244-95-1

Usage

Uses

Used in Organic Electronics Industry:
Dibenzoselenophene is used as a building block for the development of organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs) due to its unique chemical and electronic properties.
Used in Material Science:
Dibenzoselenophene is used as a component in the research and development of new materials for electronic and optoelectronic devices, leveraging its structure and properties to enhance device performance.
Used in Medicinal Chemistry:
Dibenzoselenophene is used as a building block in the design of new pharmaceutical compounds, with potential applications in medicinal chemistry for the development of novel therapeutic agents.

InChI:InChI=1/C12H8Se/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H

Upstream product

• 1016-05-3 dibenzothiophene sulfone 
• 115081-09-9 1,2-di([1,1'-biphenyl]-2-yl)diselane 
• 262-30-6 selenanthrene 
• 30467-70-0 dibenzoselenophene Se-oxide 
• 591-51-5 phenyllithium 
• 110155-06-1 5-phenyl-dibenzoselenophenium; chloride 
• 147452-19-5 2-methylseleno-2',5'-dimethylbiphenyl 
• 67-56-1 methanol 
• 19615-37-3 bis(2,2'-bisphenylylene)selenurane 
• 64-17-5 ethanol 
• 1455-13-6 deuteromethanol 
• 645-96-5 Benzeneselenol 
• 75-66-1 2-methylpropan-2-thiol 
• 108-98-5 thiophenol 

Downstream Products

• 565454-22-0 4-dibenzoselenophen-2-yl-4-oxo-butyric acid 
• 132-65-0 dibenzothiophene 
• 7428-92-4 dibenzoselenophen-2-ylamine 
• 858426-29-6 4-dibenzoselenophen-2-yl-butyric acid 
• 565454-26-4 dibenzoselenophen-2-yl-carbamic acid ethyl ester 
• 115164-87-9 biphenSe*I₂ 

Related news

Halogenation of Dibenzoselenophene (cas 244-95-1) and Dibenzo[1,2]diselenine09/28/2019

The syntheses of the selenium containing heterocycles dibenzoselenophene (1 ≡ biphenSe) and dibenzo[1,2]diselenine (2 ≡ biphenSe2) were optimized. The halogenation reactions of 1 and 2 with XeF2, SO2Cl2, Br2 and I2 were performed and the corresponding products characterized. In the case of 1, ...detailed

Relevant academic research and scientific papers

Metal-Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium

This work reports a green method for the synthesis of aryl selenocyanates via a three-component reaction of arylboronic acids, Se powder, and trimethylsilyl cyanide (TMSCN) under metal-free and additive-free conditions. Remarkably, TMSCN acts as not only the substrate, but also the catalyst. Various selenaheterocycles can be also accessed with a catalytic amount of TMSCN.

Synthesis of Selenaheterocycles via Visible-Light-Mediated Radical Cyclization

An approach for the synthesis of selenaheterocycles starting from aryl diazonium salts was developed. The one-pot process and subsequent visible-light-mediated silver-catalyzed cyclization enabled the synthesis of selenaheterocycles in the absence of a photocatalyst. The reactions were carried out under mild conditions without the use of toxic or sensitive reagents. (Figure presented.).

Visible light-induced photodeoxygenation of polycyclic selenophene Se-oxides

Photodeoxygenation of dibenzothiophene S-oxide (DBTO) is believed to produce ground-state atomic oxygen [O(3P)] in solution. Compared with other reactive oxygen species (ROS), O(3P) is a unique oxidant as it is potent and selective. Derivatives of DBTO have been used as O(3P)-precursors to oxidize variety of molecules, including plasmid DNA, proteins, lipids, thiols, and other small organic molecules. Unfortunately, the photodeoxygenation of DBTO requires ultraviolet irradiation, which is not an ideal wavelength range for biological systems, and has a low quantum yield of approximately 0.003. In this work, benzo[b]naphtho[1,2-d]selenophene Se-oxide, benzo[b]naphtho[2,1-d]selenophene Se-oxide, dinaphtho[2,3-b:2’,3’-d]selenophene Se-oxide, and perylo[1,12-b,c,d]selenophene Se-oxide were synthesized, and their ability to utilize visible light for generating O(3P) was interrogated. Benzo[b]naphtho[1,2-d]selenophene Se-oxide produces O(3P) upon irradiation centered at 420 nm. Additionally, benzo[b]naphtho[1,2-d]selenophene Se-oxide, benzo[b]naphtho[2,1-d]selenophene Se-oxide, and dinaphtho[2,3-b:2’,3’-d]selenophene Se-oxide produce O(3P) when irradiated with UVA light and have quantum yields of photodeoxygenation ranging from 0.009 to 0.33. This work increases the utility of photodeoxygenation by extending the range of wavelengths that can be used to generate O(3P) in solution.

Ag-Catalyzed Cyclization of Arylboronic Acids with Elemental Selenium for the Synthesis of Selenaheterocycles

A general method for the synthesis of five-membered and six-membered selenaheterocycles through Ag-catalyzed C?Se bond-forming reaction is reported. This reaction proceeds via intramolecular cyclization of arylboronic acids with selenium powder. Preliminary mechanism studies demonstrate that this transformation involves a selenium-centred radical intermediate. (Figure presented.).

VISIBLE LIGHT INDUCED PHOTOGENERATION OF GROUND STATE ATOMIC OXYGEN

The present invention generally relates to various polycyclic aromatic selenoxide compounds, methods for preparing these compounds, and methods of us these and other compounds to generate ground state atomic oxygen.

Synthetic method of dibenzoselenophene compound

The invention discloses a synthetic method for preparing a dibenzoselenophene compound. According to the method, a C-Se bond is formed through free radical cyclization of a biaryl boric acid substratecatalyzed by TMSCN and selenium powder, so that the dibenzoselenophene compound is constructed. The new strategy has the advantages of no metal participation, no additive promotion, wide substrate range, good functional group compatibility, simple operation, high yield and the like.

Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis

An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.

Mo-Based Oxidizers as Powerful Tools for the Synthesis of Thia- and Selenaheterocycles

A highly efficient synthetic protocol for the synthesis of thia- and selenaheterocycles has been developed. By employing a MoCl5-mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide or diselenide precursors, a high atom efficiency was achieved.

Palladium(II)-Catalyzed Synthesis of Dibenzothiophenes from 2-Biphenylyl Disulfides by C?H Functionalization

The palladium-catalyzed oxidative preparation of dibenzothiophene derivatives from 2-biphenylyl disulfides by C?H functionalization is described herein. This procedure shows a high tolerance toward various functional groups and does not require the further addition of a metal oxidant, a base, or a ligand. Also, the present method was applied to the facile preparation of dibenzoselenophene.

Green Preparation of Dibenzothiophene Derivatives Using 2-Biphenylyl Disulfides in the Presence of Molecular Iodine and Its Application to Dibenzoselenophene Synthesis

A protocol for the direct preparation of dibenzothiophenes from 2-biarylyl disulfides in the presence of an economic and ecological oxidant, molecular iodine, was explored. This protocol was used for the direct preparation of dibenzoselenophene.