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2,6-Dibromonaphthalene  CAS 13720-06-4
Product Code B1321-5g
Price £185 ex. VAT
£ GBP

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A double brominated naphthalene intermediate

Used for the preparation of semiconducting molecules in application of thin-film transistors, cathode Interfacial material and non-fullerene acceptors for OPVs, and hole-transporting hosts for OLEDs.

2,6-Dibromonaphthalene (2,6-DBN), CAS number 13720-06-4, is another double brominated naphthalene derivatives that is used as a building block for constructing small semiconducting molecules or polymers in application of organic photovoltaics, OLEDs and OFETs devices.

2,6-Di(anthracen-2-yl)naphthalene (2,6-DAN) single crystals, obtained by using 2,6-dibromonaphthalene as one of the starting materials, showed bright yellowish-green emission and well-balanced ambipolar charge transport. Moreover, 2,6-di(anthracen-2-yl)naphthalene exhibited charge mobility of up to 19 cm2 V-1 and an absolute fluorescence quantum yield of 37.09% [1]. Organic field-effect transistors based on large bandgap (Ebg = 3.35 eV) organic semiconductor 2,6-bis(4-methoxyphenyl)naphthalene (BOPNA) exhibited a hole mobility of ~1 cm2 V-1 with complete optical transparency in the visible range (>370 nm), very high stability and independence of the device current with illumination conditions.

 Phen-NaDPO, bearing a triarylphosphine oxide and a 1,10-phenanthrolinyl unit with naphthalene core possesses a high Tg of 116 °C and attractive electron-transport properties. Phen-NaDPO as a promising cathode interlay material can significantly lower the work function of the Ag metal as well as ITO, and facilitate electron extraction thus considerably improve the PCE of OPV devices.

General Information

CAS Number 13720-06-4
Chemical Formula C10H6Br2
Full Name 2,6-Dibromonaphthalene
Molecular Weight 285.97 g/mol
Synonyms 2,6-DBN
Classification / Family Naphthalenes, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

2,6-Dibromonaphthalene chemical structure
2,6-Dibromonaphthalene (2,6-DBN) chemical structure, CAS 13720-06-4

Product Details

Purity >98% (1H NMR)
Melting Point Tm = 162 °C
Appearance White to yellow, pale beige to beige, pale brown to brown powder/crystals

MSDS Documentation

2,6-Dibromonaphthalene2,6-Dibromonaphthalene MSDS Sheet

Literature and Reviews

  1. Molecular-scale integrated multi-functions for organic light-emitting transistors, L. Zheng et al., Nano Res. 13, 1976–1981 (2020); DOI: 10.1007/s12274-020-2851-4.
  2. A Wide Band Gap Naphthalene Semiconductor for Thin-Film Transistors, L. Yan et al., 3 (5), 1600556 (2017); DOI: 10.1002/aelm.201600556.
  3. Lending Triarylphosphine Oxide to Phenanthroline: a Facile Approach to High-Performance Organic Small-Molecule Cathode Interfacial Material for Organic Photovoltaics utilizing Air-Stable Cathode, W. Tan et al., Adv. Funct. Mater., 24 (41), 6540-6547 (2014); DOI: 10.1002/adfm.201401685.
  4. A novel acceptor with a N,N-dialkyl thieno[3′,2′:2,3]indolo[7,6-g]thieno[3,2-b]indole (TITI) core for organic solar cells with a high fill factor of 0.75, X. Zhang et al., Chem. Commun., 56, 751-753 (2020); DOI: 10.1039/C9CC08098H.
  5. Study of Energy Transfer and Triplet Exciton Diffusion in Hole-Transporting Host Materials, C. Wu et al., Adv. Funct. Mater., 19 (19), 3157-3164 (2009); DOI: 10.1002/adfm.200900357.
  6. Fluorescence Emission from 2,6-Naphthylene-Bridged Mesoporous Organosilicas with an Amorphous or Crystal-Like Framework, N. Mizoshita et al., Chem. Eur. J. 15 (1), 219-226 (2008); DOI: 10.1002/chem.200801238.
  7. Syntheses of Ladder-Type Oligonaphthalene Derivatives and Their Photophysical and Electrochemical Properties, J. Chen et al., Chem. Eur. J. 14 (9), 2777-2787 (2008); DOI: 10.1002/chem.200700830.
  8. Structure property relationships of benzo[b]thiophen/benzo[b]furan end-capped naphthalene oligomers and their application for organic field effect transistors, Y. Wang et al., RSC Adv., 5, 31018-31023 (2015); DOI: 10.1039/C5RA03659C.
  9. Crystallinity-Controlled Naphthalene-alt-diketopyrrolopyrrole Copolymers for High-Performance Ambipolar Field Effect Transistors, H. Lee et al., J. Phys. Chem. C, 116 (50), 26204–26213 (2012); DOI: 10.1021/jp309213h.
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