2,3-Bis(4-bromophenyl)fumaronitrile

CAS Number 82193-93-9

Chemistry Building Blocks, COF Ligands, Dibromo Monomers, Materials, Monomers, Porous Organic Frameworks

2,3-Bis(4-bromophenyl)fumaronitrile MSDS

2,3-Bis(4-bromophenyl)fumaronitrile CAS 82193-93-9

Covalent Organic Frameworks (COFs) Fumaronitrile Ligand

A dibromo bridging ligand linker for COFs in application of OLEDs and small molecule organic solar cells (SMOSCs)

Overview
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2,3-Bis(4-bromophenyl)fumaronitrile, CAS number 82193-93-9, belongs to the fumaronitrile family with two 4-bromophenyls replacing the hydrogens on the double bond.

2,3-Bis(4-bromophenyl)fumaronitrile and 4-(carbazol-9-yl)phenylboronic acid via C-C coupling reaction gave stimuli-responsive fluorophoric molecule 2,3-bis[4'-(9-carbazolyl)-(1,1'-biphenyl)-4-yl]-2-butenedinitrile. The molecule demonstrated emission colour switching between green and orange in the solid state upon grinding, heating, and exposure to chemical vapor. NIR fluorescent compound 2,3-bis(4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)fumaronitrile (TPATCN) with a fumaronitrile component, showed a relatively large dipole moment of the charge transfer state. Device based on TPATCN exhibited strong NIR fluorescence with thin film quantum efficiency of 33% and crystal efficiency of 72%. An external quantum efficiency of 2.58% was recorded for non-doped NIR organic light-emitting diode (OLED) device based on TPATCN.

Organic π-conjugated semiconducting chromophore, RCNR, based on alkylated bithiophene terminated fumaronitrile-core acceptor, showed a broad absorption peak near green region and strong emission peak in red due to the strong electron-withdrawing nature of two nitrile (–CN) groups. Fabricated SMOSC devices with RCNR:PC60BM (1:3, w/w) active layer exhibited a power conversion efficiency of 2.69%.

MOF and COF ligands

nitrile and bromide ligand for cross-linked COF/MOF networks

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

Duo functionality

Enabling post-functionalisation

General Information

CAS Number	82193-93-9
Chemical Formula	C₁₆H₈Br₂N₂
Full Name	2,3-Bis(4-bromophenyl)fumaronitrile
Molecular Weight	388.06 g/mol
Synonyms	BPBN, 2,3-Bis(4-bromophenyl)-2-butenedinitrile, (E)-2,3-bis(4-bromophenyl)but-2-enedinitrile
Classification / Family	Fumaronitrile, COF ligands, OLEDs, SMOSCs

Chemical Structure

Product Details

Purity	>98%
Melting Point	216 – 217 °C
Appearance	Off-white powder/crystals

MSDS Documentation

2,3-Bis(4-bromophenyl)fumaronitrile MSDS Sheet

Literature and Reviews

Modulating Photo- and Electroluminescence in a Stimuli-Responsive π-Conjugated Donor–Acceptor Molecular System, K. Isayama et al., Angew. Chem., 130 (37), 12158-12162 (2018); DOI: 10.1002/ange.201806863.
Effective D-A-D type chromophore of fumaronitrile-core and terminal alkylated bithiophene for solution-processed small molecule organic solar cells, M. Nazim et al., Sci. Rep., 5, 11143 (2015); DOI: 10.1038/srep11143.
Non-doped long-wave red electroluminescence for fumaronitrile with fluorenyl or biphenyl group, W. Zhang et al., Opt. Mater., 108, 220425 (2020); DOI: 10.1016/j.optmat.2020.110425.
Preparation of Cyano-Substituted Tetraphenylethylene Derivatives and Their Applications in Solution-Processable OLEDs, X. Sun et al., Molecules, 23(1), 190 (2018); DOI: 10.3390/molecules23010190.
Highly Efficient Solid-State Near-Infrared Emitting Material Based on Triphenylamine and Diphenylfumaronitrile with an EQE of 2.58% in Nondoped Organic Light-Emitting Diode, X. Han et al., Adv. Funct. Mater., 25 (48), 7521-7529 (2015); DOI: 10.1002/adfm.201503344.

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