17821-75-9

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
5-Fluorobenzo[2,1,3]thiadiazole is utilized as a key component in the development of pharmaceuticals due to its demonstrated biological activities. Its anticancer properties make it a candidate for the creation of new drugs targeting various types of cancer, while its antiviral properties suggest potential applications in treatments for viral infections.
Used in Organic Electronics:
Leveraging its electronic and optoelectronic properties, 5-Fluorobenzo[2,1,3]thiadiazole is employed as a material in the field of organic electronics. It contributes to the development of devices such as organic light-emitting diodes (OLEDs) and organic solar cells, enhancing their performance and efficiency.
Used in Materials Science:
In materials science, 5-Fluorobenzo[2,1,3]thiadiazole is used as a building block for synthesizing new materials with tailored properties. Its incorporation into materials can lead to advancements in areas such as polymer science, where it may improve the stability, conductivity, or other characteristics of the resulting materials.
Used in Chemical Synthesis:
As a versatile intermediate, 5-Fluorobenzo[2,1,3]thiadiazole is used in the synthesis of a wide range of organic compounds. Its reactivity and structural features make it a valuable component in creating complex molecules for various applications, from pharmaceuticals to specialty chemicals.

Upstream product

• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 2369-11-1 5-fluoro-2-nitroaniline 
• 222851-56-1 N-phenylsulfinylamine 
• 364-78-3 2-nitro-4-fluoroaniline 

Downstream Products

• 1347736-74-6 4,7-dibromo-5-fluoro-benzo[c][1,2,5]thiadiazole 
• 1402460-83-6 4-bromo-5-fluoro-7-(5'-hexyl-[2,2'-bi-thiophene]-5-yl)benzo[c][1,2,5]thiadiazole 
• 1402411-12-4 4,4'-(5',5'''-(5-fluorobenzo[c][1,2,5]thiadiazole-4,7-diyl)bis([2'',2'''-bithiophene]-5'',5'-diyl))bis(N,N-diphenylaniline) 
• 1557036-91-5 1-(4-(5-fluorobenzo[c][1,2,5]thiadiazol-4-yl)phenyl)ethanone 
• 1347736-83-7 3,6-dibromo-4-fluoro-1,2-phenylenediamine 
• 1452404-93-1 5-fluoro-4,7-diphenylbenzo[c][1,2,5]thiadiazole 
• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 

Relevant academic research and scientific papers

Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications

A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were performed on model tetramer structures to shed light on how substituting the fluorine atom to the acceptor building block affects the structural, electronic and optical properties of the polymers. The results of computational studies were compared with experimental studies. The structure adjustment accomplished by fluorine substitution on the benzothiadiazole moiety reveals an influence on the electronic structure of polymers with a more negative HOMO energy level. A high VOC for the resulting photovoltaic device was examined for PBDTSe-FFBT. Difluorinated polymer PBDTSe-FFBT:PC71BM organic solar cell exhibited the highest photovoltaic performance of 2.63% with JSC of 7.24 mA cm-2, VOC of 0.72 V and FF of 50.6%. PBDTSe-BT:PC71BM revealed the best PCE as 2.39%, and the device reached the highest efficiency up to 1.68% for PBDTSe-FBT:PC71BM.

Chlorination: Vs. fluorination: A study of halogenated benzo [c] [1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging

Red/near-infrared organic dyes are becoming increasingly widespread in biological applications. However, designing these dyes with long-wavelength emission, large Stokes shifts, and high fluorescence quantum efficiency is still a very challenging task. In this work, five donor-acceptor (D-A) red/near-infrared fluorophores based on different chlorinated/fluorinated benzo[c][1,2,5]thiadiazole units are designed and synthesized. The photophysical, theoretical calculations, and electrochemical properties explored in this study have proved that the introducing of chlorine atoms will lead to a lower HOMO level, stronger steric hindrance, and a relatively lower quantum yield in solutions. When the organic dots are fabricated, the chlorinated dots demonstrate much higher fluorescence quantum yield, larger Stokes shift, and better photostability than that of the fluorinated dots. After labeling A549 cells, all the chlorinated/fluorinated dots exhibit high red emission intensities. All these results indicated that the subtle change in the halogen atom of the benzo[c][1,2,5]thiadiazole unit is a unique method to tune the photophysical properties of those materials, and also provides good guidelines to design highly efficient red/near-infrared molecules for cellular imaging applications.

INERT SOLUTION-PROCESSABLE MOLECULAR CHROMOPHORES FOR ORGANIC ELECTRONIC DEVICES

Small organic molecule chromophores containing a benzo[c][1,2,5]thiadiazole with an electron-withdrawing substituent W in the 5-position (5BTH), benzo[c][1,2,5]oxadiazole with an electron-withdrawing substituent W in the 5-position (5BO), 2H-benzo[d][1,2,3]triazole (5BTR) with an electron-withdrawing substituent W in the 5-position (5BTR), 5-fluorobenzo[c][1,2,5]thiadiazole (FBTH), 5-fluorobenzo[c][1,2,5]oxadiazole (FBO), or 5-fluoro-2H-benzo[d][1,2,3]triazole (FBTR) core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

Effective design of A-D-A small molecules for high performance organic solar cells via F atom substitution and thiophene bridge

Three novel small molecules with acceptor-donor-acceptor (A-D-A) configuration, SBDT1, SBDT2 and SBDT3, where 4,8-bis(octyloxy)benzo[1,2-b:4,5-b′]dithiophene (BDT) as the electron-donating core connecting to thiophene-substituted benzothiadiazole (BT) as electron-withdrawing are reported. The effects of fluorine atoms on the photophysical properties by introducing different fluorine atoms into the benzothiadiazole unit were investigated. These SBDTs exhibit good thermal stability, excellent panchromatic absorption in solution and film. SBDT2 and SBDT3 with fluorine-substituted BT possess a relatively deeper the highest occupied molecular orbital (HOMO). These A-D-A type molecules were treated as donor and PC71BM as acceptor in bulk heterojunction (BHJ) small-molecule organic solar cells (SMOSCs). Among them, device based on SBDT2 gave the best device performance with a PCE of 5.06% with Jsc of 10.56 mA/cm2, Voc of 0.85 V, fill factor (FF) of 56.4%. These studies indicate that proper incorporation of fluorine atoms is an effective way to increase the efficiency of organic solar cells.

(AZA)INDOLE-, BENZOTHIOPHENE-, AND BENZOFURAN-3-SULFONAMIDES

Disclosed are sulfonamide compounds with GPR17 modulating properties, which are useful for treating or preventing a variety of CNS and other diseases, in particular for preventing and treating myelinating diseases or disorders.

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki-Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution. Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.

FUSED RING DERIVATIVE AND ORGANIC SOLAR CELL COMPRISING THE SAME

The present invention relates to a condensed cyclic derivative represented by chemical formula 1, and an organic solar cell containing the same. According to an embodiment of the present invention, the condensed cyclic derivative exhibits excellent coating properties by having a hydroxyl group, an alkyl group, an alkoxy group, and a sulfide group as a substituent.COPYRIGHT KIPO 2017

Syntheses and photovoltaic properties of 6-(2-thienyl)-4H-thieno[3,2-b]indole based conjugated polymers containing fluorinated benzothiadiazole

In this report, a series of copolymers based on 6-(2-thienyl)-4H-thieno[3,2-b]indole (TTI) as an electron-rich unit and fluorinated DTBT as an electron-deficient unit were synthesized, namely PTTIF1 and PTTIF2, and applied to photovoltaic devices. TTI unit was coupled with fluorinated DTBT to utilize the merit of introduction of fluorine atom leading to the lowering of the HOMO energy level while keeping high planarity of the conjugated backbone. The synthesized copolymers show a noticeable change in HOMO energy levels as compared with non-fluorinated polymer (PTTIDTBT-h). Optimized photovoltaic devices of PTTIF2 exhibited power conversion efficiency of 4.36% with decent JSC and FF values, which can be explained by the higher charge transporting ability of PTTIF2 with preferable face-on crystallite population than PTTIF1 in grazing incident wide-angle X-ray scattering (GIWAXS).

Facile synthesis of fluorine-substituted benzothiadiazole-based organic semiconductors and their use in solution-processed small-molecule organic solar cells

A facile new protocol for the synthesis of iodinated derivatives of fluorinated benzothiadiazoles is demonstrated for the production of p-type semiconducting materials. The newly synthesized small-molecule compounds bis[TPA-diTh]-MonoF-BT and bis[TPA-diTh]-DiF-BT exhibited a power conversion efficiency of 2.95 % and a high open-circuit voltage of 0.85 V in solution-processed small-molecule organic solar cells. A facile new protocol was developed for synthesis of iodinated derivatives of fluorinated benzothiadiazoles as precursors for fluorine-substituted benzothiadiazole-based organic semiconductors 2 and 3, which exhibit enhanced intramolecular charge transfer compared to unfluorinated analogue 1 and hence improved photovoltaic performance in small-molecule organic solar cells (see figure). Copyright

Facile synthesis of fluorine-substituted benzothiadiazole-based organic semiconductors and their use in solution-processed small-molecule organic solar cells

A facile new protocol for the synthesis of iodinated derivatives of fluorinated benzothiadiazoles is demonstrated for the production of p-type semiconducting materials. The newly synthesized small-molecule compounds bis[TPA-diTh]-MonoF-BT and bis[TPA-diTh]-DiF-BT exhibited a power conversion efficiency of 2.95 % and a high open-circuit voltage of 0.85 V in solution-processed small-molecule organic solar cells. A facile new protocol was developed for synthesis of iodinated derivatives of fluorinated benzothiadiazoles as precursors for fluorine-substituted benzothiadiazole-based organic semiconductors 2 and 3, which exhibit enhanced intramolecular charge transfer compared to unfluorinated analogue 1 and hence improved photovoltaic performance in small-molecule organic solar cells (see figure). Copyright