4-(Diphenylamino)phenylboronic Acid | CAS 201802-67-7 | ≥98%

Organic light-emitting diode (OLED) materials: 4-(Diphenylamino)phenylboronic acid is a key building block for the synthesis of electroluminescent materials used in organic light-emitting diodes. The triphenylamine unit imparts excellent hole-transporting ability to the resulting polymers and small molecules. It has been used as an end-capping agent for polyfluorene-based conjugated polymers, where it improves thermal stability (increased Tg and Td) and luminescence efficiency by reducing interchain emissive species and suppressing exciton self-quenching. These end-capped polymers are used as emissive layers in polymer light-emitting diodes (PLEDs) for blue and white emission.

Dye-sensitised solar cells (DSSCs): This compound serves as a Suzuki coupling partner for introducing the triphenylamine donor unit into donor–π–acceptor (D–π–A) organic sensitiser architectures for dye-sensitised solar cells. The triphenylamine moiety is selected as an electron donor because of its propeller-like nonplanar conformation, which suppresses dye aggregation on the TiO₂ surface, and its strong electron-donating character, which promotes intramolecular charge transfer. It has been used in the synthesis of D–A–D conjugated systems based on dibenzosuberenone, achieving power conversion efficiencies of ~2.5%.

Suzuki–Miyaura cross-coupling reactions: As an arylboronic acid, 4-(diphenylamino)phenylboronic acid participates in palladium-catalysed Suzuki–Miyaura cross-coupling reactions with aryl and heteroaryl halides. The diphenylamino group is electron-donating, which influences the reactivity of the boronic acid and the electronic properties of the resulting biaryl products. This makes it a versatile reagent for constructing extended conjugated systems, p-quaterphenyls, and other architectures for optoelectronic applications.

Solid-state blue emitters: Sigma-Aldrich lists this compound specifically for the synthesis of p-quaterphenyls laterally substituted with dimesitylboryl groups for use as solid-state blue emitters. These materials are of interest for display technologies requiring efficient blue fluorescence in the solid state.

Conjugated polymer synthesis: The compound is used as a monomer or end-capper in Suzuki polycondensation reactions to prepare conjugated polymers incorporating triphenylamine units. These polymers exhibit p-type semiconducting behaviour dominated by hole transport, and are investigated as active layers in OLEDs, organic field-effect transistors (OFETs), and organic photovoltaics (OPVs).

Perylene dye functionalisation: 4-(Diphenylamino)phenylboronic acid has been employed in the synthesis of perylene dyes bearing multiple triphenylamine substituents, extending the absorption spectrum and improving charge separation properties for photovoltaic and photophysical studies.