5550-08-3

Usage

Uses

Used in Organic Light-Emitting Diodes (OLEDs):
5,5-diphenyl-5H-dibenzo[b,d]silole is utilized as a luminescent material in the development of OLEDs due to its ability to emit light efficiently. This application is particularly beneficial for creating high-quality displays and lighting systems.
Used in Organic Photovoltaics (OPVs):
In the field of organic photovoltaics, 5,5-diphenyl-5H-dibenzo[b,d]silole serves as a key component for enhancing the performance of solar cells. Its incorporation into OPVs can improve the conversion efficiency and overall energy output.
Used in Sensor Industry:
5,5-diphenyl-5H-dibenzo[b,d]silole is employed as a component in the development of sensors, capitalizing on its tunable electronic and optical properties. This allows for the creation of highly sensitive and selective sensors for various applications.
Used as Fluorescent Probes:
In the realm of fluorescent probes, 5,5-diphenyl-5H-dibenzo[b,d]silole is used for its luminescent characteristics, enabling researchers to track and visualize specific biological processes or detect certain molecules with high precision.
Used in Optoelectronic Devices:
5,5-diphenyl-5H-dibenzo[b,d]silole is also utilized in the development of optoelectronic devices, where its electronic and optical properties can be tailored to suit specific requirements, leading to advancements in communication, computing, and imaging technologies.
Overall, 5,5-diphenyl-5H-dibenzo[b,d]silole is a versatile compound with a wide range of applications across various industries, primarily due to its unique structure and luminescent properties.

Upstream product

• 18030-58-5 9,9-dichloro-9-silafluorene 
• 591-51-5 phenyllithium 
• 18766-52-4 5-chloro-5-phenyldibenzosilole 
• 80-10-4 diphenylsilyl dichloride 
• 16291-32-0 biphenyl-2,2'-diyl-bis-lithium 
• 80073-04-7 1-methyl-1-(trimethylsilyl)dibenzosilole 
• 13029-09-9 2,2'-dibromobiphenyl 
• 1116155-57-7 2-(triphenylsilyl)phenyl trifluoromethanesulfonate 
• 775-12-2 diphenylsilane 
• 2236-52-4 2,2'-diiodobiphenyl 
• 2052-07-5 2-Bromobiphenyl 
• 1631-83-0 diphenylsilyl chloride 
• 583-55-1 1-Bromo-2-iodobenzene 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Synthesis of Dibenzosiloles through Electrocatalytic Sila-Friedel-Crafts Reaction

A novel electrocatalyzed method for the preparation of dibenzosiloles was developed through intramolecular C?H/Si?H dehydrogenative coupling strategy starting from biarylhydrosilanes. Both electro-donating and electro-withdrawing substitution groups were tolerated for this transformation, and the desired dibenzosilole products could be obtained in moderate to excellent yields. A sila-Friedel-Crafts reaction mechanism was proposed on the basis of previous literature and our controlled experiments. (Figure presented.).

Novel compound and organic light emitting device comprising the same

The present invention provides a novel compound and an organic light emitting device comprising the same. A compound represented by chemical formula 1 can be used as a material of an organic material layer of the organic light emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.COPYRIGHT KIPO 2020

Silyldefluorination of Fluoroarenes by Concerted Nucleophilic Aromatic Substitution

The reaction of readily generated silyl lithium reagents with various aryl fluorides to provide the corresponding aryl silanes is reported. DFT calculations reveal that the nucleophilic aromatic substitution of the fluoride anion by the silyl lithium reagent proceeds through concerted ipso substitution. In contrast to the classical nucleophilic aromatic substitution, this concerted ionic silyldefluorination also occurs on more electron-rich aryl fluorides.

Visible-Light Induced Radical Silylation for the Synthesis of Dibenzosiloles via Dehydrogenative Cyclization

A visible-light induced radical silylation to dibenzosiloles from biarylhydrosilanes is described. The products were obtained in satisfactory yields under mild and water/air compatible conditions, providing an efficient and practical method for the synthesis of difunctionalized siloles by using a cheap organic dye photocatalyst. The method is tolerated by a wide range of functional groups and has a broad substrate scope. Light/dark experiments and quantum yield measurements provided support for a photocatalytic pathway rather than a chain process. (Figure presented.).

9-Silafluorenes via base-promoted homolytic aromatic substitution (BHAS) - The electron as a catalyst

Transition-metal-free intramolecular radical silylation of 2-diphenylsilylbiaryls via base-promoted homolytic aromatic substitution (BHAS) to give 9-silafluorenes is reported. 2-Diphenylsilylbiaryls are readily prepared, and cross dehydrogenative silylation occurs with tert-butylhydroperoxide (TBHP) as a cheap stoichiometric oxidant in the presence of a small amount of tetrabutylammonium iodide (TBAI) as an initiator. These cyclizations are catalyzed by the electron.

A Catalytic SEAr Approach to Dibenzosiloles Functionalized at Both Benzene Cores

A general procedure for the catalytic preparation of dibenzosiloles functionalized at one or both benzene rings starting from readily available ortho-silylated biphenyls is reported. This method provides rapid access to silole building blocks substituted with chlorine atoms at both phenylene groups, thereby allowing catalytic access to directly polymerizable dibenzosiloles. Moreover, it is shown that, despite the involvement of highly electrophilic intermediates, a considerable range of Lewis-basic, for example, oxygen- and nitrogen-containing, functional groups is tolerated. The mechanism of this intramolecular electrophilic aromatic substitution (SEAr) proceeds through a sulfur-stabilized silicon cation, generated catalytically from the hydrosilane precursor.

B(C6F5)3-catalyzed synthesis of benzofused-siloles

The dehydrosilylation of 2-(SiR2H)-biphenyls catalyzed by B(C6F5)3 and a weak base forms silafluorenes with H2 as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B(C6F5)3 also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel-Crafts reaction facilitated by a weak base.

Versatile synthesis of blue luminescent siloles and germoles and hydrogen-bond-assisted color alteration

(Figure Presented) Deeper in the blue: A versatile procedure has been developed for the preparation of photoluminescent siloles and germoles by palladium-catalyzed cross-coupling of 2,2′-diiodobiaryls with dihydrosilanes and -germanes. The dibenzosiloles and -germoles with ester moieties on the aromatic ring exhibited different emission wavelengths in the solution and crystalline states, attributable to the intermolecular interactions (see figure).

Modular approach to silicon-bridged biaryls: Palladium-catalyzed intramolecular coupling of 2-(arylsilyl)aryl triflates

(Chemical Equation Presented) Bridge of Si: Intramolecular direct arylation of 2-(arylsilyl)aryl triflates is catalyzed smoothly by Pd(OAc) 2/PCy3 in the presence of Et2NH in dimethylacetamide (DMA), giving rise to the corresponding silicon-bridged biaryls in good to excellent yields. The new approach has led to the synthesis of a silicon-bridged 2-phenylindole (see scheme) that exhibits blue photoluminescence in the solid state with extremely high quantum yields.

Silacyclopentadiene derivatives and an organic electroluminescent element obtained by using the silacyclopentadiene derivative

An electroluminescence element (EL) obtained by using a silacyclopentadiene. derivation expressed by the general formula (I) and the derivative are provided. STR1 (wherein X and Y are independently hydrocarbon radicals with from 1 to 6 atoms and R1 to R4 are hydrogen, halogens, alkyl radicals with from 1 to 6 carbon atoms, or a condensed (un)substituted ring if being adjacent).