1293389-29-3

Usage

Uses

Used in Organic Synthesis:
5,6-difluoro-4,7-diiodobenzo[c][1,2,5]thiadiazole is utilized as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its presence in the molecular structure can influence the reactivity and selectivity of reactions, making it a valuable component in the synthesis of pharmaceuticals and specialty chemicals.
Used in Materials Science:
In the field of materials science, 5,6-difluoro-4,7-diiodobenzo[c][1,2,5]thiadiazole is employed as a component in the development of advanced materials. Its unique structural features contribute to the properties of these materials, such as their electronic, optical, or mechanical characteristics, which can be tailored for specific applications in industries like electronics, energy, and nanotechnology.
Used in Pharmaceutical Development:
5,6-difluoro-4,7-diiodobenzo[c][1,2,5]thiadiazole is also used as a building block in the design and synthesis of new pharmaceuticals. Its heterocyclic nature allows for the creation of novel drug candidates with potential therapeutic applications, as its structure can be modified to target specific biological pathways or receptors.
Used in Research and Development:
5,6-difluoro-4,7-diiodobenzo[c][1,2,5]thiadiazole serves as a subject of ongoing research to explore its potential uses and applications across various scientific and industrial fields. Researchers are investigating its chemical properties, reactivity, and compatibility with other materials to unlock new possibilities for its utilization in innovative technologies and products.

Upstream product

• 76179-40-3 2-amino-4,5-difluoroaniline 

Downstream Products

• 1421762-30-2 5,6-difluoro-4,7-bis(5-(trimethylstannyl)thiophene-2-yl)benzo[c][1,2,5]thiadiazole 
• 1293389-31-7 5,6-difluoro-4,7-bis-(5-bromo-4-(2-ethylhexyl)-2-thienyl)-2,1,3-benzothiadiazole 
• 1283598-36-6 4,7-bis(5-bromo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole 
• 1450590-76-7 4,7-di(4-hexyl-5-bromothiophen-2-yl)-5,6-difluorine-2,1,3-benzothiadiazole 
• 1402411-13-5 4,4'-(5',5'''-(5,6-difluorobenzo[c][1,2,5]thiadiazole-4,7-diyl)bis([2'',2'''-bithiophene]-5'',5'-diyl)) 
• 1304773-89-4 4,7-bis(5-bromothiophen-2-yl)-5,6-difluorobenzo[c]-[1,2,5]thiadiazole 

Relevant academic research and scientific papers

5-alkyloxy-6-fluorobenzo[c][1,2,5]thiadiazole- and silafluorene-based D-A alternating conjugated polymers: Synthesis and application in polymer photovoltaic cells

Three donor-acceptor (D-A) alternating conjugated polymers with silafluorene as the donor unit, 5-alkyloxy-6-fluorobenzothiadiazole as the acceptor unit, and thiophene as the spacer has been synthesized and used as donor materials for polymer solar cells (PSCs). The introduction of a fluorine atom on the benzothiadiazole unit can lower the HOMO and LUMO energy level of the resulted polymers to afford higher open circuit voltage (Voc); whereas the introduction of a flexible alkyloxy chain on benzothiadiazole unit can increase the solubility of the resulted polymers without interfering the close packing of polymer chains in the solid state. High molecular weight polymers P-1a, P-1b, and P-1c, which are fully soluble in 1,2-dichorobenzene (DCB) at elevated temperature, have been prepared by Suzuki polycondensation. Among these polymers, P-1c exhibited the highest hole mobility up to 1.36 × 10-2 cm2 V-1 s-1. PSCs based P-1b:PC71BM demonstrated the highest Voc up to 0.98 V. P-1a:PC71BM based PSCs gave the highest power conversion efficiency (PCE) of 6.41%, which is the highest value among solar cells with benzothiadiazole- and silafluorene-containing polymers as the donor material.

5,6-Difluorobenzothiadiazole and silafluorene based conjugated polymers for organic photovoltaic cells

To achieve 5,6-difluorobenzothiadiazole and 2,7-linked silafluorene based soluble conjugated polymers, flexible side chains were attached at different positions of the conjugated polymers. Three soluble polymers PSiF-D(OT)DFBT, PSiF-TTDFBT, and PDOSiF-DTDFBT were prepared and used as donor materials for polymer solar cells. PSiF-D(OT)DFBT exhibits a band gap of 2.06 eV with a deep HOMO of -5.64 eV. PSiF-TTDFBT shows a band gap of 1.75 eV with the HOMO of -5.23 eV. PDOSiF-DTDFBT is of a band gap of 1.86 eV with the HOMO level of -5.37 eV. Among these three polymers, PDOSiF-DTDFBT shows the highest field effect transistor (FET) hole mobility up to 3.31 × 10-2 cm2 V-1 s-1, PDOSiF-DTDFBT:PC71BM blend films show the highest SCLC mobility up to 5.10 × 10-4 cm2 V-1 s-1, and polymer solar cells (PSCs) with the blend of PDOSiF-DTDFBT:PC71BM (1:1, by weight) as the active layer gave a power conversion efficiency (PCE) of 4.03% with an open circuit voltage (V oc) of 0.73 V, a short circuit current (Jsc) of 8.55 mA cm-2, and a fill factor (FF) of 0.65. Our studies also reveal the structure-property relationship of 2,7-linked silafluorene and 5,6-difluorobenzothiadiazole based conjugated polymers.

ELECTRONIC DEVICES USING ORGANIC SMALL MOLECULE SEMICONDUCTING COMPOUNDS

Small organic molecule semi-conducting chromophores containing a halogen-substituted core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

Fluorinated benzothiadiazole-based conjugated polymers for high-performance polymer solar cells without any processing additives or post-treatments

Thanks to their many favorable advantages, polymer solar cells exhibit great potential for next-generation clean energy sources. Herein, we have successfully designed and synthesized a series of new fluorinated benzothiadiazole-based conjugated copolymers PBDTTEH-DT HBTff (P1), PBDTTEH-DTEHBTff (P2), and PBDTHDO-DTHBTff (P3). The power conversion efficiencies of 4.46, 6.20, and 8.30% were achieved for P1-, P2-, and P3-based devices within ～100 nm thickness active layers under AM 1.5G illumination without any processing additives or post-treatments, respectively. The PCE of 8.30% for P3 is the highest value for the reported traditional single-junction polymer solar cells via a simple fabrication architecture without any additives or post-treatments. In addition, it is noteworthy that P3 also allows making high efficient polymer solar cells with high PCEs of 7.27 and 6.56% under the same condition for ～200 and ～300 nm thickness active layers, respectively. Excellent photoelectric properties and good solubility make polymer P3 become an alternative material for high-performance polymer solar cells.

Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7% efficiency

High-powered polymer: Fluorinated benzothiadiazole was incorporated into a polymer that was used in a high-performance solar cell. The model polymer 2 has decreased HOMO and LUMO energy levels and a similar band gap when compared with its nonfluorinated analogue 1. A bulk heterojunction device derived from 1 demonstrated a high power conversion efficiency of 7.2% (5.0% for 1). (Chemical Equation Presented).