2,6-Dibromonaphthalene

CAS Number 13720-06-4

Chemistry Building Blocks, Dibromo Monomers, Materials, Monomers, Non-Heterocyclic Building Blocks

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.

Specifications | MSDS | Literature and Reviews

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 (E_bg = 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 T_g 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.

Naphthalene building block

for the synthesis of OLED and organic photovoltaic materials

Worldwide shipping

Quick and reliable shipping

Capped with bromides

for facile coupling reactions

High purity

>98% Purity

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

Product Details

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

MSDS Documentation

2,6-Dibromonaphthalene MSDS Sheet

Literature and Reviews

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.
A Wide Band Gap Naphthalene Semiconductor for Thin-Film Transistors, L. Yan et al., 3 (5), 1600556 (2017); DOI: 10.1002/aelm.201600556.
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.

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.
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.
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.
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.
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.
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.