4,4'-Dibromo-2,2'-bipyridine

CAS Number 18511-71-2

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

4,4'-Dibromo-2,2'-bipyridine CAS 18511-71-2

A popular bipyridyl building blocks

Used for the synthesis of hole transport layers and photosensitizers for OLEDs and OPVs

Specifications | MSDS | Literature and Reviews

4,4'-Dibromo-2,2'-bipyridine (DBrBPy, CAS number 18511-71-2) is a 4,4'-brominated bipyridyl derivative joined at 2,2'-positions. 4,4'-Dibromo-2,2'-bipyridine is electron deficient and normally used as a ligand for the synthesis of organometallic compounds, i.e., ruthenium (II) photosensitizers.

Organic semiconductor with an electron withdrawing bipyridine core and triarylamine electron donating moieties can act as an efficient tunnel between perovskite and a hole transporting layer. It is believed that the bipyridine core can passivate the uncoordinated Pb²⁺ defects of perovskite films. As a result, the hole mobility of the hole transporting layer was increased by 7 times, from 1.05 × 10^-4 to 8.36 × 10^-4 cm² V^-1 s^-1 and the power conversion efficiency (PCE) of n–i–p structured perovskite solar cells was boosted with improved stability [1].

2,2′-bipyridine bearing two corannulenes at 4.4-positions can act as molecular tweezers for fullerene recognition. The syn or anti confirmation can be selected simply by Cu(I) coordination/decoordination, thus managing the fullerene recognition capability of the system on demand [2].

General Information

CAS Number	18511-71-2
Chemical Formula	C₁₀H₆Br₂N₂
Full Name	4,4'-Dibromo-2,2'-bipyridine
Molecular Weight	313.98 g/mol
Synonyms	4,4'-Dibromo-2,2'-bipyridyl, DBrBPy
Classification / Family	Bipyridine derivatives, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	T_m = 138 °C
Appearance	White powder

MSDS Documentation

4,4'-Dibromo-2,2 -dipyridine MSDS Sheet

Literature and Reviews

A highly efficient interface hole transporting tunnel by a bipyridine semiconductor for perovskite solar cells, J. Mater. Chem. C, 10, 18069-18076 (2022); DOI: 10.1039/D2TC03649E.
ON/OFF metal-triggered molecular tweezers for fullerene recognition, A. Sacristán-Martín, Chem. Commun., 57, 11013 (2021); DOI: 10.1039/d1cc03451k.
Synthesis, properties, and OLED characteristics of 2,2′-bipyridine-based electron-transport materials: the synergistic effect of molecular shape anisotropy and a weak hydrogen-bonding network on molecular orientation, Y. Watanabe et al., J. Mater. Chem. C, 4, 3699-3704 (2016); DOI: 10.1039/C5TC03737A.

Synthesis of 2,2′-bipyridine-containing polymers: synthesis of poly[2,2′-bipyridine-4,4′-diylethynylene-(2,5-dialkoxy-1,4-phenylene)ethynylene], D. Egbe et al., Des. Monomers Polym., 3 (3), 289–297 (2000)DOI: 10.1163/156855500300160249.
Synthesis, structural analysis, and supramolecular assembly of a series of in situ generated uranyl–peroxide complexes with functionalized 2,2′-bipyridine and varied carboxylic acid ligands, J. Ridenour et al., New J. Chem., 42, 1816-1831 (2018); DOI:10.1039/C7NJ03828C.
Synthesis, X-ray structure, antiproliferative activity, interaction with HSA and docking studies of three novel mono and binuclear copper complexes containing the maltol ligand, M. Eraj et al., New J. Chem., 44, 20101-20114 (2020); DOI: 10.1039/D0NJ03552A.
Regulating Utilization Efficiency of the Photogenerated Charge Carriers by Constructing Donor–π–Acceptor Polymers for Upgrading Photocatalytic CO2 Reduction, J. Chen et al., ChemSusChem, 14, 2749 – 2756 (2021); DOI: 0.1002/cssc.202100772.
Green–Solvent–Processable Perovskite Solar Cells, Y. Cui et al., Adv. Energy Sustainability Res., 2, 2000047 (2021); DOI: 10.1002/aesr.202000047.