2,3-Dibromonaphthalene
CAS Number 13214-70-5
Chemistry Building Blocks, Monomers, Non-Heterocyclic Building Blocks
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), CAS number 13214-70-5, 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
Product Details
Purity | >98% (1H NMR) |
Melting Point | Tm = 142 °C |
Appearance | White to off-white powder/crystals |
MSDS Documentation
2,3-Dibromonaphthalene MSDS Sheet
Literature and Reviews
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- Single organic molecules for photonic quantum technologies, C. Toninelli et al., Nat. Mater. 20, 1615–1628 (2021); DOI: 10.1038/s41563-021-00987-4.
- 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.
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