5,5'-Dibromo-2,2'-bipyridine

CAS Number 15862-18-7

Chemistry Building Blocks, Dibromo Monomers, Heterocyclic Building Blocks, Monomers

5,5'-Dibromo-2,2'-bipyridine CAS 15862-18-7

A well-known bipyridine ligand with two bromo-functional groups

A bidentate ligand for organometallic compound in application of OLEDs, DSSCs and photosensitisers

Overview
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5,5'-Dibromo-2,2'-bipyridine (CAS number 15862-18-7), derived from bipyridine, is a bromine functionalized building block with popular use as a chelating ligand for ruthenium (Ru) or iridium (Ir) organometallic complexes. Bipyridine-Ru complexes exhibit excellent photoluminescence and electrochemiluminescence for OLEDs and DSSCs, owing to the strong intraligand (π-π*) and metal-ligand charge transfer (MLCT) transition bands.

Bearing dibromo function groups, 5,5'-Dibromo-2,2'-bipyridine allows further functionalization to form larger conjugated molecules. Bipyridine derivatives can react with borane species to form organoboron compounds as electron acceptor in organic photovoltaics. By extending the chromophore size of the bipyridine core, these types of ligands are employed as photosensors for the detection of fluoride ions. This linear building block is also ideal for bridging different functional molecules for modifying energy band gap and intramolecular spacing.

General Information

CAS Number	15862-18-7
Chemical Formula	C₁₀H₆Br₂N₂
Full Name	5,5'-Dibromo-2,2'-bipyridine
Molecular Weight	313.98 g/mol
Synonyms	5-bromo-2-(5-bromopyridin-2-yl)pyridine
Classification / Family	Bipyridine derivatives, Heterocyclic building blocks, Dyes, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	T_m = 226 - 227 °C
Appearance	Off-white powder

MSDS Documentation

5,5'-Dibromo-2,2'-bipyridine MSDS Sheet

Literature and Reviews

Synthesis, photoluminescence and electrochemiluminescence of ruthenium(II) polypyridyl complexes based on bipyridine derivatives with carbazole moieties, H. -Y. Li et al., Inorg. Chim. Acta., 370, 398-404(2011); DOI: 10.1016/j.ica.2011.02.012.
Heteroleptic ruthenium complexes containing uncommon 5,5'-disubstituted-2,2'-bipyridine chromophores for dye-sensitized solar cells, F.-R. Dai et al., Dalton Trans., 40, 2314–2323(2011); DOI: 10.1039/c0dt01043j.
Oligomeric ligands incorporating multiple 5,5'-diethynyl-2,2'-bipyridine moieties bridged and end-called by 3,4-dibutylthiophene units, S. Goeb et al., J. Org. Chem., 70, 1518-1529(2005); DOI: 10.1021/jo048435i.
An organoboron compound with wide absorption spectrum for solar cell application, F. Liu et al., Chem. Commun., 53, 12213-12216(2017); DOI: 10.1039/C7CC07494H.
Replacement of biphenyl by bipyridine enabling powerful hole transport materials for efficient perovskite solar cells with high V_oc and FF, F. Wu et al., ChemSusChem, 10,3833–3838(2017); DOI: 10.1002/cssc.201700973.
A highly efficient red-emitting ruthenium complex with 3,5-difluorophenyl substituents, Y. Zhu et al., ChemPlusChem, 81, 73–79(2016); DOI: 10.1002/cplu.201500346.
Conjugated triarylboryl donor-acceptor systems supported by 2,2'-bipyridine: metal chelation impact on intraligand charger transfer emission, electron accepting ability, and “turn-on” fluoride sensing, Y. Sun et al., Inorg. Chem., 48(8), 3755-3767(2009); DOI: 10.1021/ic9000335.
Synthesis of a linear bis-porphyrin with a Ru(phen)₂²⁺-complexed 2,2'-bipyridine spacer, J. Bruce et al., J. Chem. Soc., Perkin Trans., 1, 1226–123(2002); DOI: 10.1039/b202407c.

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