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.
2,8-Dibromodibenzothiophene is a double brominated derivative of dibenzothiophene which structurelly 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.
2,8-Dibromodibenzothiophene was synthesised from dibenzothiophen 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 currrent efficency of 42 cd/A while hosting Firpic as blue emitting OLEDs with the following device structure:
|Molecular weight||342.05 g/mol|
|Classification / Family||Dibromodibenzothiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Melting point||Tm = 226 °C|
|Appearance||White to off-white powder/crystals|
MSDS Documentation2,8-Dibromodibenzothiophene MSDS Sheet
Literature and Reviews
High-Mobility Regioisomeric Thieno[f,f′]bisbenzothiophenes: 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.
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