2,5-Dibromo-3,4-dinitrothiophene

CAS Number 52431-30-8

Chemistry Building Blocks, Dibromo Monomers, Heterocyclic Building Blocks, Materials, Monomers

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

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

Specifications | MSDS | Literature and Reviews

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.

Dinitrothiophene building block

for the synthesis of OLED and organic photovoltaic materials

Worldwide shipping

Quick and reliable shipping

Capped with bromides

for facile coupling reactions

High purity

>97% Purity

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

Product Details

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

MSDS Documentation

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

Literature and Reviews

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.
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.
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.

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.
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.
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.
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.
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.
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.
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.