9,10-Dibromoanthracene

CAS Number 523-27-3

Chemistry Building Blocks, Dibromo Monomers, Monomers, Non-Heterocyclic Building Blocks

One of anthracene derivatives that is brominated at 9,10-postions

A useful building block to construct semiconducting molecules and polymers in application of OFETs, OLEDs and organic polymer solar cells.

Overview
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9,10-Dibromoanthracene (CAS number 523-27-3) is a symmetrically brominated anthracene derivative that is bearing functional groups to extend its conjugation further mainly via C-C bond forming i.e. Stille and Suzuki coupling reactions. Anisotropic Poisson effect is observed in elastic 9,10-dibromoanthracene single crystals. Its bending and stretching deformation-induced fluorescence changes are observed in the solid state.

High photoluminescence quantum yields (PLQYs) of 89.5% was observed in trans-9,10-bis(2-butoxyphenyl)anthracene (BBPA). Device efficiency of a high external quantum efficiency of 10.27% for deep-blue emission with the Commission International de L'Eclairage CIE coordinates of (0.15, 0.05) was acheieved with BBPA doped 10,10′-bis-(4-fluorophenyl)-3,3′-dimethyl-9,9′-bianthracene (MBAn-(4)-F) as the emmision layer [1].

General Information

CAS Number	523-27-3
Chemical Formula	C₁₄H₈Br₂
Full Name	9,10-Dibromoanthracene
Molecular Weight	336.03 g/mol
Synonyms	Anthracene, 9,10-dibromo-
Classification / Family	Anthracenes, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	T_m = 227 °C
Appearance	Yellow to orange powder/crystals

MSDS Documentation

9,10-Dibromoanthracene MSDS Sheet

Literature and Reviews

Efficient Deep-Blue Electrofluorescence with an External Quantum Efficiency Beyond 10%, S. Wang et al., IScience, 9, 532-541 (2018); DOI: 10.1016/j.isci.2018.10.026.
Highly efficient non-doped blue fluorescent OLEDs with low efficiency roll-off based on hybridized local and charge transfer excited state emitters, X. Lv et al., Chem. Sci., 11, 5058-5065 (2020); DOI: 10.1039/D0SC01341B.
Silicon-Cored Anthracene Derivatives as Host Materials for Highly Efficient Blue Organic Light-Emitting Devices, Y.-Y. Lyu et al., Adv. Mater., 20, 2720–2729 (2008); DOI: 10.1002/adma.200602885.
Anisotropic Poisson Effect and Deformation-Induced Fluorescence Change of Elastic 9,10-Dibromoanthracene Single Crystals, S. Hayashi et al., Angew. Chem., Int. Ed., 59(37), 16195-16201 (2020); DOI:10.1002/anie.202006474.
An improved procedure for the preparation of 9, 10-dibromoanthracene, S. Jones et al., Synth. Commun., 31:12, 1799-1802 (2006); DOI: 10.1081/SCC-100104326.
Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives, O. Cakmak et al., Beilstein J. Org. Chem., 4 (50), 2008; https://doi.org/10.3762/bjoc.4.50.
Synthesis, Photophysical Properties, and Field-Effect Characteristics of (Ethynylphenyl)benzimidazole-Decorated Anthracene and Perylene Bisimide Derivatives, I.-L.. Lee et al., Eur. J. Org. Chem., 2906–2915 (2012); DOI: 10.1002/ejoc.201200032.
Copolymers of 4-thieno[3,2-b]thiophen-3-ylbenzonitrile with anthracene and biphenyl; synthesis, characterization, electronic, optical, and thermal properties, R. Isci et al., J Polym Sci., 59:117–123 (2021); DOI: 10.1002/pol.20200635.
Small Molecular Aryl Acetylenes: Chemically Tailoring High-Efficiency Organic Semiconductors for Solar Cells and Field-Effect Transistors, A. Broggi et al., ChemPlusChem, 79, 2 – 24 (2014); DOI: 10.1002/cplu.201400001.
Molecular-Shape-Controlled Photovoltaic Performance Probed via Soluble π-Conjugated Arylacetylenic Semiconductors, M. Seri et al., Adv. Mater., 23, 3827–3831 (2011); DOI: 10.1002/adma.201101700.

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