460347-59-5

Basic information

• Product Name: (10-Phenyl-9-anthracenyl)boronic acid pinacol ester
• Synonyms: (10-Phenyl-9-anthracenyl)boronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(10-phenyl-9-anthracenyl)-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(9-phenylanthracen-10-yl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(10-Phenylanthracen-9-Yl)-1,3,2-Dioxaborolane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(10-phenyl-9-anthracenyl)-;9-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-10-phenylanthracene
• CAS NO: 460347-59-5
• Molecular Formula: C₂₆H₂₅BO₂
• Molecular Weight: 380.29
• Mol File: 460347-59-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 165.0 to 169.0 °C
• Boiling Point: 524.111 °C at 760 mmHg
• Flash Point: 270.773 °C
• Appearance: /
• Density: 1.15
• CAS DataBase Reference: (10-Phenyl-9-anthracenyl)boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: (10-Phenyl-9-anthracenyl)boronic acid pinacol ester(460347-59-5)
• EPA Substance Registry System: (10-Phenyl-9-anthracenyl)boronic acid pinacol ester(460347-59-5)

Safety Data

• Hazardous Substances Data: 460347-59-5(Hazardous Substances Data)

Usage

Preparation

9-Bromo-10-phenylanthracene (5.8g, 17.4mmol), bis(pinacolato)diboron(6.63 g, 26.1 mmol), Pd(dppf)Cl2 (710 mg, 0.87 mmol), and KOAc (10.23 g, 104.4 mmol) were mixed in a 250mL flask containing 1,4-dioxane (60 mL). The reaction mixture was refluxed for 24h under nitrogen. After it was cooled to room temperature, a dilute hydrochloric acid solution quenched. The mixture was extracted with CH2Cl2 and dried over anhydrous MgSO4. The crude product was concentrated by rotary evaporation and further purified by silica gel column chromatography (CH2Cl2 / petroleum ether (1:1,v/v)) to afford a light yellow powder (4.0 g, 60.4 %). 1H NMR (500 MHz, CDCl3) δ 8.46 (d, J = 8.7 Hz, 2H), 7.65 (d, J = 8.8 Hz, 2H), 7.57 (dq, J = 14.2, 7.0 Hz, 3H), 7.51 – 7.46 (m, 2H), 7.41 (d, J = 7.0 Hz, 2H), 7.34 (dd, J = 8.1, 7.1 Hz, 2H), 1.63 (s, 12H). EI-MS (m/z): Calculated for C26H25BO2: 380.29. Found [M+]: 379.92. Synthesis of 4,4,5,5-Tetramethyl-2-(10-phenylanthracen-9-yl)-1,3,2-dioxaborolane

Upstream product

• 523-27-3 9,10-Dibromoanthracene 
• 108-86-1 bromobenzene 
• 602-55-1 9-phenylanthracene 
• 1564-64-3 9-Bromoanthracene 
• 100622-34-2 anthracene-9-boronic acid 
• 23674-20-6 9-bromo-10-phenylanthracene 
• 73183-34-3 bis(pinacol)diborane 
• 98-80-6 phenylboronic acid 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1198211-88-9 1,3-bis(9-(4-(10-phenylanthracen-9-yl)phenyl)-9H-fluoren-9-yl)benzene 

Relevant articles and documents

ORGANIC LIGHT-EMITTING DEVICE

An organic light-emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, wherein the emission layer includes a polycyclic compound represented by Formula 1 and a host, and wherein an amount of the polycyclic compound is less than an amount of the host in the emission layer, wherein Formula 1 is as provided herein.

Diphenylanthracene Dimers for Triplet-Triplet Annihilation Photon Upconversion: Mechanistic Insights for Intramolecular Pathways and the Importance of Molecular Geometry

Novel approaches to modify the spectral output of the sun have seen a surge in interest recently, with triplet-triplet annihilation driven photon upconversion (TTA-UC) gaining widespread recognition due to its ability to function under low-intensity, noncoherent light. Herein, four diphenylanthracene (DPA) dimers are investigated to explore how the structure of these dimers affects upconversion efficiency. Also, the mechanism responsible for intramolecular upconversion is elucidated. In particular, two models are compared using steady-state and time-resolved simulations of the TTA-UC emission intensities and kinetics. All dimers perform TTA-UC efficiently in the presence of the sensitizer platinum octaethylporphyrin. The meta-coupled dimer 1,3-DPA2 performs best yielding a 21.2% upconversion quantum yield (out of a 50% maximum), which is close to that of the reference monomer DPA (24.0%). Its superior performance compared to the other dimers is primarily ascribed to the longer triplet lifetime of this dimer (4.7 ms), thus reinforcing the importance of this parameter. Comparisons between simulations and experiments reveal that the double-sensitization mechanism is part of the mechanism of intramolecular upconversion and that this additional pathway could be of great significance under specific conditions. The results from this study can thus act as a guide not only in terms of annihilator design but also for the design of future solid-state systems where intramolecular exciton migration is anticipated to play a major role.

Organic blue fluorescent material and preparation method and application thereof

The invention relates to an organic blue fluorescent material and a preparation method and application thereof. The material adopts a delta bond as a bridge chain to connect two anthracene molecule luminescence units and regulate the conjugation state of organic molecules; meanwhile, a steric hindrance group is introduced onto the delta bond to inhibit a pi-pi accumulation effect among the organicmolecules, and correspondingly the organic blue fluorescent material is prepared and has high thermal stability and high luminous quantum efficiency. The specific preparation method and application mainly include the steps of adopting 9-benzanthracene-10 borate and 4,4'-dibromo diphenyl bis-substituted methane for conducting a Suzuki coupling reaction to prepare the organic blue fluorescent material. The material is adopted as a luminous layer and achieves a non-doped deep blue OLED device with high performance.