2,3-Bis(4-bromophenyl)fumaronitrile (BPBN, CAS 82193-93-9) is a fumaronitrile building block in which both hydrogens on the central double bond carry a 4-bromophenyl group. Supplied by Ossila at >98% purity as an off-white powder or crystals, it acts as a dibromo bridging linker for covalent organic frameworks (COFs) and as a precursor for OLED and small molecule organic solar cell (SMOSC) materials.
Its two bromide sites allow C-C coupling, while the nitrile groups provide strong electron-withdrawing character and options for post-functionalization in cross-linked COF/MOF networks. Coupling with 4-(carbazol-9-yl)phenylboronic acid has produced a stimuli-responsive fluorophore whose solid-state emission switches between green and orange on grinding, heating or chemical vapor exposure.
Related fumaronitrile-based emitters such as TPATCN gave strong NIR fluorescence (thin film quantum efficiency 33%, crystal 72%) and an external quantum efficiency of 2.58% in a non-doped NIR OLED. A fumaronitrile-core chromophore, RCNR, reached a power conversion efficiency of 2.69% in SMOSC devices with an RCNR:PC60BM (1:3, w/w) active layer.
- Dibromo bridging linker for building covalent organic frameworks (COFs) and MOF networks.
- Precursor for stimuli-responsive fluorophores prepared via C-C coupling reactions.
- Building block for NIR and red emitters used in non-doped OLED devices.
- Acceptor core for donor-acceptor chromophores in small molecule organic solar cells.
| Brand | Ossila |
|---|---|
| CAS number | 82193-93-9 |
| Molecular formula | C16H8Br2N2 |
| Purity | >98% |
| Category | — |
| Pack sizes | 500 mg, 1 g, 5 g |
| Physical form | Off-white powder/crystals |
| Storage | — |
- Product code: B3761
- 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
- Melting Point: 216 – 217 °C
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