950761-81-6

Usage

Uses

Used in Organic Synthesis:
4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane is used as a reactant in organic synthesis for the preparation of complex organic molecules. Its boron-containing structure allows for its use in metal-catalyzed cross-coupling reactions, which are important in the construction of these molecules.
Used in Organic Electronic Materials:
In the field of organic electronics, 4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane is used as a building block for the preparation of materials such as organic light-emitting diodes (OLEDs) and organic photovoltaics. Its unique fluorescent properties make it a valuable component in these applications.
Used in Fluorescent Probes:
4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane is used as a fluorescent probe for tracking biological processes in cells and tissues. Its unique fluorescent properties make it useful for visualizing and studying these processes in various research applications.

Upstream product

• 23683-68-3 3-bromoperylene 
• 73183-34-3 bis(pinacol)diborane 
• 198-55-0 PERYLENE 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 5419-55-6 Triisopropyl borate 
• 955121-20-7 (perylene-3-yl)boronic acid 

Downstream Products

• 1352088-68-6 [10,20-bis-(3,5-di-tert-butylphenyl)-5,15-bis-(perylen-1-yl)-porphyrinato]zinc(II) 
• 1391420-87-3 C₃₆H₂₉N 
• 1425378-71-7 C₄₆H₂₇Cl 
• 1425378-72-8 C₄₆H₂₆ 
• 1435894-83-9 C₂₆H₁₁BrF₄ 
• 1392816-23-7 C₅₄H₃₁Br 

Relevant academic research and scientific papers

Fluorescent perylenylpyridine complexes: an experimental and theoretical study

The perylene derivative 2-(3-perylenyl)-4-methylpyridine (HPerPy) was prepared and used to synthesize [Ag(HPerPy)(PPh3)(OClO3)], with the perylene ligand bonded to the metal centre only by the pyridine nitrogen. The treatment of HPer

An efficient synthesis of quaterrylenedicarboximide NIR dyes

(Chemical Equation Presented) Quaterrylenedicarboximides were prepared from 9-bromoperylene-3,4-dicarboximides by palladium-catalyzed coupling with 3-perylene boronic ester, followed by oxidative cyclodehydrogenation of the resulting perylene-perylenedica

Sodium-Promoted Borylation of Polycyclic Aromatic Hydrocarbons

Sodium dispersion promotes the reductive borylation of polycyclic aromatic hydrocarbons (PAHs) with MeOBpin. Anthracenes and phenanthrenes are converted to the corresponding dearomatized diborylated products. The reductive diborylation of naphthalene-based small π-systems yields similar yet unstable products that are oxidized into formal C-H borylation products with unique regioselectivity. Pyrene is converted to 1-borylpyrene without the addition of an oxidant. The latter two reactions represent a new route to useful borylated PAHs that rivals C-X borylation and catalytic C-H borylation.

Communication of Bichromophore Emission upon Aggregation – Aroyl-S,N-ketene Acetals as Multifunctional Sensor Merocyanines

Aroyl-S,N-ketene acetal-based bichromophores can be readily synthesized in a consecutive three-component synthesis in good to excellent yields by condensation of aroyl chlorides and an N-(p-bromobenzyl) 2-methyl benzothiazolium salt followed by a Suzuki coupling, yielding a library of 31 bichromophoric fluorophores with substitution pattern-tunable emission properties. Varying both chromophores enables different communication pathways between the chromophores, exploiting aggregation-induced emission (AIE) and energy transfer (ET) properties, and thus, furnishing aggregation-based fluorescence switches. Possible applications range from fluorometric analysis of alcoholic beverages to pH sensors.

Compound containing perylene and fluorobenzene as well as preparation method and application of compound

The invention discloses a compound containing perylene and fluorobenzene. The structure of the compound is shown as a formula 1, the preparation method of the compound comprises the following specificsteps: (1) reacting perylene with N-bromo succinimide to prepare a compound I; (2) reacting the compound I with bis (pinacolato) diboron to obtain a compound II; (3) reacting the compound II with 2,3, 5, 6-tetrafluoro-1, 4-dibromobenzene to prepare a compound III; and (4) reacting the compound III with pentafluorophenylboronic acid to obtain a compound IV. Based on good structural modification and various photoelectric properties of perylene and perylene series compounds, high-color-purity green-light LED devices can be prepared, and huge application potential in the aspect of green fluorescent powder for white-light LEDs is achieved.

Efficient Triplet–Triplet Annihilation Upconversion in Solution and Hydrogel Enabled by an S-T Absorption Os(II) Complex Dyad with an Elongated Triplet Lifetime

A new Os(II) complex dyad featuring direct singlet-to-triplet (S-T) absorption and intramolecular triplet energy transfer (ITET) with lifetime up to 7.0 μs was designed to enhance triplet energy transfer efficiency during triplet–triplet annihilation upconversion (TTA-UC). By pairing with 9,10-bis(phenylethynyl)anthracene (BPEA) as a triplet acceptor, intense upconverted green emission in deaerated solution was observed with unprecedented TTA-UC emission efficiency up to 26.3% (with a theoretical maximum efficiency of 100%) under photoexcitation in the first biological transparency window (650–900 nm). Meanwhile, a 7.1% TTA-UC emission efficiency was acquired in an air-saturated hydrogel containing the photosensitizer and a newly designed hydrophilic BPEA derivative. This ITET mechanism would inspire further development of a highly efficient TTA-UC system for biological fields and renewable energy production.

Intersystem crossing: via charge recombination in a perylene-naphthalimide compact electron donor/acceptor dyad

In order to study the relationship between the molecular structures of compact electron donor/acceptor dyads and the spin-orbit charge transfer intersystem crossing (SOCT-ISC) efficiency, we prepared a perylene (Pery)-naphthalimide (NI) dyad, in which the Pery unit is the electron donor and the NI unit is the electron acceptor, where the two units adopt an almost orthogonal geometry. The photophysical properties of the dyad were studied with steady state and femtosecond/nanosecond transient absorption (fs TA and ns TA) spectroscopies, time resolved electron paramagnetic resonance (TREPR) spectroscopy and DFT computations. A very weak charge transfer (CT) absorption band was observed, but the fluorescence of the Pery unit is strongly quenched. Upon selective excitation into the NI unit, the fast intramolecular CS process (10 ps) occurs, followed by ISC and only the 3Pery? state is observed; whereas upon selective photoexcitation into the perylene unit, an ultrafast charge separation (0.66 ps) is observed, followed by SOCT-ISC (8 ns) to populate the 3Pery? state. Moreover, the perylene radical cation is also observed on the ns timescale, presumably formed by intermolecular charge transfer. The lifetime of the 3Pery triplet state was determined to be τT = 214 μs with ns TA spectroscopy. The singlet oxygen quantum yield was measured as ΦΔ = 80%, although the potential energy curve of the torsion between the donor and acceptor is shallow. The SOCT-ISC mechanism was confirmed by TREPR spectroscopy. The dyad was used as a triplet photosensitizer for the generation of delayed fluorescence (luminescence lifetime τDF = 57.3 μs). This journal is

Spin–Orbit Charge-Transfer Intersystem Crossing (ISC) in Compact Electron Donor–Acceptor Dyads: ISC Mechanism and Application as Novel and Potent Photodynamic Therapy Reagents

Spin–orbit charge-transfer intersystem crossing (SOCT-ISC) is useful for the preparation of heavy atom-free triplet photosensitisers (PSs). Herein, a series of perylene-Bodipy compact electron donor/acceptor dyads showing efficient SOCT-ISC is prepared. T

Ni-Catalyzed α-Selective C-H Borylations of Naphthalene-Based Aromatic Compounds

The ability of α-borylated naphthalene-based aromatic compounds is important because it provides ready access to interesting novel extended π-systems. In this report, we disclose the Ni-catalyzed α-selective C-H borylations of naphthalene-based aromatic c

Spin-Allowed Transitions Control the Formation of Triplet Excited States in Orthogonal Donor-Acceptor Dyads

Reliance on triplet excited states (triplets) of molecules with heavy atoms, such as precious metals, limits their potential in technological applications. We envision that triplets of π-conjugated organic molecules could play bigger roles; however, their production without heavy atoms remains challenging. The direct, spin-forbidden conversion of singlet charge-separated states to triplets in an electron donor-acceptor (D-A) pair is a promising approach. Here, using a series of orthogonal D-A type boron dipyrromethene (BODIPY) derivatives as a model system, we show that the formation of triplets is largely controlled by the spin-allowed transitions. Yet, this spin-forbidden process can still proceed much faster than ordinary intersystem crossing between (π π*) states under favorable conditions because of stronger spin-orbit coupling. Our findings reveal a clear physical basis for this spin-forbidden process and provide guidelines for future molecular designs exploiting the process. Production of triplet excited states of π-conjugated organic molecules in high yields without using heavy atoms remains challenging. The direct formation of triplet excited states from singlet charge-separated states is a promising approach. Here, we show that spin-allowed electron-transfer reactions largely control such a formation, yet the spin-forbidden transition can outcompete the spin-allowed transitions under favorable conditions because of stronger spin-orbit coupling. Triplet excited states (triplets) serve as key intermediates in critical technologies and processes ranging from organic synthesis to biomedicine to molecular electronics. Production of triplets of π-conjugated organic molecules without heavy atoms remains challenging. Spin-orbit, charge-transfer intersystem crossing (SOCT-ISC) directly converts singlet charge-separated states to triplets in an electron donor-acceptor (D-A) pair. Here, using a series of orthogonal D-A type boron dipyrromethene (BODIPY) derivatives as a model system, we show that the formation of triplets is largely controlled by the spin-allowed transitions rather than by SOCT-ISC. Yet, the SOCT-ISC process can still proceed much faster than ordinary ISC between (π π*) states because the spin-orbit coupling of SOCT-ISC is 2 orders of magnitude stronger. We further show that such a process can produce triplets in a non-triplet-forming molecule, perylene. Our findings reveal a clear physical basis for this spin-forbidden process and provide guidelines for future molecular designs exploiting the process.