2,2'-(1,2-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
CAS Number 269410-07-3
Boronates, Chemistry Building Blocks, COF Ligands, Monomers, Non-Heterocyclic Building Blocks, Porous Organic Frameworks
Covalent Organic Frameworks (COFs) Phenylene Ligand
as an ortho-functionalized building block for polyaromatic hydrocarbons and photoluminescent materials
Overview | Product Information | MSDS | Related Products
2,2'-(1,2-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (CAS number 269410-07-3) is a benzene building block substituted with two boronic acid esters at the ortho-position. The pinacolborane (Bpin) groups enable the coupling reaction at the ortho-position of the building block, through the Suzuki reaction. The ortho molecular geometry impacts the performance on the materials. For instance, an anthracene dimer linked by 2,2'-(1,2-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) exhibits a fast charge separation rate (8 ps) due to its strong electronic coupling and large charge separation driving force.
2,2'-(1,2-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) is also used for the synthesis of rigid ligands in photoluminescent complexes. The ortho branching of the ligand provides an ideal geometry for the chelation to metal centres. The resulting Pt complex has shown an external quantum efficiency of 8% at 100 cd/m2.
MOF and COF Ligands
Phenylene ligand for cross-linked networks
Facile Reactions
Bpin possesses excellent reactivity
High Purity
>98% pure
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General Information
| CAS Number | 269410-07-3 |
|---|---|
| Chemical Formula | C18H28B2O4 |
| Full Name | 2,2'-(1,2-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) |
| Molecular Weight | 330.04 g/mol |
| Synonyms | 1,2-Benzenediboronic acid bis(pinacol) ester, 1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene |
| Classification or Family | Porous organic frameworks, COFs, Phenylene building blocks, Photoluminescence |
Chemical Structure
Product Details
| Purity | > 98% |
|---|---|
| Melting Point | 116 °C |
| Appearance | White to off-white powder |
MSDS Documentation
2,2'-(1,2-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) MSDS Sheet
References
- Blue phosphorescent platinum(II) complexes based on tetradentate ligand with rigid and highly distorted linkage for efficient organic light-emitting diodes, J. Kang et al., Dyes Pigm., 207, 110770 (2022); DOI: 10.1016/j.dyepig.2022.110770.
- Symmetry-breaking charge separation in weakly coupled anthracene dimers,, L. Lv et al., J. Mater. Chem. C, 11, 16782–16791 (2023); DOI: 10.1039/D3TC03007E.
- Construction of a tetrabenzotetrathia[8]circulene by a “fold-in” oxidative fusion reaction: synthesis and optical properties, S. Gu et al., Chem. Commun., 60, 6264–6267 (2024); DOI: 10.1039/D4CC01598C.
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