1193-69-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,5-Dibromothiophene-3-carbaldehyde is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, playing a crucial role in the development of new drugs and pesticides. Its unique chemical structure allows for the creation of a wide range of compounds with potential therapeutic and pesticidal properties.
Used in Organic Light Emitting Diodes (OLEDs) Production:
In the electronics industry, 2,5-Dibromothiophene-3-carbaldehyde is employed in the production of organic light emitting diodes (OLEDs). Its chemical properties make it suitable for use in the fabrication of these devices, which are known for their high efficiency, low power consumption, and thin, flexible form factors.
Used in Organic Photovoltaic Devices:
2,5-Dibromothiophene-3-carbaldehyde also finds application in the manufacturing of organic photovoltaic devices. Its incorporation into these devices can enhance their performance and contribute to the development of more efficient and sustainable solar energy technologies.
Safety Considerations:

Upstream product

• 57846-06-7 2,5-dibromo-3-dibromomethylthiophene 
• 161490-95-5 (2,5-dibromothiophen-3-yl)methanol 
• 13191-37-2 2,5-dibromo-3-bromomethylthiophene 
• 616-44-4 3-Methylthiophene 
• 13191-36-1 2,5-dibromo-3-methylthiophene 
• 498-62-4 3-thiophene carboxaldehyde 

Downstream Products

• 208348-06-5 4'-{4-[2-(2,5-dibromothiophen-3-yl)-vinyl]phenyl}-2,2':6'2''-terpyridine 
• 634602-06-5 trans-1-((2',2'':5'',2'''-terthiophen)-3''-yl)-2-(4''''-methoxyphenyl)ethene 
• 398507-94-3 4'-[4-(2,5-dibromothiophen-3-yl-methoxymethyl)phenyl]-2,2':6',2''-terpyridine 
• 18792-01-3 2,5-dibromothiophene-3-carbonitrile 
• 1386277-86-6 (CH₃(C₆H₄)S)(C₄HSBr)C(C₄HN(CH₃)2)2BF₂ 
• 1385822-46-7 ((CH₃)(C₆H₄)S(O))2(C₄HS)CHO 
• 1385822-47-8 ((CH₃)(C₆H₄)SO₂)(C₄HS)(CHO)S(O)(C₆H₄)CH₃ 
• 1385822-48-9 ((CH₃)(C₆H₄)SO₂)2(C₄HS)CHO 
• 1386277-80-0 ((CH₃)(C₆H₄)S(O))2(C₄HS)C(C₄HN(CH₃)2)2BF₂ 
• 1386277-82-2 ((CH₃)(C₆H₄)SO₂)((CH₃)(C₆H₄)SO)(C₄HS)C(C₄HN(CH₃)2)2BF₂ 
• 1386277-83-3 ((CH₃)(C₆H₄)SO₂)2(C₄HS)C(C₄HN(CH₃)2)2BF₂ 

Relevant academic research and scientific papers

Synthesis and photovoltaic properties of copolymers based on benzo[1,2- b:4,5- b ′]dithiophene and thiophene with different conjugated side groups

Three novel copolymers (PT-ID, PT-DTBT, and PT-DTBTID) of benzo[1,2-b:4,5-b′]dithiophene and thiophene with different conjugated side groups (1,3-indanedione (ID), 4,7-dithien-5-yl-2,1,3-benzodiathiazole (DTBT), and DTBT-ID) were synthesized and developed for polymer solar cell applications. The effects of the different conjugated side groups on the thermal, photophysical, electrochemical and photovoltaic properties of these copolymers were investigated. As the length of the conjugated side groups increased, the absorption of the UV-vis region in solution was red-shifted. By changing the different side groups, the energy levels and band gaps of the resulted copolymers were effectively tuned. The three copolymers exhibit deep HOMO energy level and relatively high open-circuit voltage (Voc). Bulk heterojunction solar cells with these copolymers as electron donors and (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM) as an electron acceptor exhibit power conversion efficiencies of 2.48%, 4.18% and 1.16% for PT-ID, PT-DTBT, and PT-DTBTID, respectively.

A novel terthienyl based polymer electrochrome with peripheral BODIPY

Design, synthesis and electropolymerization of a new hybrid material based on terthienyl system bearing BODIPY appendage are reported. This electrochemically polymerized unique combination readily gives an electrochromic polymer with a narrow optical band gap (1.71 eV). The electrochrome exhibits purple color when neutralized and sky blue color when oxidized in a monomer-free electrolyte solution containing 0.1 M tetrabutylammonium tetrafluoroborate dissolved in acetonitrile. Spectroscopic and electrochemical features of the electroactive polymer electrochrome indicate that it is a promising candidate for electrochromic device and display applications.

Dye-Incorporated Polynaphthalenediimide Acceptor for Additive-Free High-Performance All-Polymer Solar Cells

All-polymer solar cells (all-PSCs) can offer unique advantages for applications in flexible devices, and naphthalene diimide (NDI)-based polymer acceptors are the widely used polymer acceptors. However, their power conversion efficiency (PCE) still lags behind that of state-of-the-art polymer solar cells, due to low light absorption, suboptimal energy levels and the strong aggregation of the NDI-based polymer acceptor. Herein, a rhodanine-based dye molecule was introduced into the NDI-based polymer acceptor by simple random copolymerization and showed an improved light absorption coefficient, an up-shifted lowest unoccupied molecular orbital level and reduced crystallization. Consequently, additive-free all-PSCs demonstrated a high PCE of 8.13 %, which is one of the highest performance characteristics reported for all-PSCs to date. These results indicate that incorporating a dye into the n-type polymer gives insight into the precise design of high-performance polymer acceptors for all-PSCs.

Side-chain engineering of benzodithiophene-thiophene copolymers with conjugated side chains containing the electron-withdrawing ethylrhodanine group

Four benzodithiophene (BDT)-thiophene (T) copolymers with conjugated side chains containing electron-withdrawing ethylrhodanine acceptor units, PHDBDT-T-R, PEHBDT-T-R, PHDBDT-T-TR, and PEHBDT-T-TR, were designed and synthesized for investigating the effect of side chains on the physicochemical properties and photovoltaic performance of the conjugated polymers. All the four copolymers possess an identical conjugated backbone of alternative benzodithiophene-thiophene, but different side chains on BDT and thiophene units, respectively. Polymer solar cells (PSCs) with these polymers as donors and PC70BM as acceptors exhibit an initial power conversion efficiency (PCE) of 0.61% for PHDBDT-T-R, 2.32% for PEHBDT-T-R, 1.46% for PHDBDT-T-TR, and 2.36% for PEHBDT-T-TR. After the treatment with 3 vol% DIO additive and with methanol, the highest PCE was increased up to 1.01%, 4.04%, 3.47%, and 4.25% for PHDBDT-T-R, PEHBDT-T-R, PHDBDT-T-TR, and PEHBDT-T-TR, respectively, with significantly increased Jsc and FF. The effects of methanol treatment on the photovoltaic performance of the PSCs can be ascribed to the increased carrier transport, improved exciton dissociation and optimized phase separation of the active layer. This work indicates that side-chain engineering plays a key role in molecular structures and optoelectronic properties.

Polythiophenes bearing electron-withdrawing groups in the side chain and their application to bulk heterojunction solar cells

Soluble polythiophenes bearing strong electron withdrawing groups, dicyanoethenyl [-CH=C(CN)2] (PTDCN) and cyano-methoxycarbonylethenyl [-CH=C(CO2Me)CN] (PTCNME), in the side chains have been prepared. Optical band gaps calculated from onset absorption were 1.70 eV and 1.73 eV for PTDCN and PTCNME, respectively. Highest occupied molecular orbital energy levels measured with a surface analyzer (AC-2) were -5.53 eV and -5.29 eV for PTDCN and PTCNME, respectively, which were much lower than that of poly(3-hexylthiophene) (-4.81 eV). To investigate photovoltaic properties, bulk heterojunction polymer solar cells based on PTDCN and PTCNME were fabricated with a structure of ITO/PEDOT:PSS/active layer/LiF/Al, where the active layer was a blend film of polymer and [6,6]-phenyl C61 butyric acid hexyl ester (PC61BH). Solar cell parameters were estimated from current density-voltage (J-V) characteristics under the illumination of AM1.5 at 100 mW/cm2. The solar cell based on the blend film of PTCNME:PC 61BH (1:1) showed power conversion efficiency (PCE) of 0.72% together with the open current voltage (Voc) of 0.61 V, the short current density (Jsc) of 3.90 mA/cm2, and the fill factor of 30.3%. The PCE of a solar cell fabricated from PTDCN in a similar way was 0.56%. Copyright

Side chain mediated electronic contact between a tetrahydro-4H-thiopyran-4- ylidene-appended polythiophene and CdTe quantum dots

The properties of a mixed CdTe quantum dot/tetrahydro-4H-thiopyran-4- ylidene-functionalized polythiophene system are reported. This system was prepared by exposing trioctylphosphine (TOP)-capped CdTe quantum dots to the polythiophene in solution. Strong fluorescence emission quenching and shortening of the fluorescence emission lifetimes of both the polythiophene and the quantum dots occur when they are mixed, indicating the occurrence of photoinduced charge separation. Photoinduced absorption spectroscopy reveals a considerable decrease in the population of the polythiophene triplet excited state in the mixed system, These results demonstrate that between the quantum dots and the polythiophene there is both physical and electronic contact, which is mediated by the tetrahydro-4H-thiopyran-4-ylidene side chains.

Synthesis and characterization of reversible chemosensory polymers: Modulation of sensitivity through the attachment of novel imidazole pendants

Three novel electron donor-acceptor conjugated polymers (P1-P3) bearing various imidazole pendants have been synthesized. Their excellent photophysical and electrochemical properties make them suitable transduction materials for chemosensing applications. Indeed, polymers P1-P3 have been found to show remarkable sensing capabilities towards H+ and Fe2+ in semi-aqueous solutions. Upon titration with H+, polymers P1 and P2 showed hypsochromic shifts of their absorptions and photoluminescence (PL) maxima with enhanced fluorescence intensities. However, P3 showed diminished absorption and fluorescence intensities under similar conditions due to static quenching. The anomalous behavior of P3 compared with P1 and P2 has been clarified in terms of electronic distributions through computational analysis. Furthermore, P3 (KSV=1.03×107) showed a superior sensing ability towards Fe2+ compared with P1 (KSV=2. 01×106) and P2 (KSV=4.12×106) due to its improved molecular wire effect. Correspondingly, the fluorescence lifetime of P3 was greatly decreased (almost 11-fold) compared to those of polymers P1 (4.6-fold) and P2 (6.2-fold) in the presence of Fe2+. By means of a fluorescence on-off-on approach, chemosensing reversibilities in protonation-deprotonation and metallation-demetallation have been achieved by employing triethylamine (TEA) and the disodium salt of ethylenediaminetetraacetic acid (Na2-EDTA)/phenanthroline, respectively, as suitable counter ligands. 1H NMR titrations have revealed the unique behavior of P3 compared with P1 and P2. To the best of our knowledge, there have been no previous reports of Fe2+ sensors based on single imidazole receptors conjugated to a main-chain polymer showing such a diverse sensitivity pattern depending on their attached substituents.

Isomerically pure syn-anthradithiophenes: Synthesis, properties, and FET performance

The synthesis of isomerically pure syn-anthradithiophene derivatives (syn-ADTs) is described. X-ray crystallography is used to compare the solid-state arrangement of syn-ADT derivatives 2a,b to the analogous mixture of syn- and anti-ADTs. Single-crystal O

A study on regulating the conjugate position of NLO chromophores for reducing the dipole moment and enhancing the electro-optic activities of organic materials

In order to improve the first-order hyperpolarizability (β) of the chromophore and transform it into a high macroscopic electro-optic activity, a series of novel second-order nonlinear optical chromophores with different push-pull electron groups introduced on the thiophene π-conjugate bridge for tuning the shape and dipole moment (μ) of chromophores were designed and synthesized. These chromophores are based on the same thiophene π-conjugated bridge, where the donor (N,N-diethylaniline) and acceptor (2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile or malononitrile) are linked to positions 2 and 3 of thiophene, respectively, affording a boomerang-like shape instead of a rod-like shape. Besides, an electron-poor group, Br (bromine atom), or an electron-rich group, DEA (N,N-diethylaniline), as an auxiliary acceptor or donor are linked to position 5 of thiophene. In addition, all chromophores showed good thermal stability as per the results from the DSC and TGA analysis. Through UV-vis analysis and DFT calculation, it has been concluded that chromophores with additional electron-rich groups as auxiliary donors display better intermolecular charge-transfer (ICT) absorption and lower HOMO-LUMO energy gaps (ΔE). Furthermore, the boomerang-like chromophore with the same push-pull structure shows a smaller dipole moment (μ) and β value than the traditional FTC. The poling results of guest-host EO polymers FTC/APC, FTC-H/APC, FTC-Br/APC and FTC-DEA/APC with the same number density afford r33 values of 17 pm V-1, 11 pm V-1, 10 pm V-1 and 25 pm V-1, respectively. Although the β value of FTC-DEA is smaller than that of FTC, the r33 value of FTC-DEA (25 pm V-1) is 47% greater than that of FTC (17 pm V-1) under the same number density. Hence, the above-mentioned results indicated that regulating the conjugate position of chromophores can efficiently decrease the dipole moment of the chromophores, weakening the dipole-dipole interactions and thereby enhancing the macroscopic electro-optical activity of poled polymers. These results indicate the potential application of these novel chromophores in electro-optical devices.

Preparation and properties of a novel polythiophene, poly[(3- hexyliminomethyl)thiophene] with a high regioregularity

Poly[(3-hexyliminomethyl)thiophene]s (P3HITs) were synthesized from the polymerizations of 2,5-dibromo-(hexyliminomethyl)thiophene and 5-bromo-2-iodo-3-(hexyliminomethyl)thiophene by Grignard metathesis method. The corresponding P3HITs with low regioregularity (70%) and high regioregularity (95%) were obtained, respectively. UV-vis and photoluminescence spectra of P3HIT were dependent on the regioregularity and solvent polarity. By hydrolysis of the imino groups in the side chains under acidic conditions, P3HIT was successfully converted into the polythiophene (P3TCHO) having aldehyde groups. This transformation was also performed facilely by exposing the P3HIT film to HCl gas to give the polythiophene having aldehyde moiety. The reverse way from aldehyde to imine was also successfully demonstrated by treating the film with triethylamine vapor.