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Product Code B1251-1g
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Dihalogenated naphthalene compound can be a suitable host for fluorescent polycyclic aromatic hydrocarbons molecules

Also used as a building block leading to more complex structures in application of organic electronics.

2,3-Dibromonaphthalene (2,3-DBN) is another useful intermediate and isomer of dibromonaphthalene with two heavy bromo substituents sitting next to each other around the naphthalene ring.

X-ray diffraction analysis shows that the crystal structure of 2,3-dibromonaphthalene is ordered where the weak and directional forces generate the herringbone packing of the constituting molecules. For this reason, 2,3-dibromonaphthalene is employed as a suitable host for fluorescent  polycyclic aromatic hydrocarbons (PAH) molecules. Single molecules of terrylene in 2,3-dibromonaphthalene crystallise also in a herringbone pattern, directed by the 2,3-dibromonaphthalene host.

General Information

CAS Number 13214-70-5
Chemical Formula C10H6Br2
Full Name 2,3-Dibromonaphthalene
Molecular Weight 285.97 g/mol
Synonyms 2,3-DBN
Classification / Family Naphthalenes, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

2,3-dibromonaphthalene chemical structure, 13214-70-5
2,3-Dibromonaphthalene (2,3-DBN) chemical structure, CAS 13214-70-5

Product Details

Purity >98% (1H NMR)
Melting Point Tm = 142 °C
Appearance White to off-white powder/crystals

MSDS Documentation

2,3-Dibromonaphthalene2,3-Dibromonaphthalene MSDS Sheet

Literature and Reviews

  1. A Highly Warped Heptagon-Containing sp2 Carbon Scaffold via Vinylnaphthyl π-Extension, J. Farrell et al., Angew.Chem., 131, 16656–16659 (2019); DOI:10.1002/ange.201909975.
  2. Matrix-induced Linear Stark Effect of Single Dibenzoterrylene Molecules in 2,3-Dibromonaphthalene Crystal, A. Moradi et al., ChemPhysChem, 20,55–61 (2019); DOI: 10.1002/cphc.201800937.
  3. Spectra and nature of the electronic excited states of 2,3-dibromonaphthalene single crystals, I. Deperasińska et al., J. Lumin., 213, 108-116 (2019); DOI: 10.1016/j.jlumin.2019.05.011.
  4. A convenient generation of 2,3-naphthalyne. Linear annulation of naphthalene and a new naphthacene synthesis, C. LeHoullier et al., J. Org. Chem., 48, 14, 2364–2366 (1983); DOI: 10.1021/jo00162a013.
  5. Synthesis of 2,3-dialkyl-6,7-dichloro- and 2,3-dialkyl-6,7-dibromo-1,4-naphthoquinones, A. Ashnagar et al., J. Chem. Soc., Perkin Trans., 1, 559-561 (1988); DOI: 10.1039/P19880000559.
  6. Synthesis of tetraaryl-p-benzoquinones and 2,3-diaryl-1,4-naphthoquinones via Suzuki–Miyaura cross-coupling reactions, Z. Hassan et al., Tetrahedron, 69 (2), 460-469 (2013); DOI: 10.1016/j.tet.2012.11.040.
  7. Synthesis of Substituted Dibenz[a,c]anthracenes and an Investigation of Their Liquid-Crystalline Properties, K. Psutka et al., Eur. J. Org. Chem., 2015 (7), 1456-1463 (2015); DOI: 10.1002/ejoc.201403504.
  8. Single organic molecules for photonic quantum technologies, C. Toninelli et al., Nat. Mater. 20, 1615–1628 (2021); DOI: 10.1038/s41563-021-00987-4.
  9. Laser-Induced Frequency Tuning of Fourier-Limited Single-Molecule Emitters, M. Colautti et al., ACS Nano, 14, 10, 13584–13592 (2020); DOI: 10.1021/acsnano.0c05620.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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