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Ordering 10-(2-Naphthyl)anthracene-9-boronic Acid丨CAS 597554-03-5
10-(2-Naphthyl)anthracene-9-boronic acid (CAS 597554-03-5), also known as 10-(naphthalen-2-yl)anthracene-9-boronic acid, is a polycyclic aromatic organoboron compound featuring an anthracene framework substituted with a naphthyl group at the 10-position and a boronic acid group at the 9-position. The compound combines the extended π-conjugated structure of anthracene, the aromatic characteristics of naphthalene, and the synthetic versatility of a boronic acid functionality. Anthracene-based compounds are widely investigated in organic electronic materials because of their optical and electronic properties, particularly in luminescent molecular systems. The boronic acid group enables further structural modification through suitable cross-coupling reactions, making this compound a useful intermediate for OLED materials development, organic semiconductor research, photophysical studies, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C24H17BO2/c26-25(27)24-21-11-5-3-9-19(21)23(20-10-4-6-12-22(20)24)18-14-13-16-7-1-2-8-17(16)15-18/h1-15,26-27H |
| InChI Key | YGVDBZMVEURVOW-UHFFFAOYSA-N |
| Smiles | OB(O)C1=C2C=CC=CC2=C(C2=CC3=C(C=CC=C3)C=C2)C2=C1C=CC=C2 |
| EC No. | 808-164-2 |
| MDL No. | MFCD11973625 |
| PubChem CID | 23088556 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
The boronic acid functionality of 10-(2-Naphthyl)anthracene-9-boronic acid enables its use in Suzuki–Miyaura cross-coupling reactions. Under appropriately optimized palladium-catalyzed conditions, the compound can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation provides a route for introducing a naphthyl-substituted anthracene fragment into larger aromatic frameworks. It is particularly useful for preparing functionalized anthracene derivatives, extended polycyclic aromatic compounds, and advanced organic electronic materials intermediates. Because the boronic acid group is located at the sterically influenced 9-position of anthracene, reaction conditions may require optimization to achieve satisfactory coupling efficiency.
Applications in OLED Materials Research
10-(2-Naphthyl)anthracene-9-boronic acid is particularly relevant to the synthesis of organic compounds investigated in organic light-emitting diode (OLED) technology. Anthracene-containing structures are important in OLED materials research because their extended aromatic frameworks can provide useful fluorescence characteristics and support the development of specialized emissive materials. The naphthyl substituent at the 10-position introduces an additional aromatic fragment that may influence molecular geometry, intermolecular interactions, and solid-state behavior. Through suitable coupling reactions at the boronic acid functionality, researchers can prepare more complex anthracene derivatives for evaluating their potential as emissive materials, host materials, or other functional OLED components.
Applications in Blue OLED Materials Development
Anthracene-based molecular structures are frequently investigated in the development of blue-emitting organic materials. Their aromatic frameworks can support fluorescence, while appropriate substitution allows researchers to modify electronic characteristics, molecular packing, and photophysical behavior. 10-(2-Naphthyl)anthracene-9-boronic acid provides a useful intermediate for constructing substituted anthracene derivatives containing additional aromatic or heteroaromatic units. The naphthyl group and the 9-position boronic acid functionality offer opportunities for systematic molecular modification. Researchers may evaluate the resulting compounds for emission wavelength, photoluminescence efficiency, thermal characteristics, and device performance. Blue emission and practical device suitability must be established experimentally for each final compound.
Applications in Organic Semiconductor Research
10-(2-Naphthyl)anthracene-9-boronic acid may support the development of organic semiconductor compounds containing extended polycyclic aromatic structures. Anthracene and naphthalene units provide π-electron systems that can influence electronic interactions and molecular organization when incorporated into appropriately designed materials. Researchers may use this compound to synthesize candidate molecules for investigating charge transport, energy-level alignment, molecular packing, and solid-state electronic behavior. By connecting the substituted anthracene framework with selected aromatic or heteroaromatic fragments, different molecular architectures can be developed for systematic semiconductor materials research.
