82193-93-9

Usage

Uses

Used in Organic Synthesis:
2,3-bis(4-bromophenyl)fumaronitrile is utilized as a key intermediate in the synthesis of organic compounds, serving as a fundamental component that can be further processed or modified to create a range of different materials.
Used in Organic Electronics:
In the field of organic electronics, 2,3-bis(4-bromophenyl)fumaronitrile is employed as a precursor for the development of electronic materials, potentially contributing to the advancement of devices such as organic light-emitting diodes (OLEDs), photovoltaic cells, and other electronic components.
Used in Materials Science:
2,3-bis(4-bromophenyl)fumaronitrile is also used as a building block in materials science, where it can be incorporated into the design and synthesis of new materials with specific properties, such as improved conductivity, stability, or other characteristics relevant to various applications.
It is crucial to handle 2,3-bis(4-bromophenyl)fumaronitrile with care due to its potential health and environmental risks, ensuring proper management and disposal to mitigate any adverse effects.

Upstream product

• 859962-02-0 2,3-bis-(4-bromo-phenyl)-2-nitro-succinonitrile 
• 7664-93-9 sulfuric acid 
• 82193-91-7 2,5-Dibromo-3,6-bis-(4-bromo-phenyl)-[1,4]dithiine 1,1,4,4-tetraoxide 
• 16532-79-9 4-Bromophenylacetonitrile 

Downstream Products

• 7664-41-7 ammonia 
• 101422-55-3 3,4-bis(4-bromophenyl)-1H-pyrrole-2,5-dione 
• 638222-73-8 bis{4-[N-(1-naphthyl)phenylamino]phenyl}fumaronitrile 
• 1221894-35-4 2,3-bis(4-(2-(4-(diphenylamino)phenyl)ethynyl)phenyl)fumaronitrile 
• 1221894-36-5 2,3-bis(4-(2-(4-(3,6-ditert-butyl-9H-carbazol-9-yl)phenyl)ethynyl)phenyl)fumaronitrile 
• 1221894-34-3 2,3-bis(4-(diphenylamino)phenyl)fumaronitrile 
• 1221894-33-2 2,3-bis(4-(2-phenyl-1H-indol-1-yl)phenyl)fumaronitrile 
• 1221894-32-1 2,3-bis(4-(1H-indol-1-yl)phenyl)fumaronitrile 

Relevant academic research and scientific papers

Facile Synthesis of Efficient Luminogens with AIE Features for Three-Photon Fluorescence Imaging of the Brain through the Intact Skull

Visualization of the brain in its native environment is important for understanding common brain diseases. Herein, bright luminogens with remarkable aggregation-induced emission (AIE) characteristics and high quantum yields of up to 42.6% in the solid state are synthesized through facile reaction routes. The synthesized molecule, namely BTF, shows ultrabright far-red/near-infrared emission and can be fabricated into AIE dots by a simple nanoprecipitation procedure. Due to their high brightness, large Stokes shift, good biocompatibility, satisfactory photostability, and large three-photon absorption cross section, the AIE dots can be utilized as efficient fluorescent nanoprobes for in vivo brain vascular imaging through the intact skull by a three-photon fluorescence microscopy imaging technique. This is the first example of using AIE dots for the visualization of the cerebral stroke process through the intact skull of a mouse with high penetration depth and good image contrast. Such good results are anticipated to open up a new venue in the development of efficient emitters with strong nonlinear optical effects for noninvasive bioimaging of living brain.

Synthesis and characterization of new helically chiral heptacyclic systems

New helically chiral heptacyclic systems with cyano groups at selected positions have been synthesized in good yields, via a four-step sequence, from readily available materials. The optical properties of the target helicenes were investigated by UV-visible absorption and photoluminescence spectroscopy and an emission in the visible region was observed. The energy levels of these organic materials were determined by cyclic voltammetry and showed a relatively high electronic affinity, indicating that they may be good candidates for electron-injection hole blocking layer in organic light-emitting diodes.

Highly efficient solid-state emission of diphenylfumaronitriles with full-color AIE, and application in explosive sensing, data storage and WLEDs

Luminescent materials with aggregation-induced emission (AIE) have attracted extensive attentions for their strong emission in aggregated states. Although all kinds of AIE luminogens have been recently developed, it is difficult to realize full-color AIE which is popular for the various applications in optoelectronic fields. Herein, a class of diphenylfumaronitrile core-based dyes emitting in a wide region from near ultraviolet (382 nm) to near-infrared (682 nm) have been synthesized and well characterized. It is found that the emission wavelength of the dyes severely depends on the peripheral substituent, including electron-withdrawing trifluoromethyl (1), methyl (2), electron-pushing methoxyl (3), and bulky aromatic amine (7–9), and that the substituting location imposes great effect on the emission intensity of multiple-substituted dyes (4–6). Compound 4 with two methyl substituting at 3,4-position gives a ultrahigh quantum yield of 93percent for unique packing structure. 1–3 and 7 can be used in explosive detecting and data storage for their emission sensitive to picric acid and external stimuli, respectively. When 4 and 8 applied in white-light-emitting diodes (WLEDs), a pure white emission can be obtained with 90 of CRI and (0.32, 0.32) of CIE.

D-A-D type dinitriles with vapor-dependent luminescence in the solid state

D-A-D (Donor-Acceptor-Donor) type dinitriles linked by a styryl or phenylethynyl group have been prepared. These groups were introduced to increase the flexibility and the size of the π-conjugation in the chromophores. Both compounds showed strong emission in the solid state, AIE (aggregation-induced emission) behavior, and mechanochromism. The fluorescence color of ground powder changed by organic solvent vapor (vapochromism). Especially, the emission color of the styryl dinitrile after exposures depends on the solvent, while that of the phenylethynyl dinitrile is the same after exposure to different solvents. These results were explained by single crystal and powder XRD measurements, which revealed that the flexible styryl linker leads to a loose crystal packing, resulting in a dinitrile with multi-state microcrystalline structures. This methodology based on the flexible linker allows for the detection of small organic molecules without transition metals.

An efficient near infrared fluorescent material and biological applications thereof

Efficient near infrared fluorescent dye having a large Stokes shift and applications thereof in the fields of biological imaging and fluorescent labeling, and other fields are disclosed, and belong to the technical field of organic fluorescent dye and applications. The fluorescent dye adopts fumaronitrile as a basic receptor structure unit in the molecular structure. A donor unit having an electron-releasing ability is connected in a conjugated manner to one side through a double bond or connected in a conjugated manner to two sides through double bonds. The structure formula of the fluorescent dye is shown as follows. The fluorescent dye is novel near infrared fluorescent dye synthesized through a Heck reaction, wherein R represents a donor group. Research finds that the dye emits bright near infrared fluorescence under ultraviolet excitation, and the dye has good photobleaching resistance and a high solid quantum efficiency. The dye has the large Stokes shift, and therefore the dye can be used as a near infrared fluorescent material for the fields of biological imaging and fluorescent labeling, and other fields.

Enhanced performance in bulk heterojunction polymer solar cell using water soluble conjugated polymer

We have synthesized water-soluble polymer, poly[(9,9-bis((6a?2-(N,N,N-trimethylammonium) hexyl)-2,7-fluorene))-alt-bisphenylfumaronitrile]dibromide (AHF-alt-PFN), the polymer typically obtained by the Suzuki type of polymerization reaction and shows good solubility in methanol. Bulk heterojunction polymer solar cells (BHJ-PSCs) fabricated by using water soluble conjugated polymer and positive (Cs+) and negative (F-, CO2-3) charge ions doping as an interfacial layer for poly(3-hexylthiophene):phenyl-C61 butyric acid methyl ester (P3HT: PCBM). We have achieved an enhancement of the short circuit density and power conversion efficiency in solar cell by introducing poly(AHF-alt-PFN) layer between the active layer and the cathode metal. The device with poly(AHF-alt-PRN) layer containing F-, CO23- showed a short circuit current density more 1.3, 2.3 times higher than those of the device without poly (AHF-alt-PFN) + ion layer. We explain the better performance in solar cell with poly (AHF-alt-PFN) + ion layer was due not only to the increase of electron mobility in poly (AHF-alt-PFN) layer but also to the decrease of the electron barrier near cathode by the addition of the negative ions.

ORGANIC LIGHT COMPOUND AND ORGANIC LIGHT DEVICE USING THE SAME

PURPOSE: An organic light device is provided to have high luminescent brightness, high luminous efficiency, high color purity, and remarkably improved luminescence lifetime. CONSTITUTION: An organic light device includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. The organic layer includes an organic light emitting compound represented by chemical formula F where E is o or a functional group represented by chemical formula F-a, F-b, or F-c; and each of R1, R2, and R3 is selected from a C5-40 aryl group, C3-40 heteroaryl group, a C5-40 aryloxy group, a C5-40 arylamino group, a C5-40 diarylamino group, a C6-40 arylalkyl group, a C3-40 cycloalkyl group, and a C3-40 heterocycloalkyl group or is group which can form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring together with a neighboring group.

Synthesis and characterization of a novel ambipolar polymer semiconductor based on a fumaronitrile core as an electron-withdrawing group

Two conjugated polymers containing stilbene and fumaronitrile moieties were synthesized to investigate their electronic properties by the existence of electron-withdrawing cyano groups on a vinylene backbone. The cyclic voltammetry investigation and time-dependent density functional theory calculations indicated that the cyano substituents lowered the lowest unoccupied molecular orbital (LUMO) energy level by about 0.65 and 0.63 eV, respectively. The lowering of the LUMO energy levels due to the electron-withdrawing properties of the cyano substituents could enhance electron injection capability. Furthermore, bithiophene-fumaronitrile (donor-acceptor) intermolecular interaction facilitates the self-assembly of the polymer chains. Organic field-effect transistors (OFETs) based on PBTSB without the electron-withdrawing group only exhibit hole transport, while OFETs based on PBTFN with cyano substituents exhibit ambipolar characteristics. The growth of PBTFN crystalline fibrils was observed with increasing annealing temperature, which enhanced hole and electron mobility. A complementary-like inverter using PBTFN with ambipolar properties exhibited good symmetry with an inverting voltage nearly half that of the power supply with a gain of 9 at VDD = 100 V. 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013. Copyright

Red non-doped electroluminescent dyes based on arylamino fumaronitrile derivatives

A diarylamine, 2-(phenylamino)-9,9-diethylfluorene and three red fluorescent dyes based on arylamino fumaronitrile derivatives, bis(4-(N-(1-naphthyl)phenylamino)-phenyl)fumaronitrile (1-NPAFN, 5a), bis(4-(N-(2-naphthyl)phenylamino)phenyl)-fumaronitrile (2-NPAFN, 5b) and bis(4-(N-(9,9-diethyl-2-fluorenyl)phenylamino)-phenyl)fumaronitrile (EFPAFN, 5c), were prepared. The red dyes showed strong red photoluminescence upon excitation which centered at around 635, 650, 658?nm for 1-NPAFN, 2-NPAFN and EFPAFN in solid film respectively. Fluorescence concentration quenching of red dyes was suppressed. Thermal stability and energy levels were also measured. Multilayer non-doped electroluminescent devices were fabricated using the red dyes (5b, 5c) as red emitters. Device performance kept relatively constant at a wide current density level in the range of 20-150?mA/cm2.

Aromatic fumaronitrile core-based donor-linker-acceptor-linker-donor (D-π-A-π-D) compounds: Synthesis and hotophysical properties

A new class of aromatic fumaronitrile core-based compounds with different donors and linkers has been synthesized and well characterized. Compounds 1 and 2 have indole and 2-phenylindole groups as electron donors, respectively. Compounds 3 and 4 have a diphenylamino group as the electron donor, and compound 5 has a 3,6-di-tert-butylcarbazole group as an electron donor. These compounds absorb in the blue-to-green region and emit in the blue-to-red region depending on the electron donor, linker, and solvents. The quantum yields of fluorescence of these compounds in solution are measured and found to be moderate, but in solid states, they are high. These compounds display strong emission solvatochromism that is reflected by a large shift in their fluorescence emission maxima on changing the solvents. This change is accompanied by a successive decrease in fluorescence intensity. The fluorescence lifetimes of these compounds are measured in different solvent and found to vary from 1 to 7 ns. Optical switching of these compounds with solvents, concentration, and excitation energy have been studied. The correlation between the functional group and optical properties has been established to some extent. The ability of these compounds to function as colorimetric and luminescence pH sensors is demonstrated with color changes and luminescence switching upon the addition of trifluoroacetic acid. The potentiality of these compounds for application in optoelectronics has been optically assessed.