25121-87-3

Usage

Uses

Used in Chemical Synthesis:
2,5-Dibromothieno[3,2-b]thiophene is used as a key intermediate in the synthesis of various complex organic molecules, particularly those involving fused thiophene rings. Its unique structure allows for the formation of novel compounds with potential applications in different industries.
Used in Electronic Properties:
Due to its electronic properties, 2,5-Dibromothieno[3,2-b]thiophene is used as a building block for the development of new materials with enhanced electrical conductivity, optoelectronic properties, and stability. These materials can be employed in various electronic devices, such as organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and field-effect transistors (FETs).
Used in Pharmaceutical Industry:
2,5-Dibromothieno[3,2-b]thiophene can be utilized as a starting material for the synthesis of new pharmaceutical compounds with potential therapeutic applications. Its unique structure and electronic properties may contribute to the development of novel drugs with improved efficacy and selectivity.
Used in Material Science:
In the field of material science, 2,5-Dibromothieno[3,2-b]thiophene can be used to develop new materials with tailored properties, such as improved mechanical strength, thermal stability, and chemical resistance. These materials can find applications in various industries, including aerospace, automotive, and construction.

InChI:InChI=1/C6H2Br2S2/c7-5-1-3-4(10-5)2-6(8)9-3/h1-2H

Upstream product

• 251-41-2 thieno[3,2-b]thiophene 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 

Downstream Products

• 21210-90-2 2,5-di-thiophen-2-yl-thieno[3,2-b]thiophene 
• 139896-65-4 2,5-bis[2-(trimethylsilyl)ethynyl]thieno[3,2-b]thiophene 
• 1170871-48-3 2,5-bis(4-dodecyl-5-phenylthiophen-2-yl)thieno[3,2-b]thiophene 
• 1032372-89-6 2,5-bis[2-(4-pentylphenyl)vinyl]thieno[3,2-b]thiophene 
• 84466-16-0 2,5-distyrylthieno[3,2-b]thiophene 
• 1394244-21-3 2,5-bis[2-(methylsulfinyl)phenyl]thieno[3,2-b]thiophene 
• 1381839-79-7 2,5-bis[(2-methylthio)phenyl]thieno[3,2-b]thiophene 
• 1312547-18-4 [(S)-1-((S)-2-{5-[4-(5-bromothieno[3,2-b]thiophen-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidine-1-carbonyl)-2-methylpropyl]carbamic acid methyl ester 
• 1402850-20-7 C₂₆H₁₈N₂S₂ 
• 1185221-50-4 2,5-bis(5-(4-dodecylphenyl)thiophen-2-yl)thieno[3,2-b]thiophene 
• 1422279-59-1 C₂₈H₁₄F₆S₄ 
• 1185221-51-5 2,5-di(5-phenylthiophen-2-yl)thieno[3,2-b]thiophene 
• 1281324-46-6 thieno[3,2-b]thiophene-2,5-diyldiboronic acid 

Relevant academic research and scientific papers

Charge carrier mobility study of a mesogenic thienothiophene derivative in bulk and thin films

A novel mesogenic 2,5-bis-(5-octylthiophene)-thieno[3,2b]thiophene (TT) derivative has been synthesized. The fused-ring thiophene, end-capped with two octylthiophenes, exhibits ordered lamellar mesophases which were characterized by polarizing optical microscopy, differential scanning calorimetry and small-angle X-ray diffraction at various temperatures. The charge transport properties were investigated by time-of-flight technique as a function of temperature. On cooling from isotropic phase, a maximum hole mobility value of 0.07 cm2 V-1 s-1 was measured in the highly ordered mesophase of the bulk films. Field-effect transistor experiments on both solution and vacuum deposited thin films have also been performed. The solution-processed films exhibit charge carrier mobilities several orders of magnitude lower than values extracted from bulk time-of-flight curves and from vacuum deposited thin film transistors. This work provides evidence that the melt-processing route is an efficient alternative to commonly used solution-processing for fabrication of charge transporting layers from liquid crystalline semiconductors, with performances comparable to evaporation techniques.

Synthesis and characterization of S,N-heterotetracenes

The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep synthetic routes. A Buchwald-Hartwig amination of brominated precursors, thermolysis of azide precursors, and a Cadogan reaction of nitro-substituted precursors were successfully applied to eventually build-up pyrrole rings to stable and soluble fused systems. The various obtained heteroatom sequences 'SSNS' (SN4), 'SNNS' (SN4''), and 'NSSN' (SN4') allowed for evaluation of structure-property relationships relative to the sulfur analogue tetrathienoacene ('SSSS'). In line with the results for the whole series of S,N-heteroacenes, we find that replacement of sulfur by nitrogen atoms in the tetra- and hexacyclic systems leads to a red-shift in absorption, a decrease in oxidation potential and energy gap. On the other hand, the replacement of a thiophene ring by benzene leads to the opposite effects.

Fused dithienogermolodithiophene low band gap polymers for high-performance organic solar cells without processing additives

We report the synthesis of a novel ladder-type fused ring donor, dithienogermolodithiophene, in which two thieno[3,2-b]thiophene units are held coplanar by a bridging dialkyl germanium. Polymerization of this extended monomer with N-octylthienopyrrolodione by Stille polycondensation afforded a polymer, pDTTG-TPD, with an optical band gap of 1.75 eV combined with a high ionization potential. Bulk heterojunction solar cells based upon pDTTG-TPD:PC71BM blends afforded efficiencies up to 7.2% without the need for thermal annealing or processing additives.

Rigid oligomers based on the combination of 3,6-dimethoxythieno[3,2-b]thiophene and 3,4-ethylenedioxythiophene

New oligomers based on the combination of the 3,6-dimethoxythieno[3,2-b]thiophene and 3,4-ethylenedioxythiophene (EDOT) moieties have been prepared and studied by UV-vis spectroscopy and cyclic voltammetry. The use of the intrinsically rigid thienothiophene units in addition to the S?O intramolecular interactions leads to planar conformation of the conjugated chains. While the radical cations of oligomers end capped by n-hexyl chains show a tendency to the dimerization, those substituted by n-hexylsulfanyl chains present a high stability.

Novel metal-free organic dyes containing linear planar 11,12-dihydroindolo[2,3-a]carbazole donor for dye-sensitized solar cells: Effects of π spacer and alkyl chain

Three novel D?π?A type dyes DC1～3, which consisting of indolo[2,3-a]carbazole as donor scaffold linked to the acceptor/anchoring unit cyanoacetic acid via different π-spacers, were successfully designed and synthesized. The structure, photophysical and electrochemical properties, and photovoltaic properties of the three sensitizers were investigated in detail. The results indicate that the donor 11,12-bis(2-ethylhexyl)-11,12-dihydroindolo[2,3-a]carbazole with two branched alkyl chains is effective in inhibiting the intermolecular π?π aggregation effects, and the auxiliary alkyl chains in the π-bridge cause the DC3-based DSSCs to exhibit higher open circuit voltages than that of the devices based on dye DC2. Among all of the devices fabricated with the dyes, the DC3-based cells without chenodeoxycholic acid (CDCA) exhibit the best photovoltaic performance, with a short-circuit current density of 10.98 mA cm?2, an open circuit voltage of 752 mV and a fill factor of 0.725, corresponding to a highest power conversion efficiency of 5.98% in liquid electrolyte.

Photophysical characteristics and photosensitizing abilities of thieno[3,2-b]thiophene-Based photosensitizers for photovoltaic and photocatalytic applications

Six donor?π?acceptor (D–π–A) organic dyes based on thieno[3,2-b]thiophene π-linker comprising different alkyl side chains were synthesized and characterized. Their photophysical and electrochemical properties were studied and their corresponding performances as photosensitizers (PSs) in dye-sensitized solar cells (DSSCs) and photocatalytic hydrogen production systems were also investigated. A power conversion efficiency (PCE) of 5.25 % in DSSCs and a decent H2 turnover number (TON) of 5170 (48 h) in platinized TiO2 hydrogen production system were demonstrated. The results indicated that alkyl chain engineering is one of the crucial steps in designing a superior photosensitizer.

Synthesis and Properties of C2h-Symmetric BN-Heteroacenes Tailored through Aromatic Central Cores

The 2-fold successive electrophilic borylation on one aromatic central core led to a series of C2h-symmetric BN-heteroacenes in excellent yields. For the first time, we introduced trimethylsilyl (TMS) as either leaving group or oriented group f

New fused bis-thienobenzothienothiophene copolymers and their use in organic solar cells and transistors

A new tetradodecyl-substituted DTBTBT donor unit is synthesized by a specific bis-annulation via Suzuki-Miyaura coupling and successfully incorporated into light absorbing electron donor copolymers for OPV and hole and electron transport OFET polymer devices. All copolymers (DTBTBT-co- benzothiadiazole (Bz), DTBTBT-co-thiophene (T) and DTBTBT-co-thienothiophene (TT)) show fully coplanar backbones and strong intermolecular interactions. The DTBTBT-Bz copolymer led to a deep HOMO level (-5.2 eV) and thus a large V oc value of 0.92 V with PC71BM as electron acceptor and a PCE of 3.7% with a Jsc of 6.78 mA/cm2 could be obtained. A hole mobility of 0.1 cm2/(V s) has been observed for the highly coplanar and more crystalline DTBTBT-T copolymer.

NOVEL THIENOTHIOPHENE COMPOUNDS FOR LONG-ACTING INJECTABLE COMPOSITIONS AND RELATED METHODS

The present invention provides compounds useful for the treatment of opioid dependence, alcohol dependence, alcohol use disorder, or the prevention of relapse to opioid dependence in a subject in need thereof. Related pharmaceutical compositions and methods are also provided herein.

Five-membered heterocyclic organic compound and application thereof

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a five-membered heterocyclic organic compound and application thereof. The organic compoundprovided by the invention has a five-membered heterocyc