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Product Code B1461-5g
Price £110 ex. VAT

A widely used electron deficient anthraquinone building block

For the synthesis of semiconducting small molecules or polymers in application of fluorophores, photocatalyst, OLEDs and organic solar cells

Specifications | MSDS | Literature and Reviews

2,6-Dibromoanthraquinone (CAS number 633-70-5) has an electron deficient structure of anthracene-9,10-dione with bromo substituents at 2,6-position of the anthraquinone ring. Both the bromo and 9,10-dione functional groups enable the anthracene core to extend its conjugation for the preparation of more complex structures, i.e., semiconducting small molecules or polymers in application of fluorophores, photocatalyst, OLEDs and organic solar cells.

Containing anthraquinone center prepared by cross-coupling reaction between 2,6-dibromoanthraquinone and 1,1,2,2-tetrakis(4-ethynylphenyl)ethene, conjugated organic polymer (AQTEE-COP) demonstrated efficient photocatalytic H2O2 production with an initial rate of 3204 μmol g-1 h-1 under visible light (λ ≥ 400 nm) irradiation without any additional photosensitizers, organic scavengers, or co-catalysts.

Developed for bioimaging in the NIR-II window, novel donor–acceptor–donor type second near-infrared AIE fluorophores AQMN, based on strong electron-acceptor 2,2′-(anthracene-9,10-diylidene) dimalononitrile which was also derived from 2,6-dibromoanthraquinone, exhibit good photostability and can be used in mouse ear vessel imaging with high resolution (FWHM = 93.4 μm/SBR = 1.5) after capsuling in nanoparticles with good biocompatibility.

General Information

CAS Number 633-70-5
Chemical Formula C14H6Br2O2
Full Name 2,6-Dibromoanthraquinone
Molecular Weight 366.01 g/mol
Synonyms 2,6-DBAQ, 2,6-Dibromoxyanthracene-9,10-dione
Classification / Family Anthraquinone derivatives, Dyes, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

2,6-Dibromoanthraquinone chemical structure, 633-70-5
2,6-Dibromoanthraquinone (2,6-DBAQ) CAS 633-70-5

Product Details

Purity >96% (1H NMR)
Melting Point Tm = 290 °C (lit.)
Appearance Yellow/brown powder

MSDS Documentation

2,6-dibromoanthraquinone2,6-Dibromoanthraquinone MSDS Sheet

Literature and Reviews

  1. Aggregation-induced emission fluorophores based on strong electron-acceptor 2,2′-(anthracene-9,10-diylidene) dimalononitrile for biological imaging in the NIR-II window, Z. Yang et al., Chem. Commun., 57, 3099-3102 (2021); DOI: 10.1039/D1CC00742D.
  2. New Anthraquinone-Based Conjugated Microporous Polymer Cathode with Ultrahigh Specific Surface Area for High-Performance Lithium-Ion Batteries, A. Molina et al., Adv. Funct. Mater., 30 (6), 1908074 (2020); DOI: 10.1002/adfm.201908074.
  3. Anthraquinone-Enriched Conjugated Microporous Polymers as Organic Cathode Materials for High-Performance Lithium-Ion Batteries, M. Moharmed et al., ACS Appl. Energy Mater., 4 (12), 14628–14639 (2021); DOI: 10.1021/acsaem.1c03270.
  4. Synthesis and Characterization of a New Series of Blue Fluorescent 2,6-Linked 9,10-Diphenylanthrylenephenylene Copolymers and Their Application for Polymer Light-Emitting Diodes, H. Chen et al., Macromolecules, 43 (8), 3613–3623 (2010); DOI: 10.1021/ma100195m.
  5. Triphenylamine–anthraquinone based donor–acceptor conjugated microporous polymers for photocatalytic hydroxylation of phenylboronic acids, S. Sau et al., Chem. Commun., 59, 635-638 (2023); DOI: 10.1039/D2CC05334A.
  6. Highly Crystalline 2,6,9,10-Tetrakis((4-hexylphenyl)ethynyl)anthracene for Efficient Solution-Processed Field-effect Transistors, J. Hur et al., Bull. Korean Chem. Soc., 33 (5), 1653-1658 (2012); DOI: 10.5012/bkcs.2012.33.5.1653.
  7. Synthesis and Characterizations of Poly(9,10-bisarylethynyl-2,6-anthrylene)s and Poly(9,10-bisalkynyl-2,6-anthrylene), W Cui et al., Macromolecules, 42 (21), 8021–8027 (2009); DOI: 10.1021/ma901514q.
  8. Conjugated Organic Polymers with Anthraquinone Redox Centers for Efficient Photocatalytic Hydrogen Peroxide Production from Water and Oxygen under Visible Light Irradiation without Any Additives, X. Xu et al., ACS Catal., 12 (20), 12954–12963 (2022); DOI: 10.1021/acscatal.2c04085.
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