9-Bromoanthracene

CAS Number 1564-64-3

Chemistry Building Blocks, Monomers, Non-Heterocyclic Building Blocks

9-Bromoanthracene, a key intermediate

Used for the synthesis of polycyclic aromatic hydrocarbons (PAH) in application of OLEDs.

Overview
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9-Bromoanthracene (CAS number 1564-64-3) is a mono-brominated anthracene at 9-position. It is one of the key intermediates for the construction of polycyclic aromatic hydrocarbon (PAH) anthracene. Photodimers of 9-bromoanthracene are suitable alkyl halide initiators in the atom transfer radical polymerization (ATRP) reactions

Non-doped device based on 9-bromoanthracene derived DCPA-TPA provides NIR emission with peaks at 838 nm and a maximum radiance of 20707 mW Sr^-1 m^-2 was observed for the optimized device based on DCPA-TPA [1]. Also doping device using 3,6-di(anthracen-9-yl)-9-phenyl-9H-carbazole (P-DAC) as the host material showed high luminance efficiencies and external quantum efficiencies of as high as 7.70 cd A^-1 and 4.86% with CIE chromaticity coordinates (0.156, 0.136) and 100 mA cm^-2 [2].

General Information

CAS Number	1564-64-3
Chemical Formula	C₁₄H₉Br
Full Name	9-Bromoanthracene
Molecular Weight	257.13 g/mol
Synonyms	Anthracene, 9-bromo-
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 = 105 °C
Appearance	Yellow to orange powder/crystals

MSDS Documentation

9-Bromoanthracene MSDS Sheet

Literature and Reviews

Near-Infrared Electroluminescence beyond 800 nm with High Efficiency and Radiance from Anthracene Cored Emitters, Y. Yu et al., Angew. Chem. Intl. Ed., 59 (48), 21578-21584 (2020); DOI: 10.1002/anie.202006197.
Highly efficient deep-blue emitting organic light emitting diode based on the multifunctional fluorescent molecule comprising covalently bonded carbazole and anthracene moieties, S. Kim et al., J. Mater. Chem., 21, 9139-9148 (2011); DOI: 10.1039/C1JM11111F.
Characterization and properties of a novel energetic Co-crystal formed between 2,4,6-Trinitrophenol and 9-Bromoanthracene, S. Bozkuş et al., J. Mol. Struct., 1192, 145-153 (2019); DOI: 10.1016/j.molstruc.2019.04.109.
Design, Synthesis, and Temperature-Driven Molecular Conformation-Dependent Delayed Fluorescence Characteristics of Dianthrylboron-Based Donor–Acceptor Systems, U. Pandey et al., Front. Chem., 8, 541331 (2020); DOI: 10.3389/fchem.2020.541331.
Efficient Solution-Processed Nondoped Deep-Blue Organic Light-Emitting Diodes Based on Fluorene-Bridged Anthracene Derivatives Appended with Charge Transport Moieties, M. Zhu et al., J. Phys. Chem. C, 115 (36), 17965–17972 (2011);
Efficient blue organic light-emitting diode using anthracene-derived emitters based on polycyclic aromatic hydrocarbons, J. Bin et al., Org. Electron., 12 (5), 802-808 (2011); DOI: 10.1016/j.orgel.2011.02.011.
Pincer CNC bis-N-heterocyclic carbenes: robust ligands for palladium-catalysed Suzuki–Miyaura arylation of bromoanthracene and related substrate, V. Zende et al., Org. Chem. Front., 2, 1397-1410 (2015); DOI: 10.1039/C5QO00236B.
A new cross-linkable 9,10-diphenylanthracene derivative as a wide bandgap host for solution-processed organic light-emitting diodes, R. Hallani et al., J. Mater. Chem. C, 6, 12948-12954 (2018); DOI: 10.1039/C8TC05013A.

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