Ossila 2,5-Dibromo-3,4-dinitrothiophene B1351

2,5-Dibromo-3,4-dinitrothiophene (CAS 52431-30-8) is a fully substituted thiophene building block for synthesising organic semiconductor materials. It carries two electron-withdrawing nitro groups at the 3- and 4-positions and two bromine atoms at the 2- and 5-positions, supplied as a white to off-white powder with >98% purity by 1H NMR.

The nitro groups can be reduced to amines, opening a route to electron-deficient thienopyrazines and thieno[3,4-b]thiadiazoles. The bromine end groups make the molecule ready for C-C bond-forming reactions such as Stille and Suzuki couplings, so it can be built into low band gap polymers and small molecules for organic photovoltaics, OLEDs and OFETs.

Reported examples include DPTP-4D, a 2,3-diphenylthieno[3,4-b]pyrazine hole-transporting material with tetrakis-triphenylamino donors, which can replace Spiro-OMeTAD and PTAA and reached a PCE of 20.18% in n-i-p planar perovskite solar cells with good environmental, thermal and light-soaking stability. Thieno[3,4-b]thiadiazole small molecule photodetectors derived from this compound reached a detectivity of 5.0 × 10^11 Jones at 800 nm at -0.1 V bias, and visibly transparent devices with 45% average visible transmittance were made using a thin silver electrode.

• Precursor for electron-deficient thienopyrazines and thieno[3,4-b]thiadiazoles via reduction of the nitro groups.
• Monomer for Stille or Suzuki coupling in the synthesis of low band gap conjugated polymers.
• Synthesis of hole-transporting materials such as DPTP-4D for perovskite solar cells.
• Preparation of small molecule photodetectors, including visibly transparent devices.
• Building block for OLED, OFET and organic photovoltaic materials.

• Product code: B1351
• M​olecular Weight: 331.93 g/mol
• Synonyms: 2,5-Dibromo-3,4-dinitro-thiophene
• Melting Point: 137 °C
• Classification / Family: Thiophene derivatives, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

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