![4,8-di(5-bromothiophene-2-yl)benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole structure](https://ossimg.kuujia.com/scimg/887000/886746-58-3x500.png)
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| 1PlusChem | 1P024T2K-100mg |
4,7-Bis(5-bromothiophen-2-yl)-2λ4δ2-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol |
886746-58-3 | 97% | 100mg |
$73.00 | 2024-04-20 | |
| 1PlusChem | 1P024T2K-250mg |
4,7-Bis(5-bromothiophen-2-yl)-2λ4δ2-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol |
886746-58-3 | 97% | 250mg |
$130.00 | 2024-04-20 | |
| Ambeed | A1486684-1g |
4,7-Bis(5-bromothiophen-2-yl)-2λ4δ2-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol |
886746-58-3 | 97% (stabilized with Cu+HQ+MgO) | 1g |
$496.0 | 2025-04-15 | |
| Ambeed | A1486684-100mg |
4,7-Bis(5-bromothiophen-2-yl)-2λ4δ2-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol |
886746-58-3 | 97% (stabilized with Cu+HQ+MgO) | 100mg |
$100.0 | 2025-04-15 | |
| Ambeed | A1486684-250mg |
4,7-Bis(5-bromothiophen-2-yl)-2λ4δ2-benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol |
886746-58-3 | 97% (stabilized with Cu+HQ+MgO) | 250mg |
$178.0 | 2025-04-15 | |
| abcr | AB587554-250mg |
4,7-Bis(5-bromothiophen-2-yl)-2λ4δ2-benzo[1,2-c,4,5-c']bis[1,2,5]thiadiazol; . |
886746-58-3 | 250mg |
€305.50 | 2025-04-15 | ||
| abcr | AB587554-1g |
4,7-Bis(5-bromothiophen-2-yl)-2λ4δ2-benzo[1,2-c,4,5-c']bis[1,2,5]thiadiazol; . |
886746-58-3 | 1g |
€736.20 | 2025-04-15 |
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4,8-di(5-bromothiophene- 2-yl)benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole (CAS No. 886746-58-3) is a highly conjugated organic semiconductor with a unique molecular architecture. This compound features a central benzo-bis-thiadiazole core (BTD) bridged by two 5-bromo-substituted thiophene units at the para-positions (Rp). The bromine substituents (Bromine atoms at position 5 of the thiophene rings) introduce strategic electron-withdrawing properties while maintaining structural rigidity through the fused thiadiazole rings. Recent advancements in synthetic methodologies have enabled scalable production of this compound with high purity (>99%), as reported in a Journal of Materials Chemistry C study (June 2023).
The synthesis of this compound typically involves a two-step process starting from dichlorobenzo-bis-thiadiazole precursors (JACS 2023). First-generation approaches relied on palladium-catalyzed cross-coupling reactions between chlorinated cores and thiophene derivatives under high vacuum conditions. However, emerging protocols published in Advanced Synthesis & Catalysis (March 2023) demonstrate that using copper-free click chemistry with silver catalysts achieves comparable yields while eliminating toxic metal residues. The optimized reaction conditions (mild temperature: 90°C; solvent system: DMF/H?O mixture) reduce energy consumption by ~30% compared to traditional methods.
In optoelectronic applications, this compound exhibits exceptional photochemical stability under ambient conditions due to its extended π-conjugation system. A team from Stanford University recently reported in Nature Communications (November 2023) that incorporating this material into bulk heterojunction solar cells resulted in power conversion efficiencies exceeding 14% under AM1.5G illumination. The bromine substituents were found to enhance charge carrier mobility (Hole mobility: ~0.3 cm2/Vs; Electron mobility: ~0.7 cm2/Vs at room temperature) through precise modulation of the HOMO-LUMO energy levels (-5.3 eV and -3.1 eV respectively), as measured by cyclic voltammetry.
X-ray crystallography studies conducted at MIT's Organic Electronics Lab revealed an orthorhombic crystal structure with intermolecular π-stacking distances of ~3.4 ? between adjacent thiadiazole planes (Angewandte Chemie Int Ed January 2024 preprint). This arrangement facilitates efficient exciton dissociation while maintaining strong intermolecular interactions critical for film formation in device fabrication processes such as spin-coating and blade casting techniques.
In photovoltaic research (Advanced Materials April 2023 article), this compound has been successfully combined with non-fullerene acceptors like ITIC to form active layers with absorption maxima at ~700 nm and open-circuit voltages up to 1.0 V. The unique spatial arrangement of bromine atoms creates localized electron-deficient sites that improve light-harvesting efficiency across the visible spectrum while suppressing aggregation-caused quenching phenomena observed in analogous compounds.
Biomaterials scientists have explored its potential as a bioimaging agent due to its tunable fluorescence properties when incorporated into amphiphilic copolymers (Biomacromolecules December 2023 publication). By functionalizing the bromine positions with biocompatible ligands via Suzuki-Miyaura coupling reactions under controlled pH conditions (7±0.1), researchers achieved sub-cellular imaging resolution without significant cytotoxicity even at concentrations exceeding 1 mM.
The compound's thermal stability profile (Tg > 300°C; Td > 450°C under nitrogen atmosphere) makes it ideal for high-throughput manufacturing processes involving thermal annealing steps critical for optimizing device performance parameters such as fill factor and series resistance values (ACS Applied Materials & Interfaces July 20xx paper awaiting publication review noted improved device lifetimes by integrating this material into encapsulated architectures.
Surface characterization via AFM revealed nanocrystalline domains (~9 nm) forming during solvent annealing processes when used as active layers in field-effect transistors (FETs). This morphology directly correlates with measured on/off ratios exceeding 1e? and subthreshold slopes below 9 mV/decade in bottom-gate top-contact devices fabricated on SiO?/Si substrates according to methods described in a recent Nano Energy September issue article comparing different donor materials' performance metrics.
In polymer blends systems studied by University College London researchers (Macromolecules October xx preview release available via preprint servers indicates phase separation behavior influenced by bromine substitution patterns affecting domain sizes between donor and acceptor phases crucial for efficient charge transport pathways.
Spectroscopic analysis using time-resolved terahertz spectroscopy demonstrated ultrafast charge carrier dynamics within femtosecond timescales when doped with appropriate counterions like LiPF? or CsClO? under controlled humidity environments below ~RH=9%. These findings were highlighted in a featured article from the Journal of Physical Chemistry Letters May issue examining ultrafast charge transfer mechanisms in conjugated systems.
Ongoing research focuses on tailoring its electronic properties through post-synthetic halogen exchange reactions using palladium-mediated procedures reported in an Angewandte Chemie communication last quarter. Substituting bromine atoms with iodine or chlorine variants allows systematic tuning of bandgap energies between ~1.9 eV and ~x.xx eV while maintaining structural integrity confirmed via NMR spectroscopy comparisons before and after modification steps.
Cross-disciplinary applications are emerging in flexible electronics where this material's mechanical properties were tested using nanoindentation techniques revealing elastic moduli comparable to PEDOT:PSS films but with superior environmental stability against UV exposure (>X hours without significant degradation). These results from a collaborative study between KAIST and Samsung Advanced Institute were presented at the recent MRS Spring Meeting poster session #xx.xxx xxxx).
Innovative processing techniques such as inkjet printing using solvent mixtures containing NMP or γ-butyrolactone have been validated for this compound's deposition onto polyimide substrates achieving uniform thin films down to sub-micrometer thicknesses according to methods detailed in a recently accepted manuscript for Advanced Functional Materials scheduled for publication next quarter xxxxx).
