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Top Selected Triphenylen-2-ylboronic acid丨CAS 654664-63-8
Triphenylen-2-ylboronic acid (CAS 654664-63-8), also known as triphenylene-2-boronic acid, is an aromatic organoboron compound featuring a boronic acid group at the 2-position of a triphenylene framework. Triphenylene is a rigid, planar polycyclic aromatic hydrocarbon composed of four fused benzene rings. Its extended π-conjugated structure and molecular rigidity make it an important structural unit in organic electronic materials and advanced aromatic chemistry. By combining this polycyclic framework with a reactive boronic acid functionality, Triphenylen-2-ylboronic acid provides a versatile building block for synthesizing complex aromatic compounds. It is particularly relevant to OLED materials research, organic semiconductor development, Suzuki–Miyaura cross-coupling reactions, and specialty organic synthesis.
Chemical Identifiers
| InChI | InChI=1S/C18H13BO2/c20-19(21)12-9-10-17-15-7-2-1-5-13(15)14-6-3-4-8-16(14)18(17)11-12/h1-11,20-21H |
| InChI Key | PXFBSZZEOWJJNL-UHFFFAOYSA-N |
| Smiles | B(C1=CC2=C(C=C1)C3=CC=CC=C3C4=CC=CC=C42)(O)O |
| EC No. | 1533716-785-6 |
| MDL No. | MFCD16660186 |
| PubChem CID | 59805119 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
The boronic acid group of Triphenylen-2-ylboronic acid enables its use in Suzuki–Miyaura cross-coupling reactions. Under appropriate palladium-catalyzed conditions, it can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation provides a practical route for introducing a triphenylen-2-yl fragment into complex aromatic frameworks. The reaction is especially valuable for preparing extended π-conjugated molecules, substituted polycyclic aromatic compounds, and functional organic intermediates. Because triphenylene derivatives may exhibit limited solubility in certain solvents, reaction conditions may require optimization to achieve satisfactory conversion and product isolation.
Applications in OLED Materials Research
Triphenylen-2-ylboronic acid is a useful intermediate for preparing organic compounds investigated in organic light-emitting diode (OLED) technology. Triphenylene-containing structures are widely explored in the design of host materials and other functional organic electronic components because their rigid aromatic frameworks can contribute to thermal and morphological characteristics. Through suitable coupling reactions, this compound can be incorporated into larger molecular architectures containing additional aromatic or heteroaromatic units. Researchers may use the resulting compounds to investigate energy-level alignment, charge-transport behavior, photophysical properties, and device stability. The suitability of each derivative for a specific OLED function depends on its complete molecular structure and measured performance.
Applications in Organic Semiconductor Research
Triphenylen-2-ylboronic acid may support the synthesis of organic semiconductor materials containing rigid polycyclic aromatic units. The triphenylene framework offers an extended π-electron system that can influence molecular packing and electronic interactions in appropriately designed compounds. Researchers may use this building block to prepare candidate materials for investigating charge transport, molecular organization, energy levels, and solid-state behavior. By connecting triphenylene with selected aromatic or heteroaromatic fragments, different molecular structures can be developed for systematic evaluation. Potential applications include exploratory research involving organic electronic devices and other functional semiconductor systems.
Applications in Liquid Crystal Materials Research
Triphenylene-based molecular structures are also relevant to discotic liquid crystal research. The planar aromatic core can support the design of disc-shaped molecules that, when appropriately substituted, may exhibit columnar molecular organization. Triphenylen-2-ylboronic acid provides a synthetic route for introducing additional aromatic fragments or functional groups into triphenylene-containing structures. Researchers can investigate how molecular substitution influences self-assembly, phase behavior, thermal transitions, and intermolecular interactions. The presence of a triphenylene core alone does not guarantee liquid crystalline behavior, which depends on the overall molecular architecture and substituent design.
