288071-87-4

Basic information

• Product Name: 4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole
• Synonyms: 4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole;4,7-Bis(5-broMo-2-thienyl)-2,1,3-benzothiadiazole;4,7-di-2′-(5′-broMo)-thienyl-2,1,3-benzothiadiazole;2,1,3-Benzothiadiazole, 4,7-bis(5-broMo-2-thienyl)- 4,7-Bis(2-broMo-5-thienyl)-2,1,3-benzothiadiazole;2,1,3-Benzothiadiazole,4,7-bis(5-broMo-2-thienyl)-;4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole >=99.0% (HPLC)
• CAS NO: 288071-87-4
• Molecular Formula: C₁₄H₆Br₂N₂S₃
• Molecular Weight: 458.21
• Product Categories: BT monomers
• Mol File: 288071-87-4.mol

Chemical Properties

• Melting Point: 245.0 to 249.0 °C
• Boiling Point: 527.304 °C at 760 mmHg
• Flash Point: 272.704 °C
• Appearance: /
• Density: 1.898
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -1.63±0.50(Predicted)
• CAS DataBase Reference: 4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole(288071-87-4)
• EPA Substance Registry System: 4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole(288071-87-4)

Safety Data

• Hazard Codes: T
• Statements: 25-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 288071-87-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole is used as an organic synthesis intermediate for the development of new organic compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole is used as a pharmaceutical intermediate, aiding in the synthesis of new drugs and pharmaceutical products.
Used in Laboratory Research and Development:
4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole is utilized in laboratory research and development processes, where it serves as a key component in the creation of new materials and compounds for various applications.
Used in Chemical Production:
4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole is also used in chemical production processes, where it contributes to the synthesis of various chemical products and materials.
Used in Photovoltaic Solar Cell Devices:
In the field of photovoltaics, 4,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole is used as a key monomer in the synthesis of polymer semiconductors, such as PCDTBT, which are crucial for the development and efficiency of solar cell devices.

Synthesis

M4 (0.07 g, 0.233 mmol) was dissolved in 3.3 mLdry CHCl3 followed by addition of NBS (0.87 g, 0.489 mmol) at 0 °C.The reaction was conducted in dark by covering the flask withaluminium foil. The product was extracted with CHCl3 and thesolvent was evaporated to obtain crude product which was purifiedby silica gel column chromatography using 5% ethyl acetate/hexaneas eluent to obtain M5 as bright orange solid (0.101 g, 95%). Meltingpoint = 258 °C.

InChI:InChI=1S/C14H6Br2N2S3/c15-11-5-3-9(19-11)7-1-2-8(10-4-6-12(16)20-10)14-13(7)17-21-18-14/h1-6H

Upstream product

• 1003-09-4 2-bromothiophene 
• 1502834-32-3 4-(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole 
• 95-54-5 1,2-diamino-benzene 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 165190-76-1 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole 

Downstream Products

• 1380314-79-3 C₅₄H₄₂N₄O₄S₃ 
• 1402049-91-5 4,7-bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzothiadiazole 
• 840531-02-4 4,7-bis(5-(3-hydroxyphenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole 
• 1445719-57-2 4-(5-(4-(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)-thiophen-2-yl)-N,N-diphenylbenzenamine 
• 1431609-90-3 C₅₂H₅₂Br₂N₂S₄ 
• 1431609-83-4 5,8-bis(5-bromothiophen-2-yl)quinoxaline 
• 1100761-34-9 5,8-bis(5-bromothiophen-2-yl)-2,3-bis(3-(octyloxy)phenyl)quinoxaline 

Relevant articles and documents

Synthesis and properties of new low band gap semiconducting polymers

Low band gap organic semiconducting polymers were prepared as p-type donors for organic photovoltaic devices. A novel dibrominated monomer composed of phenothiazine, thiophene, and benzothiadiazole (DPDTBT) was synthesized as a low band gap core block. DP

Solution-processable crystalline platinum-acetylide oligomers with broadband absorption for photovoltaic cells

A series of solution-processable and crystalline platinum-acetylide oligomers containing a thienyl-benzothiadiazole-thienyl core and oligothiophene alkynyl ligands are synthesized and characterized. X-ray crystallography analysis indicates a two-dimensional arrangement of oligomers through CH- interactions in single crystals. These oligomers show two intense and broad absorption bands in the visible spectral region, with the short-wavelength absorption band being strongly dependent on the oligothiophene length. In neat films, all the oligomers form large crystalline domains of several hundred nanometers in size upon thermal treatment and exhibit space-charge limited current (SCLC) mobilities on the order of 10-5-10-4 cm2-V-1-s-1. The photovoltaic properties of these oligomers were evaluated by fabricating bulk heterojunction devices with fullerene derivatives (PC61BM and PC71BM) and some of these devices showed high-power conversion efficiencies (PCEs) of up to 3% and a peak external quantum efficiency (EQE) to 50% under AM 1.5 simulated solar illumination. The present work suggests that well-defined platinum oligomers with desirable light-absorbing and self-assembly properties have potential for solution-processed organic photovoltaics.

Synthesis and electrostatic Nano-Assembly of water-soluble Polybenzothiadiazole derivatives with long-wavelength emission in the solid states

We have synthesized APBT and APTBT containing benzothiadiazole units by Suzuki cross-coupling reaction with good yield. The polymers showed blue emission colors in aqueous solutions, while long wavelength shift was observed in the solid state due to facilitated exciton migration. APBT and APTBT are water-soluble and highly-fluorescent conjugated polymers with negatively charged sulfonate side chains and thus they can be electrostatically assembled with oppositely charged polyelectrolyte such as cationic polymer, poly(dimethyldiallylammonium chloride) (PDAC) via layerby- layer (LbL) deposition technique on a glass slide. According to the increased the number of bilayer, we found that the assembled film exhibited larger enhancement of the long wavelength emission relative to the blue emission, due to the increased excition migration. Copyright

An ultra-highly sensitive and selective self-enhanced AIECL sensor for public security early warning in a nuclear emergencyviaa co-reactive group poisoning mechanism

The worldwide application of nuclear power has created the potential risk of a nuclear accident, which has been a challenge to public security. In nuclear leakages, I2radioisotopes would cause rapid, global pollution. Therefore, highly sensitive and selective I2sensors exhibit their significance in nuclear accident early warnings and treatments. Herein, a conjugated polymer was developed for I2vapor monitoring with an ultra-low limit of detection (LOD). This polymer, modified with a tertiary amine as a co-reactive group, exhibits aggregation-induced electrochemiluminescence (AIECL) and self-enhanced ECL behaviors. It is noteworthy that the tertiary amine also acts as I2vapor capturing and sensing groups to give a LOD of 0.13 ppt. Excellent selectivity was obtained in various interfering atmospheres. A new mechanism was discovered for designing vapor sensors, which is summarized as co-reactive group poisoning (CGP). To meet the high efficiency requirement of nuclear emergency monitoring, an I2sensor modified screen printed carbon electrode was used due to its low cost, lack of need for pretreatment and suitability for mass production. A matching upwardly photosensitive ECL dark box was further designed. This study reports ECL vapor monitoring for the first time and provides a novel strategy for early warning of a nuclear emergency, suggesting its significance in environmental and public security fields.

Nonlinear Optical Studies of Conjugated Organic Dyes for Optical Limiting Applications

D-π-A conjugated organic dyes made of different donor/acceptor moieties namely Hexylcarbazole (HC), 4,7- Dithiophene-2-yl) benzo[c][1,2,5]thiadiazole (DTBT) and Poly-4-(5-(9-Hexyl-9H-carbazol-2-yl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole (PCTB) were prepared by coupling reactions. FTIR, NMR, and mass spectrometry were used to determine the molecular structure of synthesized compounds. Both HC and DTBT show a wide optical transmittance window (400-600 nm) with absorption maxima in the UV region. However, PCTB shows an altered band structure with a broad absorption in the visible domain (448 nm). Density functional theory (DFT) calculations expose that the bandgap between HOMO and LUMO decreases as the conjugation extends, and redshift occurs in UV-Vis absorption spectra. The emission spectrum of PCBT shows strong emission maxima at 541 nm with the corresponding large Stokes shift 3837 cm?1 due to its enhanced charge transfer property in the excited state. Nonlinear optical absorption was studied by open-aperture Z-scan technique using Nd:YAG laser (532 nm, 10 Hz, 9 ns). Here HC, DTBT exhibit a genuine two-photon absorption (TPA) process while PCTB possesses sequential TPA involving excited-state absorption. All dyes exhibit energy-absorbing optical limiting behaviour ascribed due to the two-photon absorption process. Among the investigated dyes, PCTB polymer shows a higher TPA coefficient (1.22 × 10?10 m/W) and a lower onset optical limiting threshold (1.06 × 1012 W/m2). Thus, the tunability of band structure and nonlinearity with a change in the molecular arrangement was successfully demonstrated in thiophene-benzothiadiazole-based organic dyes.

Synthesis of donor-acceptor-type conjugated polymer dots as organic photocatalysts for dye degradation and hydrogen evolution

Conjugated polymers (CPs) having various donor-acceptor units in the main chain were synthesized via Suzuki coupling reaction for an organic photocatalyst that can generate reactive oxygen species (ROS) for dye degradation and H2 evolution unde

Effect of thiophene/furan substitution on organic field effect transistor properties of arylthiadiazole based organic semiconductors

Four donor-acceptor (D-A) type organic semiconductors, consisting of 5-hexylthiophene with thiophene/furan flanked benzothiadiazole/naphthothiadiazole, were investigated for organic field effect transistor (OFET) application. Despite being an analogue of thiophene, furan has received less attention in organic electronics due to its dissimilar properties to thiophene and instability in photochemical oxidation. Nevertheless, this study determines that furan could display comparable charge transport properties to its analogue. The extension of the electron-accepting thiadiazole core with the benzo group and different heteroatom flanking groups were investigated to show that the performance of OFETs is dependent on the molecular orbital, geometry, and packing. Bottom-gate bottom-contact device configuration was used to study the OFET transport properties of all the molecules. We successfully proved that a furan unit is a promising building block with a mobility (μmax) of 0.0122 cm2 V-1 s-1 for devices employing furan-substituted benzothiadiazole as the channel layer.

Phenolic Bis-styrylbenzo[ c]-1,2,5-thiadiazoles as Probes for Fluorescence Microscopy Mapping of Aβ Plaque Heterogeneity

A fluorescent bis-styryl-benzothiadiazole (BTD) with carboxylic acid functional groups (X-34/Congo red analogue) showed lower binding affinity toward Aβ1-42 and Aβ1-40 fibrils than its neutral analogue. Hence, variable patterns of neutral OH-substituted bis-styryl-BTDs were generated. All bis-styryl-BTDs showed higher binding affinity to Aβ1-42 fibrils than to Aβ1-40 fibrils. The para-OH on the phenyl rings was beneficial for binding affinity while a meta-OH decreased the affinity. Differential staining of transgenic mouse Aβ amyloid plaque cores compared to peripheral coronas using neutral compared to anionic bis-styryl ligands indicate differential recognition of amyloid polymorphs. Hyperspectral imaging of transgenic mouse Aβ plaque stained with uncharged para-hydroxyl substituted bis-styryl-BTD implicated differences in binding site polarity of polymorphic amyloid plaque. Most properties of the corresponding bis-styryl-BTD were retained with a rigid alkyne linker rendering a probe insensitive to cis-trans isomerization. These new BTD-based ligands are promising probes for spectral imaging of different Aβ fibril polymorphs.

Effect of end group functionalisation of small molecules featuring the fluorene-thiophene-benzothiadiazole motif as emitters in solution-processed red and orange organic light-emitting diodes

A series of red fluorescent materials (compounds 1-4), which each contain the symmetric fluorene-thiophene-BT-thiophene-fluorene core, is presented along with their performance in solution-processed OLED devices. Extending the molecular conjugation throug

Efficient aggregated luminescent material and preparation method thereof

The invention relates to an efficient aggregated luminescent material and a preparation method thereof. The preparation method comprises the following steps: (1) Stille coupling of thienyl; (2) N-bromosuccinimide (NBS) bromination; (3) [2.2] paracycloalkane cross-coupling. The synthetic process of the luminescent material provided by the invention is simple in conditions and relatively low in preparation cost; at the same time, the luminescent material has relatively good aggregated luminescence property and optical stability, and can realize thorough application researches in stimulated emission depletion (STED) ultra-high resolution imaging.