2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene

CAS Number 67061-69-2

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

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene MSDS

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene CAS 67061-69-2

High-quality 2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene

Widely used as intermediate for semiconducting molecules, oligomers, and conjugated polymer synthesis for the applications of OFETs and OPVs.

Specifications | MSDS | Literature and Reviews

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene (2,6-Dibromo-DTT, CAS number 67061-69-2) is a bis-brominated derivates of thieno[3,2-b:2′,3′-d]thiophene (DTT), which have unique electronic properties due to its planar, conjugated, sulfur-rich, and highly thermally stable structure, contains three annulated thiophene rings and is one of the six isomers of DTTs. DTTs having planar and rigid structures show intense electronic absorption, good hole mobility and high stability. In particular, being closely packed, rigid and planar structures lead to better charge injection efficiency in solid state.

The synthesis of 2,6-bis(dicyanomethylene)-2,6-dihydrodithieno[3,2-b:2',3'-d]thiophene

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene is synthesised by reacting thieno[3,2-b:2′,3′-d]thiophene with N-Bromosuccinimide in dimethylformamide (DMF).Treatment of 2,6-dibromodithieno(3,2-b:2',3'-d]thiophene with tetracyanoethylene oxide in 1,2-dibromoethane under reflux gives 2,6-bis(dicyanomethylene)-2,6-dihydrodithieno[3,2-b:2',3'-d]thiophene as violet deep fine crystals.

Solar cell based on polymer semiconductor 2,6-di(pyren-1-yl) dithieno[3,2-b:2',3'-d]thiophene (DDT), consisting of dithieno [3,2-b:2',3'-d]thiophene (DTT) and pyrene units, as donor and C70 as acceptor exhibits an efficient power conversion efficiency (PCE) of 3.60%.

Dithienothiophene 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

>98% Purity

General Information

CAS Number	67061-69-2
Chemical Formula	C₈H₂Br₂S₃
Full Name	2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene
Molecular Weight	354.1 g/mol
Synonyms	DTT-2Br
Classification / Family	Thienothiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR in CDCl₃)
Melting Point	171.0 °C
Appearance	Fluffy white/off white powder

MSDS Documentation

2,6-Dibromodithieno[3,2-b:2′,3′-d]thiophene MSDS Sheet

Literature and Reviews

Novel copolymers incorporating dithieno[3,2-b:2′,3′-d]thiophene moieties for air-stable and high performance organic field-effect transistors, K. Lu et al., J. Mater. Chem., 18, 3426-3432 (2008); DOI: 10.1039/B801603H.
D-π-D Chromophores based on Dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell, C. Wang et al., Tetrahedron 73 (4), 307-312 (2017); DOI: 10.1016/j.tet.2016.11.077.
Improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene (DTT) and derivatives for cross coupling, J. Frey et al., Chem. Commun., 2424-2425 (2022); DOI: 10.1039/B207403F.

Vacuum processable donor material based on dithieno[3,2-b:2′,3′-d]thiophene and pyrene for efficient organic solar cells, J. Kwon et al., RSC Adv., 4, 24453-24457 (2014); DOI: 10.1039/C4RA02895C.
Solution-processable multicolored dithienothiophene-based conjugated polymers for electrochromic applications, W. Neo et al., Eur. Polym. J. 49 (9), 2446-2456 (2013); DOI: 10.1016/j.eurpolymj.2013.02.026.
High-Performance and Stable Organic Thin-Film Transistors Based on Fused Thiophenes, Adv. Funct. Mater., 16 (3), 426-432 (2006); Y. Sun et al., DOI: 10.1002/adfm.200500547.
The synthesis, characterization and flexible OFET application of three (Z)-1,2-bis(4-(tert-butyl)phenyl)ethane based copolymers, Y. Huang et al., Polym. Chem., 7, 538-545 (2016); DOI: 10.1039/C5PY01647A.
Synthesis, Characterization and Field-Effect Transistor Performance of Benzoannulated Pentathienoacene Derivative, X. Qi et al., New J. Chem., 39, 1045-1050 (2015); DOI: 10.1039/C4NJ01590H.
Color Fine-Tuning of Optical Materials Through Rational Design, B. Holzer et al., ChemPhysChem, 18 (5), 549-563 (2017); DOI: 10.1002/cphc.201601204.
Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide, Z. Fei et al., Macromolecules, 49, 17, 6384–6393 (2016); DOI: 10.1021/acs.macromol.6b01423.