2,8-Dibromodibenzothiophene

CAS Number 31574-87-5

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

2,8-Dibromodibenzothiophene CAS 31574-87-5

High-Quality 2,8-Dibromodibenzothiophene

A useful building block for the further synthesis of small molecules, oligomers and polymers either as host for phosphorescent dyes, electron transport layer or active layer materials for OLEDs, OFETs and OPVs.

Specifications | MSDS | Literature and Reviews

2,8-Dibromodibenzothiophene (CAS number 31574-87-5) is a double brominated derivative of dibenzothiophene which structurally can be considered as a biphenyl further bridged with a sulfur atom. The numbering of dibenzothiophene ring is somewhat confusing when it is compared with the numbering of carbazole.

numbering of dibenzothiophene ring — Numbering of dibenzothiophene ring

2,8-Dibromodibenzothiophene was synthesised from dibenzothiophene with bromine in chloroform. Further oxidation of 2,8-dibromodibenzothiophene with dihydrogen peroxide In acetic acid gives 2,8-dibromodibenzothiophene- 5,5-dioxide. Solution-processed OFETs using the syn-TBBT, prepared from 2,8-dibromodibenzothiophene as the starting material, show high hole mobilities of up to 10.1 cm² V^-1s^-1. Water-soluble π-conjugated small molecules based on dibenzothiophene-S,S-dioxide and bispyridinium salts, FSOPyCl and FSOmiCl, show large planarity, good thermal stability, excellent electron affinity and high fluorescence efficiency. Ambipolar phosphorescent host and electron transport layer material 2,8-Bis(diphenyl-phosphoryl)-dibenzo[b,d]thiophene (PPT), also a derivate of 2,8-dibromodibenzothiophene, yields a power efficiency of 30 lm W^-1 and current efficiency of 42 cd/A while hosting FIrPic as blue emitting OLEDs with the following device structure:

ITO/TAPC (40 nm)/TCTA (2 nm)/26DCzPPy:TCTA:FIrPic (0.4:0.4:0.2) (5 nm)/26DCzPPy:PPT:FIrpic (0.4:0.4:0.2) (5 nm)/3TPYMB (55 nm)/CsF (2 nm)/Al (180 nm)

Dibenzothiophene 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

>99% Purity

General Information

CAS Number	31574-87-5
Chemical Formula	C₁₂H₆Br₂S
Full Name	2,8-Dibromodibenzo[b,d]thiophene
Molecular Weight	342.05 g/mol
Synonyms	DBDBT 2,8-Dibromo Dibenzothiophene
Classification / Family	Dibromodibenzothiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>99% (HPLC)
Melting point	T_m= 226 °C
Appearance	White to off-white powder/crystals

MSDS Documentation

2,8-Dibromodibenzothiophene MSDS sheet

Literature and Reviews

High-Mobility Regioisomeric Thieno[f,f′]bis[1]benzothiophenes: Remarkable Effect of Syn/Anti Thiophene Configuration on Optoelectronic Properties, Self-Organization, and Charge-Transport Functions in Organic Transistors, T. Oyama et al., Adv. Funct. Mater., 4 (1), 1700390 (2018); DOI: 10.1002/aelm.201700390.
Dipolar Dibenzothiophene S,S-Dioxide Derivatives Containing Diarylamine: Materials for Single-Layer Organic Light-Emitting Devices, T. Huang et al., Adv. Mater., 18, 602–606 (2006); DOI: 10.1002/adma.200502078.
Organic electroluminescent derivatives containing dibenzothiophene and diarylamine segments, T. Huang et al., J. Mater. Chem., 15, 3233–3240 (2005); DOI: 10.1039/b507210.

Synthesis and optical and electrochemical properties of water-soluble cationic fluorophores based on bispyridinium and dibenzothiophene-S,S-dioxide, G. Chen et al., New J. Chem., 41, 1696-1703 (2017); DOI: 10.1039/C6NJ03108K.
Dibenzothiophene derivatives as host materials for high efficiency in deep blue phosphorescent organic light emitting diodes, S. Jeong et al., J. Mater. Chem., 21, 14604-14609 (2011); DOI: 10.1039/C1JM12421H.
Blue and white phosphorescent organic light emitting diode performance improvementbyconfining electrons and holes inside double emitting layers, Y-S.Tsai et al., J. Luminescence 153, 312–316 (2014); doi: 10.1016/j.jlumin.2014.03.040.