1295502-53-2

Basic information

• Product Name: 4,7-dibroMo-5,6-difluorobenzo[c][1,2,5]thiadiazole
• Synonyms: 4,7-Dibromo-5,6-difluoro-benzo[1,2,5]thiadiazole;4,7-dibroMo-5,6-difluorobenzo[c][1,2,5]thiadiazole;5,6-difluoro-4,7-dibroMobenzo[c][1,2,5]thiadiazole;4,7-Dibromo-5,6-difluoro-2,1,3-benzothiadiazole;2,1,3-Benzothiadiazole, 4,7-dibromo-5,6-difluoro-;BT2F-2Br
• CAS NO: 1295502-53-2
• Molecular Formula: C₆Br₂F₂N₂S
• Molecular Weight: 329.9474064
• EINECS: -0
• Mol File: 1295502-53-2.mol

Chemical Properties

• Melting Point: 153.0 to 157.0 °C
• Boiling Point: 318.2±37.0 °C(Predicted)
• Flash Point: >300℃
• Appearance: /
• Density: 2.352±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -5.16±0.50(Predicted)
• CAS DataBase Reference: 4,7-dibroMo-5,6-difluorobenzo[c][1,2,5]thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-dibroMo-5,6-difluorobenzo[c][1,2,5]thiadiazole(1295502-53-2)
• EPA Substance Registry System: 4,7-dibroMo-5,6-difluorobenzo[c][1,2,5]thiadiazole(1295502-53-2)

Safety Data

• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 1295502-53-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Semiconductor Synthesis:
4,7-dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole is used as a building block for the synthesis of fluorinated benzothiadiazole-based conjugated polymers. The incorporation of this monomer into low-band gap polymer semiconductors introduces better electron affinity and further lowers the band gap of the semiconducting materials, making it suitable for applications in organic photovoltaics and light-emitting diodes.
Used in Organic Photovoltaics:
In the photovoltaic industry, 4,7-dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole is used as a key component in the development of high open-circuit voltage materials. The electron-withdrawing nature of the compound, due to the extra fluorine atoms on the benzothiadiazole ring, contributes to the improved performance of organic photovoltaic devices by enhancing their open-circuit voltage.
Used in Light-Emitting Diodes (LEDs):
4,7-dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole is also utilized in the production of light-emitting diodes. The compound's electron-withdrawing properties and its ability to lower the band gap of semiconducting materials make it an essential component in the development of high-performance LEDs with improved efficiency and brightness.

Upstream product

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

Downstream Products

• 1345627-73-7 3,6-dibromo-4,5-difluoro-1,2-phenylenediamine 
• 1293389-31-7 5,6-difluoro-4,7-bis-(5-bromo-4-(2-ethylhexyl)-2-thienyl)-2,1,3-benzothiadiazole 

Relevant articles and documents

Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.

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.

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.

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.

Boron compound

PROBLEM TO BE SOLVED: To provide a method for producing a boron compound represented by a formula (II) from a compound represented by a formula (I) in a short reaction time with good yield.SOLUTION: There is provided a method for producing a boron compound represented by a formula (II), the method comprising: a step of producing a first intermediate obtained by reacting a compound represented by a formula (I) and a lithium amide compound or an alkyllithium compound and a second intermediate from the first intermediate; and a step of reacting the second intermediate and an alcohol or a divalent carboxylic acid. (I) (II) [Y represents a divalent group; and Y represents a boric acid ester residue.]

POLYMER COMPOUND

The invention relates to a polymer compound. A photoelectric conversion device that contains the polymer compound having a structural unit represented by formula (1) has high photoelectric conversion efficiency. (wherein, X1 and X2 are the same or different and represent a nitrogen atom or -CH-. Y1 represents a sulfur atom, an oxygen atom, a selenium atom, -N(R1)- or -CR2-CR3-. R1, R2 and R3 are the same or different and represent a hydrogen atom or a substituent. W1 represents a cyano group, a monovalent organic group having a fluorine atom or a halogen atom. W2 represents a cyano group, a monovalent organic group having a fluorine atom, a halogen atom or a hydrogen atom.

Compound used for forming high-molecular compound

The present invention provides a macromolecular compound by which the short-circuit current density and the photoelectric conversion efficiency are enhanced when the macromolecular compound is used in an organic layer contained in a photovoltaic cell. Specifically, the present invention provides a macromolecular compound having a structural unit represented by Formula (5): wherein R52 and R53 are the same as or different from each other and represent hydrogen atoms, halogen atoms, alkyl groups, alkyl oxygen radicals, alkyl sulfonium, aryl groups, aryl oxygen radicals, aryl sulfonium, aryl alkyl, aryl alkyl oxygen radicals, acyl groups, acyloxy, acylamino, imide groups, amidogen, substituted amino, substituted silicyl, substituted silicon alkyl oxygen radicals, substituted silicon alkyl harvard, silicon alkyl amine, univalent heterocyclic radical, heterocyclic oxygen radicals, heterocyclic sulfonium, aryl alkenyl, aryl alkynyl, carboxyl or cyan; W1 and W2 are the same as or different from each other and represent hydrogen atoms, halogen atoms, alkyl sulfonate base, aryl sulfonic acid ester base, aryl alkyl sulfonate base, boric acid ester residues, matte methyl, scales base, Phosphonic acid ester methyl, single halogenated methyl, boric acid residues, formyl groups, vinyl or organic tin residues.

METHOD FOR MANUFACTURING BORON COMPOUND

PROBLEM TO BE SOLVED: To provide a method for manufacturing a boron compound represented by the formula (II) from a compound represented by the formula (I) as a monomer providing a repeating unit of a polymer compound used for an organic thin film solar cell at a good yield. SOLUTION: There is provided a method for manufacturing a boron compound represented by the formula (II) by reacting a compound represented by the formula (I), a diboric acid ester derivative and a metal catalyst. In the formulae (I) and (II), Y represents a bivalent group, Y in both formulae are the same, and W1 and W2 represent each independently a boric acid ester residue. COPYRIGHT: (C)2015,JPOandINPIT

Structural variation of donor-acceptor copolymers containing benzodithiophene with bithienyl substituents to achieve high open circuit voltage in bulk heterojunction solar cells

Three new donor-acceptor copolymers P1, P2, and P3 were synthesized with benzodithiophene with bithienyl substituents as the donor and 5,6-difluorobenzo[c][1,2,5]thiadiazole, 4,7-di(thiophen-2-yl)benzo[c][1,2,5] thiadiazole, and 5,6-difluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole as the acceptors, respectively. The insertion of thiophene spacer between the donor and the acceptor broadened the absorption of the polymers P2 and P3 and resulted in a red shift of ～30 nm as compared to that of the polymer P1. However, the inclusion of fluorine atoms on the polymer had detrimental effects on the photovoltaic properties of the polymers. The synthesized donor-acceptor polymers were tested in bulk heterojunction (BHJ) solar cells with [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) acceptor. Polymer P2 gave a PCE of 3.52% with PC71BM in which the active layer was prepared in chloroform with 3% v/v 1,8-diiodooctane (DIO) additive. The effect of fluorine substitution and thiophene group insertion on the UV/Vis absorbance, photovoltaic performances, morphology, and charge carrier mobilities for the polymers are discussed.