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2,3-Bis(4-bromophenyl)fumaronitrile

CAS Number 82193-93-9

Chemistry Building Blocks, COF Ligands, Dibromo Monomers, Materials, Monomers


Product Code B3761-500mg
Price $188 ex. VAT

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Covalent Organic Frameworks (COFs) Fumaronitrile Ligand

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


2,3-Bis(4-bromophenyl)fumaronitrile 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

MOF and COF ligands

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

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High purity 82193-93-9

High purity

>98% High purity

Duo functionality

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

82193-93-9 - 2,3-bis(4-bromophenyl)fumaronitrile chemical structure
2,3-Bis(4-bromophenyl)fumaronitrile (BPBN) Chemical Structure, 82193-93-9

Product Details

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

MSDS Documentation

82193-93-9 - 2,3-bis(4-bromophenyl)fumaronitrile2,3-Bis(4-bromophenyl)fumaronitrile MSDS Sheet

Literature and Reviews

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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