141215-32-9

Basic information

• Product Name: 4,7-dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine
• Synonyms: 4,7-dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine;4,7-Dibromo-benzo[1,2,5]thiadiazole-5,6-diamine;4,7-dibromo-2,1,3-benzothiadiazole-5,6-diamine
• CAS NO: 141215-32-9
• Molecular Formula: C₆H₄Br₂N₄S
• Molecular Weight: 323.99576
• Mol File: 141215-32-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 423.0±40.0 °C(Predicted)
• Appearance: /
• Density: 2.375±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -1.00±0.50(Predicted)
• CAS DataBase Reference: 4,7-dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine(141215-32-9)
• EPA Substance Registry System: 4,7-dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine(141215-32-9)

Safety Data

• Hazardous Substances Data: 141215-32-9(Hazardous Substances Data)

Usage

General Description

4,7-dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine is a chemical compound that belongs to the class of benzo[c][1,2,5]thiadiazole derivatives. It is a diamine compound, meaning it contains two amino groups. The presence of bromine atoms at the 4th and 7th positions of the benzo[c][1,2,5]thiadiazole ring makes this compound a brominated derivative. This chemical has potential applications in the field of organic synthesis and materials science, particularly in the development of organic semiconductors and optoelectronic devices. Further research and exploration of its properties and potential uses are warranted for a deeper understanding of its potential applications.

Upstream product

• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 76186-72-6 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole 

Downstream Products

• 1262727-09-2 4,9-dibromo-6,7-diphenyl [1,2,5]thiadiazolo-[3,4-g]quinoxaline 
• 1233872-22-4 4,9-dibromo-6,7-bis(4-(octyloxy)phenyl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline 
• 1268697-46-6 4,9-dibromo-6,7-bis(4-dodecylphenyl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline 
• 165617-59-4 4,8-dibromo-1H,5H-benzo[1,2-c:4,5-c']bis([1,2,5] thiadiazole) 

Relevant articles and documents

Potentiometric, electronic structural, and ground- and excited-state optical properties of conjugated bis[(porphinato)zinc(II)] compounds featuring proquinoidal spacer units

We report the synthesis, optical, electrochemical, electronic structural, and transient optical properties of conjugated (porphinato)zinc(II)-spacer- (porphinato)zinc(II) (PZn-Sp-PZn) complexes that possess intervening conjugated Sp structures having varying degrees of proquinoidal character. These supermolecular PZn-Sp-PZn compounds feature Sp moieties {(4,7-diethynylbenzo[c] [1,2,5]thiadiazole (E-BTD-E), 6,13-diethynylpentacene (E-PC-E), 4,9-diethynyl-6,7-dimethyl[1,2,5]thiadiazolo[3,4-g]quinoxaline (E-TDQ-E), and 4,8-diethynylbenzo[1,2-c:4,5-c′]bis([1,2,5]thiadiazole) (E-BBTD-E)} that regulate frontier orbital energy levels and progressively increase the extent of the quinoidal resonance contribution to the ground and electronically excited states, augmenting the magnitude of electronic communication between terminal (5,-10,20-di(aryl)porphinato)zinc(II) units, relative to that evinced for a bis[(5,5′,-10,20-di(aryl)porphinato)zinc(II)]butadiyne benchmark (PZnE-EPZn). Electronic absorption spectra show significant red-shifts of the respective PZn-Sp-PZn x-polarized Q state (S0 → S1) transition manifold maxima (240-4810 cm-1) relative to that observed for PZnE-EPZn. Likewise, the potentiometrically determined PZn-Sp-PZn HOMO-LUMO gaps (E1/20/+ - E1/2-/0) display correspondingly diminished energy separations that range from 1.88 to 1.11 eV relative to that determined for PZnE-EPZn (2.01 eV). Electronic structure calculations provide insight into the origin of the observed PZn-Sp-PZn electronic and optical properties. Pump-probe transient spectral data for these PZn-Sp-PZn supermolecules demonstrate that the S1 → S n transition manifolds of these species span an unusually broad spectral domain of the NIR. Notably, the absorption maxima of these S 1 → Sn manifolds can be tuned over a 1000-1600 nm spectral region, giving rise to intense excited-state transitions ～4000 cm-1 lower in energy than that observed for the analogous excited-state absorption maximum of the PZnE-EPZn benchmark; these data highlight the unusually large quinoidal resonance contribution to the low-lying electronically excited singlet states of these PZn-Sp-PZn species. The fact that the length scales of the PZn-Sp-PZn species (～25 A) are small with respect to those of classic conducting polymers, yet possess NIR S1 → Sn manifold absorptions lower in energy, underscore the unusual electrooptic properties of these conjugated structures.

Synthetic Antenna Functioning As Light Harvester in the Whole Visible Region for Enhanced Hybrid Photosynthetic Reaction Centers

The photosynthetic reaction center (RC) from the Rhodobacter sphaeroides bacterium has been covalently bioconjugated with a NIR-emitting fluorophore (AE800) whose synthesis was specifically tailored to act as artificial antenna harvesting light in the entire visible region. AE800 has a broad absorption spectrum with peaks centered in the absorption gaps of the RC and its emission overlaps the most intense RC absorption bands, ensuring a consistent increase of the protein optical cross section. The covalent hybrid AE800-RC is stable and fully functional. The energy collected by the artificial antenna is transferred to the protein via FRET mechanism, and the hybrid system outperforms by a noteworthy 30% the overall photochemical activity of the native protein under the entire range of visible light. This improvement in the optical characteristic of the photoenzyme demonstrates the effectiveness of the bioconjugation approach as a suitable route to new biohybrid materials for energy conversion, photocatalysis, and biosensing.

Ester-substituted heterocyclic aromatic conjugated skeleton and polymer material and application thereof

The invention belongs to the technical field of conjugated polymers, and particularly relates to an ester-substituted aromatic heterocyclic conjugated skeleton and a polymer material and application thereof. The ester-substituted heterocyclic aromatic conjugated skeleton and the polymer material thereof have a larger conjugated plane structure and are more beneficial to intramolecular charge transfer, and compared with the traditional heterocyclic aromatic polymer material, the ester-substituted heterocyclic aromatic conjugated skeleton has the advantages that on the basis of the original chemical structure of the polymer, two strong electron-withdrawing functional groups, namely ester groups, are introduced, so that the aromatic heterocyclic conjugated skeleton has stronger electron-withdrawing capability, the polymer has lower LUMO energy level, redder absorption spectrum and excellent long-wave range light absorption performance, and the ester-substituted aromatic heterocyclic conjugated skeleton and the polymer material thereof are used as photothermal conversion materials to be applied to the field of photoacoustic imaging, and have the advantages of higher photothermal conversion efficiency, better light stability, better imaging effect and the like.

Infrared organic light-emitting material based on benzobisthiadiazole derivative

The invention discloses an infrared organic light-emitting material based on benzobisthiadiazole derivative; in the invention, a characteristic compound, in which the type of connecting groups with benzobisthiadiazole and symmetric or asymmetric bonding modes are defined, serves as the infrared organic light-emitting material, so that charge balance in a luminescent layer in an organic electroluminescent material is achieved, and the organic electronic component is improved in luminous efficiency, thermal stability, color purity and luminescent life, and the driving voltage of the device is reduced. The infrared organic light-emitting material based on benzobisthiadiazole derivative is a potential TADF (thermal-activated delayed fluorescence) material, is high in performance and high in external quantum efficiency, and has a potential application prospect.

Thiadiazoloquinoxaline and benzodithiophene bearing polymers for electrochromic and organic photovoltaic applications

Two novel thiadiazoloquinoxaline and benzodithiophene (BDT) bearing copolymers were designed and synthesized. Different BDT units (alkoxy and thiophene substituted) were used as donor materials and the effect of alkoxy and thiophene substitution on the electrochemical, spectroelectrochemical and photovoltaic properties were investigated. Both polymers exhibited low oxidation potentials at around 0.90 V and low optical band gaps at around 1.00 eV due to the insertion of electron poor thiadiazoloquinoxaline unit into the polymer backbone. Both P1 (poly-6,7-bis(3,4-bis(decyloxy)phenyl)-4-(4,8-bis(nonan-3-yloxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-[1, 2, 5]thiadiazolo[3,4-g]quinoxaline) and P2 (poly- 4-(4,8-bis(5-(nonan-3-yl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophen-2-yl)-6,7-bis(3,4-bis(decyloxy)phenyl)-[1, 2, 5]thiadiazolo[3,4-g]quinoxaline) exhibited multichromic behavior with different tones of greenish yellow and gray in the neutral and fully oxidized states, respectively. In addition, both polymers revealed very high optical contrasts (～87%) in the NIR region which make these promising polymers good candidates for NIR applications. Finally, in order to explore the organic photovoltaic performances, P1 and P2 were mixed with PC71BM in the active layer of organic solar cells (OSCs) by conventional device structure. As a result P1 and P2 based devices revealed power conversion efficiencies (PCEs) of 0.33% and 0.60% respectively. However, the additive treatment enhanced PCE from 0.49 to 0.73% for P2 based devices.