40032-88-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(E)-1,2-bis(3-bromothiophen-2-yl)ethene is used as a building block for the synthesis of pharmaceuticals, leveraging its unique molecular structure to create novel drug candidates with potential therapeutic applications.
Used in Agrochemical Development:
In the agrochemical industry, (E)-1,2-bis(3-bromothiophen-2-yl)ethene is utilized as a key component in the development of new pesticides and other agricultural chemicals, contributing to enhanced crop protection and yield.
Used in Electronic Materials:
(E)-1,2-bis(3-bromothiophen-2-yl)ethene is also employed in the creation of electronic materials, where its properties can be harnessed to improve the performance of devices such as sensors, transistors, and other components in the electronics industry.
Safety Note:
It is crucial to handle (E)-1,2-bis(3-bromothiophen-2-yl)ethene with care, as bromine-containing compounds can be toxic and corrosive, necessitating proper safety measures during its use and disposal.

Upstream product

• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 

Relevant academic research and scientific papers

Angular-shaped 4,9-dialkylnaphthodithiophene-based donor-acceptor copolymers for efficient polymer solar cells and high-mobility field-effect transistors

Although the tetracyclic angular-shaped naphthodithiophenes (aNDTs) derivatives are an emergent building block for constructing promising semiconductor conjugated polymers, the absence of aliphatic side chains as solubilizing groups on the aNDTs greatly restricted their further application toward polymer synthesis. To create a new class of aNDT-based polymers for widespread applications in solution-processable OFETs and PSCs, side-chain engineering of the aNDT-based structures plays a pivotal role in improving solubility and optimizing electronic/steric properties associated with the resultant solar cell characteristics. In this research, we developed an efficient and straightforward methodology to construct the angular naphthodithophene core with regiospecific introduction of two aliphatic chains at its 4,9-positions via a base-induced double 6π-cyclization. For the first time, the corresponding 2,7-distannylated-4,9-dialkylated aNDT monomers were polymerized with FBT and DPP acceptors to make two new PaNDTDTFBT and PaNDTDPP donor-acceptor copolymers. The photovoltaic devices based on the PaNDTDTFBT:PC71BM blend not only showed a promising PCE of 6.52% with conventional configuration but also achieved a higher PCE of 6.86% with inverted configuration. Moreover, PaNDTDPP with strong intermolecular interaction achieved a high FET hole mobility of 0.202 cm2 V-1 s-1.

Thiophene-Vinylene-Thiophene-Based Donor-Acceptor Copolymers with Acetylene-Inserted Branched Alkyl Side Chains to Achieve High Field-Effect Mobilities

2-Alkyl(1)alkyl(2)-type aliphatic side chains with a branching point position at the C2-position (such as 2-ethylhexyl or 2-octayldodecyl) have been widely implanted into numerous donor-acceptor conjugated copolymers for solution processable transistors or organic solar cells. However, the tertiary branching site located at the second carbon inevitably imposes steric hindrance that twists the main-chain coplanarity and attenuates interchain interactions. In this research, we developed a new two-dimensonal thiophene-vinylene-thiophene (TVT) derivative where a carbon-carbon triple bond is inserted between the thiophene unit and the 2-octyldodecyl group. This acetylene-incorporated TVT (aTVT) was copolymerized with 5,10-di(thiophen-2-yl)naphtho[1,2-c:5,6-c′]bis([1,2,5]thiadiazole) (DTNT) and 5,6-difluoro-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (DTFBT) to form the polymers PaTVT-NT and PaTVT-FBT, respectively. PTVT-FBT, without the triple bond, was also prepared for comparison. The insertion of a linear triple bond moves the tertiary carbon away from the main chain to reduce the steric hindrance, thereby improving the main-chain coplanarity and facilitating the interchain interactions. The acetylene-incorporated copolymers show better thermal stability, red-shifted absorption spectra, stronger intermolecular aggregation, lower-lying electron affinity, and much higher solid-state crystallinity. Due to the linear and coplanar polymeric backbone supported by theoretical calculation, PaTVT-NT exhibits high crystallinity and adopts strong stacking with an edge-on orientation in the thin film evidenced by 2D-GIXRD, leading to a high p-type OFET mobility up to 1.27 cm2 V-1 s-1 with an on-off ratio of 9.22 × 105. This value represents the highest value among the NT-based polymers. PaTVT-FBT also achieved a high mobility of 0.78 cm2 V-1 s-1, which greatly outperforms the corresponding nonacetylene PTVT-FBT counterpart. Most importantly, the preparation of 2-alkyl(1)alkyl(2)-acetylenyl side chain is synthetically feasible, which can be easily applied to create new conjugated polymers for high-performance solution-processable optoelectronics.

Modulation of Majority Charge Carrier from Hole to Electron by Incorporation of Cyano Groups in Diketopyrrolopyrrole-Based Polymers

A thienylene-vinylene-thienylene (TVT) derivative with cyano groups in the 3- and 3′-positions was synthesized as a building block of semiconducting polymers for high mobility organic field effect transistors (OFETs). (E)-1,2-Di-(3-cyanothiophen-2-yl)ethene (2CNTVT) was copolymerized with diketopyrrolopyrrole (DPP) units via Stille coupling reaction to give 2DPP-2CNTVT and 7DPP-2CNTVT. The properties of these two polymers were compared with those of the corresponding polymers without cyano groups in TVT (2DPP-TVT and 7DPP-TVT). The effects of CN groups and branched alkyl position were found to have a significant influence on the optical, electrochemical, morphological, and charge transporting properties of the polymers. The average hole mobilities of OFETs fabricated with 2DPP-TVT and 7DPP-TVT OFETs were 1.63 and 2.2 cm2 V-1 s-1, respectively, and the average electron mobility for both 2DPP-2CNTVT and 7DPP-2CNTVT OFETs was 1.2 cm2 V-1 s-1.

Angular-Shaped 4,9-Dialkyl α- And β-Naphthodithiophene-Based Donor-Acceptor Copolymers: Investigation of Isomeric Structural Effects on Molecular Properties and Performance of Field-Effect Transistors and Photovoltaics

Two angular-shaped 4,9-didodecyl α-aNDT and 4,9-didodecyl β-aNDT isomeric structures have been regiospecifically designed and synthesized. The distannylated α-aNDT and β-aNDT monomers are copolymerized with the Br-DTNT monomer by the Stille coupling to furnish two isomeric copolymers, PαNDTDTNT and PβNDTDTNT, respectively. The geometric shape and coplanarity of the isomeric α-aNDT and β-aNDT segments in the polymers play a decisive role in determining their macroscopic device performance. Theoretical calculations show that PαNDTDTNT possesses more linear polymeric backbone and higher coplanarity than PβNDTDTNT. The less curved conjugated main chain facilitates stronger intermolecular π-π interactions, resulting in more redshifted absorption spectra of PαNDTDTNT in both solution and thin film compared to the PβNDTDTNT counterpart. 2D wide-angle X-ray diffraction analysis reveals that PαNDTDTNT has more ordered π-stacking and lamellar stacking than PβNDTDTNT as a result of the lesser curvature of the PαNDTDTNT backbone. Consistently, PαNDTDTNT exhibits a greater field effect transistor hole mobility of 0.214 cm2 V-1 s-1 than PβNDTDTNT with a mobility of 0.038 cm2 V-1 s-1. More significantly, the solar cell device incorporating the PαNDTDTNT:PC71BM blend delivers a superior power conversion efficiency (PCE) of 8.01% that outperforms the PβNDTDTNT:PC71BM-based device with a moderate PCE of 3.6%. Two new 4,9-dialkyl α- and β-naphthodithiophene-based D-A copolymers, PαNDTDTNT and PβNDTDTNT, are presented. With the better ordered structures in the solid state, PαNDTDTNT exhibits a greater field-effect transistor hole mobility of 0.214 cm2 V-1 s-1 and a superior solar cell efficiency of 8.01% than PβNDTDTNT with a mobility of 0.038 cm2 V-1 s-1 and a PCE of 3.6%.

Synthesis and molecular properties of four isomeric dialkylated angular-shaped naphthodithiophenes

A new strategy to synthesize 4,9- and 5,10-dialkylated α-aNDTs as well as 4,9- and 5,10-dialkylated β-aNDTs is described. Four isomeric precursors with different dithienyl-ene-diyne arrangements undergo base-induced double 6π-cyclization to construct the central naphthalene cores, leading to the formation of the regiospecific products. These 2,7-distannylated dialkylated aNDT-based monomers can be used for Stille cross-coupling to produce promising conjugated materials for various optoelectronic applications.

Organic semiconducting compounds, manufacturing method thereof, and organic electronics devices containing the same

The present invention relates to an organic semiconductor compound of an organic thin film transistor comprising a thiophene vinylene monomer into which a cyano substituent is introduced at the position 3; a method for producing the same; and an organic electronic device containing the same. The organic semiconductor compound of the present invention has low LUMO energy level, and high thermal stability and solubility, and exhibits excellent n-type electron transfer characteristics in an organic electronic device including the same, particularly an organic thin film transistor device.COPYRIGHT KIPO 2018

Unexpected rearrangement during the gas-phase dehalogenation approach to benzodithiophenes

A range of halogenated methylthiophenes undergo dehalogenative condensation upon FVP over magnesium or calcium to give products including benzodithiophenes; in some cases this involves a novel rearrangement by equilibration of alkenylthienyl radicals via thiophene-fused cyclopropylmethyl intermediates. This journal is

Thiophene-fused borepins as directly functionalizable boron-containing π-electron systems

Synthetic protocols were developed for the gram-scale preparation of two isomeric dithienoborepins (DTBs), boron-containing polycyclic aromatics featuring the fusion of borepin and thiophene rings. DTBs exhibit reversible cathodic electrochemistry and boron-centered Lewis acidity in addition to enhanced electronic delocalization relative to benzo-fused analogues. Borons precise position within the conjugation pathway of DTBs significantly affected electronic structure, most clearly demonstrated by the variation in spectroscopic responses of each isomer to fluoride ion binding. In addition to excellent stability in the presence of air and moisture, DTBs could also be subjected to electrophilic aromatic substitution and metalation chemistry, the latter enabling the direct, regiospecific functionalization of the unsubstituted thiophene rings. Subsequent tuning of molecular properties was achieved through installation of donor and acceptor π-substituents, leading to compounds featuring multistep electrochemical reductions and polarizable electronic structures. As rare examples of directly functionalizable, π-conjugated, boron-containing polycyclic aromatics, DTBs are promising building blocks for the next generation of organoboron π-electron materials whose development will demand broad scope for molecular diversification in addition to chemical robustness.