structures and photophysical properties, including the fluorescence quantum yield, triplet quantum yield, and photochemical properties with singlet oxygen quantum yield, of these compounds were investigated. Moreover, the applicability of these molecules as photosynthesizers in cancer nanomedicines is discussed. Furthermore, the photodegradation quantum yield of the complexes with the inclusion of Co binuclear phthalocyanine was examined, and their fluorescence and triplet lifetimes were studied in dimethyl sulfoxide. The obtained Uv–Vis spectra exhibited unexpected results; for instance, H2Pc exhibited a broad and peculiar Q band with D4h symmetry. Moreover, H2Pc was found to have a triplet lifetime of 460 μs whereas ZnPc had a higher triplet lifetime of 1100 μs.

Synthesis, catalytic, spectroscopic, fluorescent and coordination properties of dicyanophenoxy-substituted phthalocyaninates of d-metals

Isomeric phthalonitriles having four terminal cyano-groups are synthesized by means of nucleophilic replacement of 4-nitrophthalonitrile's nitro-group with resorcinol and hydroquinone fragments. Corresponding phthalocyaninates of cobalt, zinc, nickel and

Synthesis and spectral properties of isomers of cobalt tetrakis(dicyanophenoxy)phthalocyaninate

4,4′-[1,3-Phenylenebis(oxy)]- and 4,4′-(1,4-phenylenebis(oxy)]diphthalonitriles and the corresponding tetrasubstituted cobalt phthalocyaninates were synthesized. The spectral properties of the synthesized complexes in various organic solvents were studied

BISPHENOL M DIPHTHALONITRILE ETHER RESIN, BISPHENOL P DIPHTHALONITRILE ETHER RESIN, METHODS OF MAKING SAME, RESIN BLENDS, AND TWO COMPONENT SYSTEMS

Resins are provided including bisphenol M diphthalonitrile ether resin or bisphenol P diphthalonitrile either resin. Compositions are also provided, including a primary amine curative and the bisphenol M diphthalonitrile ether resin or the bisphenol P diphthalonitrile either resin. Further, polymerized products are provided of the bisphenol M diphthalonitrile ether resin or the bisphenol P diphthalonitrile either resin. In addition, a method of making a polymerized network is provided. A two component system is further provided, including a curative in one of the components and the bisphenol M diphthalonitrile ether resin or the bisphenol P diphthalonitrile either resin in the other component. In addition, a resin blend is provided, including a blend of at least two of bisphenol M diphthalonitrile ether resin, bisphenol P diphthalonitrile either resin, or bisphenol T diphthalonitrile ether resin.

Phthalonitrile compound

The present invention relates to a phthalonitrile compound represented by chemical formula 1 and a phthalonitrile resin obtained therefrom, a polymerizable composition, a prepolymer, a complex and a method for manufacturing the complex. The phthalonitrile

Preparation of self-promoted hydroxy-containing phthalonitrile resins by an in situ reaction

The in situ reaction of a hydroxy group with a phthalonitrile system was carried out by the simple nucleophilic displacement of a nitro-substituent from 4-nitrophthalonitrile in a dipolar aprotic solvent, in a one-pot reaction. The hydroxy-containing phth