2,2'-(1,2-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane), CAS 269410-07-3, also known as 1,2-benzenediboronic acid bis(pinacol) ester, is a benzene building block carrying two pinacolborane (Bpin) groups in the ortho position. Supplied by Ossila at >98% purity as a white to off-white powder, it serves as a phenylene ligand for covalent organic frameworks (COFs), polyaromatic hydrocarbons and photoluminescent materials.
The two Bpin groups are highly reactive in Suzuki coupling, allowing new bonds to be formed at adjacent ring positions. This ortho geometry shapes the behaviour of the final material: an anthracene dimer joined through this linker shows a fast charge separation rate (8 ps), attributed to strong electronic coupling and a large driving force for charge separation.
The ortho branching also makes the compound suited to building rigid ligands that chelate metal centres. A Pt complex prepared this way has reached an external quantum efficiency of 8% at 100 cd/m2.
- Suzuki coupling at the ortho position of a benzene core.
- Synthesis of ligands and linkers for covalent organic frameworks and other porous cross-linked networks.
- Construction of polyaromatic hydrocarbons, including ortho-linked anthracene dimers for charge separation studies.
- Preparation of rigid chelating ligands for photoluminescent metal complexes such as Pt emitters for OLEDs.
| Brand | Ossila |
|---|---|
| CAS number | 269410-07-3 |
| Molecular formula | C18H28B2O4 |
| Purity | > 98% |
| Category | — |
| Pack sizes | 250 mg, 500 mg, 1 g |
| Physical form | White to off-white powder |
| Storage | — |
- Product code: B4141
- 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: Porous organic frameworks, COFs, Phenylene building blocks, Photoluminescence
- Melting Point: 116 °C
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