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Usage

Uses

Used in Organic Electronics:
5,6-DibroMo-2,1,3-benzothiadiazole is used as a key component in the development of organic electronics for its ability to enhance photovoltaic performance. Its unique electronic properties make it an appealing choice for researchers and scientists in this field.
Used in Light-Emitting Diodes (LEDs):
5,6-DibroMo-2,1,3-benzothiadiazole is used as a material in the production of light-emitting diodes (LEDs), where its electron-deficient properties contribute to improved device performance.
Used in Solar Cells:
In the solar cell industry, 5,6-DibroMo-2,1,3-benzothiadiazole is used as a material to improve the efficiency of solar energy conversion, leveraging its electron-deficient nature to enhance photovoltaic performance.
Used in Transistors:
5,6-DibroMo-2,1,3-benzothiadiazole is used as a component in the manufacturing of transistors, where its electronic properties are crucial for the device's operation and efficiency.
Used in the Synthesis of Organic Semiconducting Materials:
5,6-DibroMo-2,1,3-benzothiadiazole is used as a precursor in the synthesis of various organic semiconducting materials, which are essential for the advancement of organic electronics.

Upstream product

• 54558-18-8 1,2-dinitro-4,5-dibromobenzene 
• 49764-63-8 4,5-dibromo-1,2-diaminobenzene 
• 49633-28-5 1,2-bis-(p-methylphenylsulfonamido)-benzene 
• 95-54-5 1,2-diamino-benzene 
• 583-53-9 2,3-dibromobenzene 
• 88617-67-8 N-[4,5-dibromo-2-(p-tolylsulfonylamino)phenyl]-4-methylbenzenesulfonamide 

Downstream Products

• 49764-63-8 4,5-dibromo-1,2-diaminobenzene 
• 129365-93-1 4,5-diaminophthalonitrile 

Relevant academic research and scientific papers

Linear and star-shaped pyrazine-containing acene dicarboximides with high electron-affinity

A series of linear and star-shaped pyrazine-containing acene molecules 1a-b, 2a-b and 3 substituted by dicarboximide groups are synthesized via condensation reactions between o-diamine and dione. High electron affinity (up to 4.01 eV) is achieved due to t

Multinuclear Phthalocyanine-Fused Molecular Nanoarrays: Synthesis, Spectroscopy, and Semiconducting Property

The post-cyclization strategy rather than the conventional ante-cyclotetramerization method was employed for the synthesis of multinuclear phthalocyanine-fused molecular nanoarrays. Reaction of 2,3,9,10,16,17-hexakis(2,6-dimethylphenoxy)-23,24-diaminophth

Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2

Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.

A benzothiadiazole-supported N-heterocyclic carbene and its rhodium and iridium complexes

A new N-heterocyclic carbene containing a fused benzothiadiazole (BTD) moiety, 5,7-bis(1,1-dimethylethyl)-5H-imidazo[4,5-f]-2,1,3-benzothiadiazol-6-ylidene (1), was generated by deprotonation of the corresponding tetrafluoroborate salt. The salt precursor

Photodriven Multi-electron Storage in Disubstituted RuII Dppz Analogues

Four derivatives of the laminate acceptor ligand dipyrido-[3,2-a:2′,3′-c]phenazine (dppz) and their corresponding ruthenium complexes, [Ru(phen)2(dppzX2)]2+, were prepared and characterized by NMR spectroscopy, ESI-MS, and elemental analysis. The new ligands, generically denoted dppzX2, were symmetrically disubstituted on the distal benzene ring to give 10,13-dibromodppz (dppz-p-Br), 11,12-dibromodppz (dppz-o-Br), 10,13-dicyanodppz (dppz-p-CN), 11,12-dicyanodppz (dppz-o-CN). Solvated ground state MO calculations of the ruthenium complexes reveal that these electron-withdrawing substituents not only lower the LUMO of the dppz ligand (dppz(CN)22dppz), but that the para disubstitution results in a lower LUMO than the ortho disubstitution (dppz-p-CN(dppz-o-CN), and dppz-p-Brdppz-o-Br). The validity of the calculations was confirmed experimentally using cyclic voltammetry. Of the complexes evaluated in this study, only the dicyanodppz complexes showed multiple dppz-based reductions prior to reduction of the phen ligands. The capacity to form singly and doubly reduced dppz-based anions at modest reduction potentials was confirmed using a combination of spectroelectrochemical and chemical titration methods. When subjected to photolysis with visible light in the presence of a sacrificial donor, such as triethylamine, both cyano complexes showed multi-electron reduction. The other complexes only show a single reduction.

Bisthienylethenes containing a benzothiadiazole unit as a bridge: Photochromic performance dependence on substitution position

A conveniently synthesized photochromic compound, BTB-1, containing an unprecedented six-mem- bered 2, 1, 3-benzothiadiazole unit as the center ethene bridge, possesses good photochromic performance, with a high cyclization quantum yield and moderate fatigue resistance in solution or an organogel system. The fluorescence of BTB-1 can be modulated by solvato- and photochromism. However, the analogue BTB-2, in which the di- methylthiophene substituents are relocated to the 5, 6-positions of benzothia- diazole, does not show any detectable photochromism. To the best of our knowledge, this is the first example of six-membered bridge bisthienylethenes (BTEs) in which the photochromism can be controlled by the substitution position. The photochromism difference is elucidated by the analysis of resonance structure, the Woodward- Hoffmann rule, and theoretical calculations on the ground-state potential- energy surface. In a well-ordered single-crystal state, BTB-1 adopts a relatively rare parallel conformation, and forms an interesting two-dimensional structure due to the presence of multiple directional intermolecular interactions, including C-H-N and C-H-S hydrogen-bonding interactions, and π stacking interactions. This work contributes to several aspects for developing novel photochromic BTE systems with fluorescence modulation and performances controlled by substitution position in different states (solution, or- ganogel, and single crystal).

A reliable route to 1,2-diamino-4,5-phthalodinitrile

Starting from o-phenylenediamine, we have developed a new and reliable route to 1,2-diamino-4,5-phthalodinitrile that is based on the reductive desulfurisation of 5,6-dicyano-2,1,3-benzothiadiazole with sodium borohydride. The reaction sequence uses only

Preparations and Template Cyclotetramerisations of 2,1,3-Benzothia(selena)diazole-5,6-dicarbonitriles

2,1,3-Benzothiadiazole-5,6-dicarbonitrile 1b, and the corresponding selena derivative 2b, have been prepared in multistep syntheses.Template cyclotetramerisations with copper or magnesium powder in an inert atmosphere give the thiadazole substituted phtha