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(10-Phenylanthracen-9-yl)boronic acid丨CAS 334658-75-2 Best Manufacturer
(10-Phenylanthracen-9-yl)boronic acid (CAS 334658-75-2), also known as 10-phenylanthracene-9-boronic acid, is an aromatic organoboron compound containing an anthracene core, a phenyl substituent at the 10-position, and a boronic acid group at the 9-position. Its extended π-conjugated framework and reactive boronic acid functionality make it a useful intermediate for synthesizing advanced organic electronic materials. The compound is particularly relevant to OLED materials development, organic semiconductor research, and Suzuki–Miyaura cross-coupling chemistry.
Chemical Identifiers
| InChI | 1S/C20H15BO2/c22-21(23)20-17-12-6-4-10-15(17)19(14-8-2-1-3-9-14)16-11-5-7-13-18(16)20/h1-13,22-23H |
| InChI Key | RVPCPPWNSMAZKR-UHFFFAOYSA-N |
| Smiles | OB(C1=C2C=CC=CC2=C(C3=CC=CC=C3)C4=CC=CC=C14)O |
| EC No. | 805-893-8 |
| MDL No. | MFCD11111989 |
| PubChem CID | 22247164 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
The boronic acid group enables (10-Phenylanthracen-9-yl)boronic acid to participate in Suzuki–Miyaura cross-coupling reactions with suitable aryl or heteroaryl halides. Under optimized palladium-catalyzed conditions, these reactions form carbon–carbon bonds and produce substituted anthracene derivatives or extended aromatic structures. This synthetic approach is valuable for preparing OLED intermediates and functionalized polycyclic aromatic compounds. Due to steric effects around the 9-position of anthracene, catalyst selection and reaction conditions may require optimization.
Applications in OLED Materials Development
(10-Phenylanthracen-9-yl)boronic acid is an important building block for synthesizing anthracene-based compounds investigated in organic light-emitting diode (OLED) technology. Anthracene derivatives are widely studied for their fluorescence characteristics and electronic properties, particularly in blue-emitting materials. The phenyl substituent can influence molecular geometry and intermolecular interactions, while the boronic acid group enables the introduction of additional aromatic units. The resulting derivatives may be evaluated as fluorescent emitters, host materials, or other functional OLED components, depending on their molecular structures and measured properties.
Applications in Organic Semiconductor Research
The anthracene framework provides an extended π-electron system relevant to organic semiconductor development. (10-Phenylanthracen-9-yl)boronic acid can be used to synthesize compounds with modified electronic structures and molecular packing characteristics. Researchers may investigate these derivatives for charge-transport behavior, energy-level alignment, thermal properties, and film formation. Such studies support the development of functional materials for organic electronic devices.
Applications in Photophysical and Luminescent Materials
Anthracene-based compounds are widely investigated for their optical properties, including fluorescence and light absorption. (10-Phenylanthracen-9-yl)boronic acid provides a precursor for preparing luminescent molecules with different aromatic substituents. Structural modifications can influence emission wavelength, fluorescence efficiency, and excited-state behavior. The resulting compounds may be studied for applications in fluorescent materials, optical research, and organic optoelectronics.
