Spiro[fluorene-9,9'-xanthen]-4-ylboronic acid CAS No. 2244281-69-2

Product Description

Spiro[fluorene-9,9'-xanthene]-4-ylboronic acid is a complex organic compound with a unique spirocyclic structure consisting of a fluorene and xanthene ring system with a boronic acid group attached at the 4-position. It is highly valuable in organic synthesis due to its potential in cross-coupling reactions, such as the Suzuki-Miyaura coupling reaction, to form new carbon-carbon or carbon-heteroatom bonds. Its spirocyclic structure and aromatic ring enhance its stability and reactivity, making it a key component in the development of organic light-emitting diodes (OLEDs) and other optoelectronic materials. Furthermore, it is being explored as a hole transport material in perovskite solar cells and for sensor technologies with selective binding and fluorescence responses. Handling and storage of this compound require inert conditions to prevent decomposition, and its synthesis involves multiple steps, including cyclization and boronate ester formation.

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Product Use & Characteristics

Properties

• Molecular Formula: C₂₅H₁₇BO₃

• Molecular Weight: 376.2 g/mol

• Structure: Contains a spiro[fluorene-9,9'-xanthene] core with a boronic acid group (-B(OH)₂) attached at the 4-position.

• Appearance: Yellow powder

• Hazard Classification: Warning (GHS); causes skin irritation (H315), eye irritation (H319), and harmful if swallowed (H302).

• Storage: Requires cold-chain transportation for stability and should be stored in a tightly sealed container under an inert atmosphere to maintain its stability and reactivity.

Uses

• Organic Synthesis: Key building block in Suzuki-Miyaura cross-coupling reactions, where the boronic acid group reacts with aryl halides or triflates to form carbon-carbon bonds.

• Organic Light-Emitting Diodes (OLEDs): Serves as a hole-transporting material (HTM) or host material due to its excellent charge mobility and stability, used in diode-type UV photodetectors and electroluminescent devices.

• Photovoltaics: Employed in the design of HTMs for perovskite solar cells, enhancing device efficiency and longevity.

• Polymerization: Facilitates the synthesis of spiro[fluorene-9,9'-xanthene]-based polymers via Suzuki coupling for advanced materials.

• Fluorescent Materials: Serves as a precursor for high-brightness dyes and sensors.

• Coordination Chemistry: May serve as a ligand or intermediate in coordination chemistry.

Synthesis Methods

• Core Scaffold Synthesis: The spiro[fluorene-9,9'-xanthene] core can be synthesized via one-pot methods, such as acid-catalyzed condensation of fluorenone with phenols (e.g., using methanesulfonic acid).

• Boronate Formation: The boronic acid group can be introduced at the 4-position by borylation of the corresponding 4-bromo-spiro[fluorene-9,9'-xanthene] precursor using bis(pinacolato)diboron in the presence of a palladium catalyst (e.g., Pd(dppf)Cl₂) and base (e.g., potassium acetate), followed by hydrolysis to the free boronic acid.

• Further Derivatization: Modified Ullmann reactions or cross-coupling can be used for further functionalization and derivatization.

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