4,4'-Dimethyl-2,2'-bipyridyl

CAS Number 1134-35-6

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

4,4'-Dimethyl-2,2'-bipyridyl CAS 1134-35-6

A well-known bipyridyl ligand with two methyl groups

Readily available for the synthesis of organometallic photosensitizer dyes in development of dye-sensitized solar cells (DSSCs)

Overview
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4,4'-Dimethyl-2,2'-bipyridyl (CAS number 1134-35-6), derived from bipyridine and also bearing electron rich methyl functional groups at 4,4'-positions, is typically used as a starting material for the sensitizers synthesis in dye sensitized solar cells (DSSCs).

Bipyridine ligand is a strong chelating ligand for metal centres in coordinative compounds. The organometallic compound of 4,4'-dimethyl-2,2'-bipyridyl increases the bridging ligand lengths resulting a greater electron-hole separation effect in DSSCs, hence reduce charge recombination to improve the overall device efficiency. High device efficiencies engaging 4,4'-dimethyl-2,2'-bipyridyl coordinative dyes are attributed to efficient light harvesting of these novel dyes and the improved charge transfer dynamics at TiO₂–dye and dye–hole transport interfaces.

4,4'-Dimethyl-2,2'-bipyridyl is also used for fabricating electrochemiluminescence (ECL) materials. It enhances the ECL intensity owing to the donor ability as a α-diimine ligands.

General Information

CAS Number	1134-35-6
Chemical Formula	C₁₂H₁₂N₂
Full Name	4,4'-Dimethyl-2,2'-bipyridyl
Molecular Weight	184.24 g/mol
Synonyms	2,2′-Bi(γ-picoline), 4,4′-Dimethyl-2,2′-bipyridine
Classification / Family	Bipyridyl derivatives, Semiconductor synthesis intermediates, Heterocyclic building blocks, Dye-sensitized solar cells (DSSCs)

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	T_m = 169 - 174 °C
Appearance	Pale pink powder

MSDS Documentation

4,4'-Dimethyl-2,2'-bipyridyl MSDS Sheet

Literature and Reviews

Accessing the charge separation effects in dye-sensitized solar cells based on a vectorial planning of supramolecular ruthenium dye, A. Parussulo et al., Inorganica Chim. Acta, 453, 764-770 (2016); DOI: 10.1016/j.ica.2016.09.039.
Artificial photosynthesis based on dye-sensitized nanocrystalline TiO2 solar cells, J.-J. Lagref et al., Inorganica Chim. Acta, 361(3), 735-745(2008); DOI: 10.1016/j.ica.2007.05.061.
Molecular engineering on semiconductor surfaces: design, synthesis and application of new efficient amphiphilic ruthenium photosensitizers for nanocrystalline TiO₂ solar cells, J.-J Lagref et al., Synth. Met., 138(1-2), 333-339(2003); DOI: 10.1016/S0379-6779(03)00034-1.
Cobalt Redox Mediators for Ruthenium-Based Dye-Sensitized Solar Cells: A Combined Impedance Spectroscopy and Near-IR Transmittance Study, Y. Liu et al., J. Phys. Chem. C, 115(38), 18847–18855(2011); DOI: 10.1021/jp204519s.
Highly efficient solid-state dye-sensitized TiO₂ solar cells via control of retardation of recombination using novel donor-antenna dyes, C.S. Karthikeyan et al., Sol. Energy Mater Sol. Cells, 91(5), 432-439(2007); DOI: 10.1016/j.solmat.2006.10.006.
Synthesis and characterization of electrochemiluminescent ruthenium(II) complexes containing o-phenanthroline and various α-diimine ligands, B. Kim et al., 63(3), 595-602(2004); DOI: 10.1016/j.talanta.2003.09.001.

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