5,5'-Bis(trifluoromethyl)-2,2'-bipyridine
CAS Number 142946-80-3
Chemistry Building Blocks, Fluorinated Building Blocks, Heterocyclic Building Blocks, Materials, Monomers
An electron withdrawing bipyridyl ligand
Used as a chelating ligand for the preparation of Ir(III) photocatalysts
Specifications | MSDS | Literature and Reviews
5,5′-Bis(trifluoromethyl)-2,2′-bipyridine (5,5′-dCF3bpy), CAS number 142946-80-3, is a bipyridyl ligand with two electron withdrawing trifluoromethyl groups at 5,5'-positions on the conjugated bipyridyl rings. It is normally used as a chelating ligand for the preparation of the well-established [Ir(dFCF3ppy)2 (5,5′-dCF3bpy)]PF6 and other Ir(III) photocatalysts. [Ir(dFCF3ppy)2-(5,5′-dCF3bpy)]PF6 is a cyclometalated iridium(III) complex that are widely used in visible-light mediated photocatalytic organic transformations including the alkylation of remote C-H bonds and alkene aminoarylation.
Yellow light emitting cyclometalated iridium(III) complexes coordinated with ligand 5,5′-bis(trifluoromethyl)-2,2′-bipyridine, [Ir(Hppy)2(dCF3bpy)]PF6 and [Ir(HF2ppy)2(dCF3bpy)]PF6, show relative long lifetimes at room temperature owing to the phosphorescence derived from the mixed metal-ligand-to-ligand charge transfer (MLLCT) excited states. The system engaging the photosensitizers, K2PtCl4, and triethylamine showed highly efficient H2 evolution activities. The turnover numbers (TONs) of H2 evolution based on [Ir(Hppy)2(dCF3bpy)]PF6 and [Ir(HF2ppy)2(dCF3bpy)]PF6 at 96 h of irradiation were reached at 758 and 832 TONs, respectively.
Multiple functional groups
For facile synthesis
Fluorinated bipyridine building block
For semiconductors, dyes, and solar cells
Worldwide shipping
Quick and reliable shipping
High purity
>98% High purity
General Information
| CAS Number | 142946-80-3 |
| Chemical Formula | C12H6F6N2 |
| Full Name | 5,5'-Bis(trifluoromethyl)-2,2'-bipyridine |
| Molecular Weight | 292.18 g/mol |
| Synonyms | 5,5′-dCF3bpy, 5,5'-BTFMB, 5,5'-Bis(trifluoromethyl)-2,2'-bipyridyl |
| Classification / Family | Bipyridyl derivatives, Heterocyclic building blocks, Semiconductor synthesis intermediates, Dye-sensitized solar cells (DSSCs) |
Chemical Structure
Product Details
| Purity | >98% (1H NMR) |
| Melting Point | 131 °C |
| Appearance | White to off-white powder/crystals |
MSDS Documentation
5,5'-Bis(trifluoromethyl)-2,2'-bipyridine MSDS Sheet
Literature and Reviews
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Photophysical properties and photosensitizing abilities for hydrogen evolution reactions of robust cyclometalated iridium(III) complexes with 5,5′-bis(trifluoromethyl)-2,2′-bipyridine, N. Yano et al., J. Photochem. Photobiol. A: Chem., 400, 112716 (2020); 10.1016/j.jphotochem.2020.112716.
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Modified Ullmann coupling of 2-chloro-3-trifluoromethylpyridine, S. Munavalli et al., J. Fluor. Chem., 73 (1), 1-6 (1995); DOI: 10.1016/0022-1139(94)03168-Y.
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Trifluoromethyl-substituted 2,2'-bipyridine ligands. Synthetic control of excited-state properties of ruthenium(II) tris-chelate complexes, M. Furue at al., Inorg. Chem., 31 (18), 3792–3795 (1992); DOI: 10.1021/ic00044a022.