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Product Code B1351-5g
Price £130 ex. VAT

A fully functionalised thiophene unit

Used for the synthesis of electron deficient thieno[3,4-b]thiadiazoles or thienopyrazines in application of organic solar cells and photodetectors

2,5-Dibromo-3,4-dinitrothiophene (CAS number 52431-30-8) is a fully substituted thiophene unit with two electron withdrawing nitro groups at 3,4-positions and two bromo functional groups at 2,5-postions. Nitro groups can be reduced to amino groups to further form thienopyrazines and thieno[3,4-b]thiadiazole. Bromo groups gives the functionality for C-C formation reactions, i.e. Stille or Suzuki couplings.

DPTP-4D, a 2,3-diphenylthieno[3,4-b]pyrazine based small molecule containing tetrakis-triphenyl amino donors, could be synthesised from simple, low cost and readily available 2,5-dibromo-3,4-dinitrothiophene. Being an effective hole-transporting material, DPTP-4D can be used to replace Spiro-OMeTAD and PTAA. It gained a PCE of 20.18% with high environmental, thermal, and light-soaking stability in PSC n-i-p planar devices.

Small molecule photodetectors (SMPDs) based on thieno[3,4-b]thiadiazole, also derived from 2,5-dibromo-3,4-dinitrothiophene showed a high detectivity of 5.0 × 1011 Jones at 800 nm at the bias of -0.1 V. With a sufficiently thin silver electrode, visibly transparent PDs with an average transmittance of 45% in the visible region were fabricated.

General Information

CAS Number 52431-30-8
Chemical Formula C4Br2N2O4S
Full Name 2,5-Dibromo-3,4-dinitrothiophene
Molecular Weight 331.93 g/mol
Synonyms 2,5-Dibromo-3,4-dinitro-thiophene
Classification / Family Thiophene derivatives, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

2,5-Dibromo-3,4-dinitrothiophene chemical structure, CAS 52431-30-8
2,5-Dibromo-3,4-dinitrothiophene chemical structure, CAS 52431-30-8

Product Details

Purity >98% (1H NMR)
Melting Point Tm = 137 °C
Appearance White to off-white powder

MSDS Documentation

2,5-Dibromo-3,4-dinitrothiophene2,5-Dibromo-3,4-dinitrothiophene MSDS Sheet

Literature and Reviews

  1. Synthesis of thienoselenadiazole-containing conjugated copolymers and their application in polymer solar cells, X Shen et al., Polym. J, 44, 978–981 (2012): DOI:10.1038/pj.2012.33.
  2. Multicolored Electrochromic Cells Based On Poly(2,7-Carbazole) Derivatives For Adaptive Camouflage, S. Beaupré et al., Chem. Mater., 21, 8, 1504–1513 (2009); DOI: 10.1021/cm802941e.
  3. Synthesis and structural characterization of 2,5-dihalo-3,4-dinitrothiophenes, L. Wen et al., J. Chem. Crystallogr., 37, 387–398 (2007); DOI: 10.1007/s10870-006-9160-y.
  4. Electrogenerated poly(thiophenes) with extremely narrow bandgap and high stability under n-doping cycling, S. Akoudad et al., Chem. Commun., 2081-2082 (1998); DOI: 10.1039/A804992K.
  5. Poly(3,4-dinitrothiophene)/SWCNT composite as a low overpotential hydrogen evolution metal-free catalyst, K. Xieet al., J. Mater. Chem. A, 3, 78-82 (2015); DOI: 10.1039/C4TA04671D.
  6. The effect of changes in π-conjugated terthienyl systems using thienyl and ethylenedioxybenzene functionalized thieno[3,4-b]pyrazine precursors: Multicolored low band gap polymers, S. Tarkuc et al., Electrochim. Acta, 55, 7254–7258 (2010); DOI: 10.1016/j.electacta.2010.07.017.
  7. Ferrocenes Bridged by Ethylenediamino Thiophene: Varying Charge Transfer Properties in a Series of 3,4-Di-N-substituted 2,5-Diferrocenyl Thiophenes, J. Speck et al., Organometallics, 34, 15, 3788–3798 (2015); DOI: 10.1021/acs.organomet.5b00450.
  8. Alternating Donor/Acceptor Repeat Units in Polythiophenes. Intramolecular Charge Transfer for Reducing Band Gaps in Fully Substituted Conjugated Polymers, Q. Zhang et al., J. Am. Chem. Soc., 120, 22, 5355–5362 (1998); DOI: 10.1021/ja972373e.
  9. Synthesis and Spectroscopic Characterization of Thienopyrazine-Based Fluorophores for Application in Luminescent Solar Concentrators (LSCs), X. Yzeiri et al., Molecules, 26(18), 5428 (2021); DOI: 10.3390/molecules26185428.
  10. Design of Narrow-Bandgap Polymers. Syntheses and Properties of Monomers and Polymers Containing Aromatic-Donor and o-Quinoid-Acceptor Units, C. Kitamura et al., Chem. Mater., 8, 2, 570–578 (1996); DOI: 10.1021/cm950467m.
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