31574-87-5

Usage

Uses

Used in Organic Synthesis:
2,8-Dibromodibenzothiophene is utilized as a starting material or intermediate for the synthesis of novel 2,8-disubstituted dibenzothiophenes. This is achieved through palladium-catalyzed C-N or C-C bond formation reactions, which are crucial for the development of various organic compounds with potential applications in different fields.
Used in Organic Electroluminescent Derivatives:
Furthermore, 2,8-Dibromodibenzothiophene serves as a starting material for creating organic electroluminescent derivatives. These derivatives are important in the field of optoelectronics, particularly for the development of organic light-emitting diodes (OLEDs) and other light-emitting technologies, due to their unique photophysical and electrochemical properties.

InChI:InChI=1/C12H6Br2S/c13-7-1-3-11-9(5-7)10-6-8(14)2-4-12(10)15-11/h1-6H

Upstream product

• 132-65-0 dibenzothiophene 
• 1013-23-6 Dibenzothiophene sulfoxide 
• 56-23-5 tetrachloromethane 
• 7446-70-0 aluminium trichloride 
• 7726-95-6 bromine 
• 92-85-3 Thianthrene 

Downstream Products

• 1207-15-4 2,8-dimethyldibenzothiophene 
• 40307-15-1 2,8-dibromo-5H-5λ⁶-dibenzo[b,d]thiophene-5,5-dione 
• 113525-39-6 2,8-bis-(S-benzyl)dibenzothiophene 
• 105404-98-6 2,8-bis-(S-methyl)dibenzothiophene 
• 113538-39-9 2,8-bis-(S-p-tolyl)dibenzothiophene 
• 404906-09-8 2,8-bis(phenylethynyl)dibenzothiophene 
• 74291-12-6 C₂₈H₁₆O₄S 
• 913738-04-2 (2,8-dibenzothiophenediyl)bis-9H,9'H-carbazole 
• 1345827-41-9 9-(8-(diphenylphosphoryl)dibenzo[b,d]thiophene-2-yl)-9H-carbazole 
• 1258319-81-1 C₃₆H₂₆P₂S 
• 1019842-99-9 2,8-bis(diphenylphosphoryl)dibenzo[b,d] thiophene 
• 1422184-05-1 C₃₀H₂₀BrNS 
• 105404-91-9 2,8-diiododibenzo[b,d]thiophene 

Relevant academic research and scientific papers

Synthesis and optical and electrochemical properties of a bispyrimidinium-dibenzothiophene-S,S-dioxide-based cationic conjugated polymer

A novel n-type cationic conjugated polymer (PFSOmiCl), consisting of bispyrimidinium-dibenzothiophene-S,S-dioxide and fluorene scaffolds, was developed from its polymeric precursor (PFSOmi) through an intramolecular cyclization reaction. In comparison with PFSOmi, PFSOmiCl exhibits significant bathochromical absorption and photoluminescence spectra in both solution and film form, as well as a more hydrophilic film surface. Cyclic voltammetry tests demonstrate that PFSOmiCl possesses a deep lowest unoccupied molecular orbital (LUMO) energy level of??4.18?eV, which is comparable to the LUMO energy levels of common fullerene derivatives. These unique properties endow PFSOmiCl with great utilization potential in organic optoelectronic devices. Moreover, this research offers a novel guideline for designing new conjugated polyelectrolytes.

Fluorescent and electrochromic polymers from 2,8-di(carbazol-9-yl)dibenzothiophene and its S,S-dioxide derivative

We report the synthesis and characterization of two carbazole-endcapped monomers, namely 2,8-di(carbazol-9-yl)dibenzothiophene (SCz) and 2,8-di(carbazol-9-yl)dibenzothiophene S,S-dioxide (SO2Cz), and their derived polymers PSCz and PSO2Cz prepared by both FeCl3 oxidative coupling and electropolymerization processes. The dilute solutions of PSCz and PSO2Cz prepared by chemical oxidative coupling exhibited fluorescent and solvatochromic behavior. Thin polymeric films could be robustly electrodeposited onto the surface of the ITO-glass substrate by repetitive cyclic voltammetry scanning of monomers SCz and SO2Cz in an electrolyte solution between 0 and 1.8?V. The electrochemically generated polymer films exhibited two reversible oxidation redox couples due to successive oxidations of the biscarbazole unit. These polymer films also revealed good electrochemical and electrochromic stability, with coloration change from a colorless neutral state to yellow, green and blue oxidized states. Switching ability of the polymers was evaluated by kinetic studies upon measuring the percent transmittance (%T) at their maximum contrast point, indicating that the polymers exhibit moderate electrochromic performance.

High-performance bipolar host materials for blue TADF devices with excellent external quantum efficiencies

New bipolar host molecules composed of carbazole, pyridoindole, and dibenzothiophene (DBT) were synthesized for blue thermally activated delayed fluorescence (TADF)-based organic light-emitting diodes (OLEDs). 2,8-Di(9H-carbazol-9-yl)dibenzo[b,d]thiophene, 9-(8-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-2-yl)-9H-pyrido[2,3-b]indole, and 2,8-bis(9H-pyrido[2,3-b]indol-9-yl)dibenzo[b,d]thiophene were prepared based on the selective reactivity at the 2,8-positions of DBT. The new symmetric and asymmetric host materials exhibited high triplet energies (2.89-2.95 eV). 4,5-Di(9H-carbazol-9-yl)phthalonitrile (2CzPN) was selected as an emitting dopant for achieving sky-blue emissions in TADF-OLEDs. 2CzPN-doped TADF-OLEDs, whose configuration is ITO (50 nm)/HATCN (7 nm)/TAPC (75 nm)/host:6% 2CzPN (20 nm)/TmPyPB (50 nm)/LiF (15 nm)/Al (100 nm), showed low driving voltages and high external quantum efficiencies (EQEs). These results are attributed to the well-controlled bipolar character of the host giving a better charge balance in the emitting layer. In particular, the device containing ZDN:6% 2CzPN showed an unprecedentedly high EQE of 25.7% (at 0.074 mA cm-2).

Novel thienyl-dibenzothiophene oligomers end-capped by hexylphenyl groups as potential organic semiconductor materials

Novel thienyl-dibenzothiophene oligomers end-capped by hexylphenyl groups, 2,8-bis[5-(4-n-hexylphenyl)-2-thienyl]dibenzothiophene (28HPTDBT) and 3,7-bis[5-(4-n-hexylphenyl)-2-thienyl]dibenzothiophene (37HPTDBT), have been synthesized using Stille cross-coupling reactions. Newly synthesized oligomers were investigated by Ultraviolet-visible (UV-vis) and photoluminescence (PL) spectroscopy, cyclic voltammogram, and thermal analysis. Strong intermolecular-interactions, appropriate energy band gaps and low HOMO energy levels imply that the two oligomers are promising candidate materials for durable organic electronic devices.

Novel dibenzothiophene chromophores with peripheral barbituric acceptors

A series of novel chromophores based on central 2,8-disubstituted dibenzothiophene (DBT) or dibenzothiophene-S,S-dioxide (DBTO) has been designed and prepared. The interconnection of DBT(O) central scaffold with two peripheral barbituric acceptors via various π-spacer allowed significant property tuning of target chromophores. Four new final chromophores and six DBT(O)-intermediates have been successfully synthesized and fully characterized. Experimental and calculated data showed that the fundamental properties are affected by the chromophore A-π-D-π-A or A-π-A-π-A arrangement (DBT vs. DBTO) and the π-linker (ethenylene vs. ethynylene). Thorough structure-property relationships have been elucidated and discussed in detail.

Novel phenylene-thiophene oligomer derivatives with dibenzothiophene 5,5-dioxide core: Synthesis, characterization, and applications in organic solar cells

Donor-acceptor-donor oligomers with dibenzothiophene 5,5-dioxide core and end-cap phenylene-thiophene substitutes were newly synthesized. New oligomers were characterized by UV-vis absorption and photoluminescence spectroscopy, cyclic voltammetry, and app

A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

We designed a straightforward synthetic route towards a full-fledged family of π-extended helicenes: superhelicenes. They have two hexa-peri-hexabenzocoronenes (HBCs) in common that are connected via a central five-membered ring. By means of structurally altering this 5-membered ring, we realized a versatile library of molecular building blocks. Not only the superhelicene structure, but also their features are tuned with ease. In-depth physico-chemical characterizations served as a proof of concept thereof. The superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was rounded-off by crystal structure analyses. Mixed stacks of M- and P-isomers led to twisted molecular wires. Using such stacks, charge-carrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

Small molecule light-emitting material based on naphthothiodibenzofuran unit, preparation method and applications thereof

The invention discloses a small molecule light-emitting material based on a naphthothiodibenzofuran unit, a preparation method and applications thereof, wherein the naphthothiodibenzofuran unit is beneficial to improving the electron affinity and promoting the injection and transmission of electrons, and has high fluorescence efficiency and high chemical stability. According to the invention, thesmall molecule light-emitting material based on the naphthothiodibenzofuran unit is obtained through a Suzuki or C-N coupling reaction, and has high thermal stability, good film-forming property and good dissolvability; and after the small molecule light-emitting material based on the naphthothiodibenzofuran unit is dissolved by adopting a common organic solvent, and the light emitting layer of alight-emitting diode is prepared through spin coating, vacuum evaporation, ink-jet printing or printing film formation.

Photophysical properties and optical power limiting ability of Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at different positions

Two series of Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at different positions have been synthesized. In the absorption spectra, the Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 3,6-position have blue-shift with respect to the corresponding analogs bearing fluorene-type ligands with ethynyl units at 2,7-position, showing better transparency in the visible light region. Moreover, the Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 3,6-position show stronger triplet emission than corresponding analogs bearing fluorene-type ligands with ethynyl units at 2,7-position in the photoluminescent (PL) spectra. Furthermore, these Pt(II) polyynes were applied to optical power limiting (OPL) field. The Pt(II) polyynes bearing fluorene-type ligands with ethynyl units at 2,7-position show better OPL performance than the corresponding analogs with fluorene-type ligands of ethynyl units at 3,6-position. Therefore, changing the position of the ethynyl units in fluorene-type ligands can not only effectively control the photophysical properties of the Pt(II) polyynes, but also has an important effect on their OPL ability.