98057-08-0

Basic information

• Product Name: 5,5''-dibromo-[2,2':5',2"]terthiohene
• Synonyms: 2,5-Bis(5-bromothiophen-2-yl)thiophene;5,5μμ-Dibromo-2,2μ:5μ,2μμ-terthiophene;2,5-Bis(5-broMo-2-thienyl)thiophene;5,5''-Dibromo-alpha-terthienyl;5,5''-Dibromo-2,2':5',2''-terthiophene 97%;5',2"]terthiohene;5,5''-dibromo-[2,2';5',2"]ter
• CAS NO: 98057-08-0
• Molecular Formula: C₁₂H₆Br₂S₃
• Molecular Weight: 406.185
• Product Categories: Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Materials Science;Organic and Printed Electronics;Synthetic Tools and Reagents;Thiophene Monomers and Building Blocks;Thiophenes
• Mol File: 98057-08-0.mol

Chemical Properties

• Melting Point: 150-155 °C
• Boiling Point: 417.2°Cat760mmHg
• Flash Point: 206.1°C
• Appearance: /
• Density: 1.839
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 5,5''-dibromo-[2,2':5',2"]terthiohene(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5''-dibromo-[2,2':5',2"]terthiohene(98057-08-0)
• EPA Substance Registry System: 5,5''-dibromo-[2,2':5',2"]terthiohene(98057-08-0)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41
• Safety Statements: 26-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 98057-08-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics:
5,5''-dibromo-[2,2':5',2"]terthiohene is used as a building block for the synthesis of conjugated polymers and organic semiconductors due to its high thermal stability and unique electronic properties. These polymers and semiconductors are essential components in various electronic devices, such as organic light-emitting diodes (OLEDs), field-effect transistors (FETs), and sensors.
Used in Optoelectronic Devices:
In the optoelectronics industry, 5,5''-dibromo-[2,2':5',2"]terthiohene is used as a precursor for the development of materials with tailored electronic and optical properties. Its incorporation into optoelectronic devices can enhance their performance, such as in OLEDs and photovoltaic cells, by improving charge transport and light absorption characteristics.
Used in Organic Photovoltaics:
5,5''-dibromo-[2,2':5',2"]terthiohene is used as a component in the development of organic photovoltaic materials. Its unique electronic properties and high thermal stability contribute to the efficiency and durability of solar cells, making it a promising candidate for the advancement of renewable energy technologies.
Used in Cross-Coupling Reactions:
In the field of organic synthesis, 5,5''-dibromo-[2,2':5',2"]terthiohene serves as a useful precursor in cross-coupling reactions for the formation of more complex organic molecules. The presence of bromine atoms allows for efficient coupling with other organic compounds, enabling the synthesis of a wide range of molecules with diverse applications in materials science, pharmaceuticals, and other industries.

Upstream product

• 1081-34-1 2,2':5',2''-terthiophene 

Downstream Products

• 5660-45-7 quinquethienyl 
• 13130-50-2 2,5-bis(5-formylthiophen-2-yl)thiophene 
• 1402850-22-9 C₃₂H₂₂N₂S₃ 
• 1404575-89-8 5,5''-bis((4vinylphenyl)ethynyl)-2,2':5'2''-terthiophene 
• 331472-71-0 C₄₀H₃₄N₂O₄S₃ 
• 1333308-12-5 C₈₆H₁₂₆N₂O₆S₅ 
• 1333308-08-9 C₁₀₈H₁₇₀N₂O₈S₅ 
• 1172120-73-8 5-(5'-(5''-bromothiophen-2''-yl)thiophen-2'-yl)-2-(diphenylamino)thiophene 
• 1172120-72-7 5-(5'-(5''-bromothiophen-2''-yl)thiophen-2'-yl)-2-(1-naphthyl(phenyl)amino)thiophene 

Relevant articles and documents

Tuning photoluminescent wavelength of water-soluble oligothiophene/polymer complex film by proton bonding

We synthesized a new oligothiophene derivative with pyridine end groups and investigated their optical properties. Upon adding an aqueous polystyrene sulfonic acid solution, it forms homogeneous polymer complex films with protonated structure. Furthermore

Relationship between the energy levels and the photovoltaic properties of oligothiophenes

A series of linear π-conjugated oligothiophenes, α,α'- dihexylquinquethiophene (DH5T), 2,5-bis(5'-hexyl-2,2'-bithiophene-5-yl)thieno[3, 2-b]thiophene (DH5TT), and α, α'-dihexylheptathiophene (DH7T), has been synthesized using the Suzuki coupling reaction. The optical and electrochemical properties of oligothiophenes were easily tuned by controlling the thiophene number. The UV-vis absorption and photoluminescence (PL) spectra are gradually red-shifted on going from DH5T and DH5TT to DH7T due to the increase in α-conjugation length. The energy band gap decreased as the oligothiophene length increased. The optical band gaps of DH5T, DH5TT, and DH7T occur at 2. 39, 2.25, and 2.01 eV, respectively. Bulk heterojunction organic photovoltaic cells (OPVs) fabricated from oligomers showed the power conversion efficiency of 0.45-0.8% under AM 1.5 (100 mW/cm2). Among them, DH5T showed the best OPV performance of an open circuit voltage (VOC) of 0.51 V, short-circuit current (JSC) of 4.25 mA/cm2, and fill factor (FF) of 0.37, resulting in the power conversion efficiency of 0.80%. Moreover, the relationship between conjugation length and photovoltaic properties was systematically investigated in terms of the energy band gap and open circuit voltage (VOC). Copyright

PROCESS FOR PRODUCTION OF OXIDATION REACTION PRODUCT OF AROMATIC COMPOUND

The present invention provides a process for producing an oxidation reaction product of an aromatic compound, having excellent environmental load reduction performance, cost reduction performance, etc. Provided is a process for producing an oxidation reaction product of a raw material aromatic compound by reacting the raw material aromatic compound with an oxidizing agent. The process further uses an electron donor-acceptor linked molecule. The process includes the step of: reacting the electron donor-acceptor linked molecule in an electron-transfer state, the oxidizing agent, and the raw material aromatic compound, thereby generating an oxidation reaction product resulting from oxidation of the raw material aromatic compound.

A novel method for the bromination of thiophenes

A novel, fast and convenient method for the bromination of thiophenes and oligothiophenes with N-bromosuccinimide (NBS) using ultrasonic irradiation is elaborated. The yield of bromothiophenes strongly depends on the initial thiophene structure and nature of the solvent.

Synthesis and photovoltaic properties of formyl end-capped oligothiophenes

For the purpose of developing novel photovoltaic materials, 5,5″-biformyl-2,2′:5′,2″-terthiophene (OHC-3T-CHO) and 5,5″-biformyl-2,2′:5′,2″:5″,2?:5?, 2″″-q-uinquethiophene (OHC-5T-CHO) were synthesized. The photovoltaic properties of OHC-3T-CHO and OHC-5T-CHO were studied. We have fabricated two flexible organic photovoltaic devices using OHC-3T-CHO, OHC-5T-CHO, and 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA). The PET-ITO (indium tin oxides coated with polyethylene terephthalate)/OHC-3T-CHO/ PTCDA/Al device has an open circuit voltage (Voc) of 1.12V, and photoelectric conversion efficiency (PCE) of 1.00%, whereas the PET-ITO/OHC-5T-CHO/PTCDA/Al device has a Voc of 1.78V and PCE of 1.08%. Both devices have high Voc (1.12V and 1.78V). It is possible that intermolecular hydrogen bonding between the -CHO group of OHC-nT-CHO and the carboxylic dianhydride of PTCDA enhanced the efficiency by promoting forward interfacial electron transfer.

Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives

In order to develop novel oligothiophene-based liquid crystals capable of hydrogen bonding, new terthiophene derivatives containing an alkylamide group, N,N′-dialkyl-5,5″-dichloro-2,2′:5′,2″- terthiophene-4,4″-dicarboxamide (DNCnDCl3T, n=8, 18)

Synthesis of extended α,α'-oligo(silylthiophenes) by cerium(IV) oxidative coupling reactions

Cerium(IV) oxidative dimerisations of 4,4'-bis(trimethylsilyl)-2,2':5',2''-terthiophene and the quaterthienyl analogue 1c gave the corresponding sexi- and octi-thiophenes; the latter have been used to prepare α-linked hexadecithiophene and tetracosithiophene derivatives.

Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds

We have synthesized and characterized a series of novel compounds of α,α'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are α,α'-bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopenthyl)methyl] oligothiophene, α,α'-bis(aminomethyl)oligothiophene dihydrochloride and α,α'- bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example α,α'-bis(aminomethyl)oligothiophene dihydrochloride is soluble in water. The results of electronic spectra and duration are also presented.

Preparation of extended di(4-pyridyl)thiophene oligomers

Different methods for the coupling of 2-(4-pyridyl)thiophene to α-dibrominated thiophene oligomers and their efficiency to produce a homologous series of extended di(4-pyridyl)thiophene oligomers have been studied. The coupling was found to be most efficient with the organozinc derivative of 2-(4-pyridyl)thiophene, using a Pd(dppf) complex as the catalyst in the coupling reaction. The resulting compounds are promising new models for trans-membrane molecular conductors.