201802-67-7

Basic information

• Product Name: 4-(Diphenylamino)phenylboronic acid
• Synonyms: 4-(DIPHENYLAMINO)PHENYLBORONIC ACID, (CONTAINS VARYING AMOUNTS OF ANHYDRIDE),97.0%(T);4-(Diphenylamino)phenylboronic acid;4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride);Triphenylamine-4-boronic Acid;4-Diphenylamino-phenylboronic acid or Triphenylami;4-(Diphenylamino)phe;4-(DiphenylaMino)benzeneboronic acid, 98%;Boronic acid, B-[4-(diphenylaMino)phenyl]- Boronic acid, [4-(diphenylaMino)phenyl]- (9CI)
• CAS NO: 201802-67-7
• Molecular Formula: C₁₈H₁₆BNO₂
• Molecular Weight: 289.14
• Product Categories: blocks;BoronicAcids;B (Classes of Boron Compounds);Boronic Acids;Triphenylamine series;white crystal powder;Phenylamine Series;Aryl;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 201802-67-7.mol
• Article Data: 71

Chemical Properties

• Melting Point: 110-115 °C
• Boiling Point: 484.52 °C at 760 mmHg
• Flash Point: 246.829 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.665
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• PKA: 8.71±0.17(Predicted)
• CAS DataBase Reference: 4-(Diphenylamino)phenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Diphenylamino)phenylboronic acid(201802-67-7)
• EPA Substance Registry System: 4-(Diphenylamino)phenylboronic acid(201802-67-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 201802-67-7(Hazardous Substances Data)

Usage

Description

4-(Diphenylamino)phenylboronic acid is an organic compound that features a boron atom bonded to a phenyl ring with a diphenylamino group attached to the 4-position. It is known for its strong multiphoton-excited blue photoluminescence and lasing properties, making it a valuable material in the field of organic electronics and photonics.

Uses

Used in Organic Electronics Industry:
4-(Diphenylamino)phenylboronic acid is used as a reagent for the preparation of push-pull arylvinyldiazine chromophores and benzothiadiazole-based fluorophores containing triphenylamine functionality. These chromophores and fluorophores are essential for developing blue light-emitting and hole-transporting materials for electroluminescent devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells.
Used in Dye-Sensitized Solar Cells:
4-(Diphenylamino)phenylboronic acid serves as an efficient sensitizer for dye-sensitized solar cells, enhancing their energy conversion efficiency and performance.
Used in Organic Synthesis:
4-(Diphenylamino)phenylboronic acid is utilized as a reagent in Suzuki coupling reactions, a widely used method for the formation of carbon-carbon bonds in organic synthesis. It is particularly useful in ligand-free Suzuki reactions, simplifying the process and reducing the need for additional ligands.
Used in the Production of Advanced Materials:
4-(Diphenylamino)phenylboronic acid is used in the synthesis of p-quaterphenyls laterally substituted with a dimesitylboryl group. These materials are employed as solid-state blue emitters, contributing to the development of next-generation eep-blue organic light-emitting devices (OLEDs) and Prange electroluminescent materials for single-layer white polymer OLEDs.
Chemical Properties:
4-(Diphenylamino)phenylboronic acid is a white to light green solid, indicating its stability and purity as a chemical compound.

InChI:InChI=1/C18H16BNO2/c21-19(22)15-11-13-18(14-12-15)20(16-7-3-1-4-8-16)17-9-5-2-6-10-17/h1-14,21-22H

Upstream product

• 36809-26-4 4-N,N-diphenylamino-1-bromobenzene 
• 121-43-7 Trimethyl borate 
• 589-87-7 1,4-bromoiodobenzene 
• 122-39-4 diphenylamine 
• 1019056-21-3 dimethyl 4-(diphenylamino)phenylboronate 
• 1191417-83-0 C₂₄H₂₈BNO₂ 
• 106-40-1 4-bromo-aniline 
• 603-34-9 N,N-diphenylaminobenzene 
• 106-37-6 1.4-dibromobenzene 
• 7647-01-0 hydrogenchloride 
• 5419-55-6 Triisopropyl borate 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 150-46-9 triethyl borate 
• 7732-18-5 water 

Downstream Products

• 515822-78-3 4,4’-(1,10-phenanthroline-3,8-diyl)bis(N,N-diphenylaniline) 
• 875314-58-2 4-bromo-7-(N,N-diphenylamino)phenyl-(2,1,3)-benzoselenadiazole 
• 830325-93-4 (4-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-N,N-diphenyl-aniline) 
• 167218-30-6 N-(4'-anilino[1,1'-biphenyl]-4-yl)-N,N-diphenylamine 
• 830325-94-5 4-(7-(4-(diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol-4-yl)benzaldehyde 

Relevant articles and documents

A single 2-(2′-hydroxyphenyl)benzothiazole derivative can achieve pure white-light emission

The synthesis and photophysics of two novel 2-(2′-hydroxyphenyl)- benzothiazole (HBT) derivatives are presented. The electron-withdrawing trifluoromethyl (CF3) group in compound 1 facilitates the deprotonation of the phenolic hydroxy group. Well-resolved triple fluorescence from the enol, keto, and phenolic anion, which ranges from 350 to 600 nm, was detected for 1 in ethanol, which marks the first time triple fluorescence from an excited-state intramolecular proton transfer (ESIPT) molecule has been reported. Both triphenylamine and CF3 were introduced into derivative 2. Intramolecular charge transfer and the "red-edge effect" resulted in the bathochromic shift of dual fluorescence of 2. Triple fluorescence was also observed for 2 in ethanol. In mixed acetonitrile and ethanol, pure white-light emission with CIE coordinates of (0.33, 0.33) and a quantum yield of 0.25 was achieved for 2. This work provides a new avenue for the rational design of an ESIPT molecule to achieve white-light generation under mild conditions.

Synergy between twisted conformation and effective intermolecular interactions: Strategy for efficient mechanochromic luminogens with high contrast

A strategy towards efficient mechanochromic luminogens with high contrast is developed. The twisted propeller-like conformations and effective intermolecular interactions not only endow the luminogens with AIE characteristics and high efficiency in the crystalline state, but also render them to undergo conformational planarization and disruption in intermolecular interactions upon mechanical stimuli, resulting in remarkable changes in emission wavelength and efficiency. Copyright

Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption

Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.

1,2,4-thiadiazole compound, preparation method and application thereof

The invention discloses a 1,2,4-thiadiazole compound, a preparation method and an application thereof. The 1,2,4-thiadiazole compound used as a light emitting layer material of an OLED device is capable of obviously promoting the performances of the device, such as luminous intensity, current efficiency, power efficiency, external quantum efficiency and chroma and is capable of prolonging the service life of the device.