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Usage

Uses

Used in Organic Semiconductor Synthesis:
2,6-Dibromo-4H-cyclopenta-[1,2-b:5,4-b']dithiophen-4-one is utilized as a key component in the synthesis of organic semiconductors due to its distinctive molecular structure that facilitates the creation of materials with enhanced electronic properties.
Used in Optoelectronic Devices:
In the optoelectronics industry, 2,6-Dibromo-4H-cyclopenta-[1,2-b:5,4-b']dithiophen-4-one is employed as a material in the development of optoelectronic devices. Its incorporation into these devices is attributed to its ability to improve the performance of such technologies by leveraging its electronic and photonic characteristics.
Used in Organic Field-Effect Transistors (OFETs):
2,6-Dibromo-4H-cyclopenta-[1,2-b:5,4-b']dithiophen-4-one is also used as a constituent in organic field-effect transistors. Its role in OFETs is crucial for enhancing the transistors' efficiency and performance, capitalizing on the compound's electronic properties to achieve better device operation.
Overall, 2,6-Dibromo-4H-cyclopenta-[1,2-b:5,4-b']dithiophen-4-one is a versatile compound with applications across various industries that require advanced materials for electronic and photonic uses. Its unique attributes make it a valuable asset in the ongoing development of innovative technologies in these fields.

Upstream product

• 19690-69-8 3-bromo-[2,2’]bithiophenyl 
• 125143-53-5 3,3',5,5'-tetrabromo-2,2'-bithiophene 
• 474416-61-0 bis(2-iodo-3-thienyl)methanone 
• 474416-59-6 bis(2-iodothiophen-3-yl)methanol 
• 498-62-4 3-thiophene carboxaldehyde 
• 492-97-7 2,2'-Bithiophene 
• 207742-50-5 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 51751-44-1 3,3'dibromo-2,2'-bithiophene 
• 25796-77-4 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one 
• 1187970-48-4 2,6-bis(trimethylsilyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one 

Relevant academic research and scientific papers

Novel conjugated copolymers with dithienyl and cyclopentadithienyl substituted dicyanoethene acceptor blocks

Novel bifunctional acceptor monomer, 2-[bis(5-bromothiophen-2-yl)methylidene]malononitrile, is obtained in three steps in a total yield of 79%. The Stille cross-coupling between this monomer and 2,6-ditin derivative of 4,4-didecyl-4H-silolo[3,2-b: 4,5-b′]dithiophene afforded donor–acceptor polymer whose properties were compared to the analogue containing a planar cyclopenta[2,1-b: 3,4-b′]dithiophene acceptor block. The copolymers have low narrow optical band gaps and effectively absorb visible light, however the former possesses improved solubility and thermal stability as compared to the latter.

Rethinking Uncaging: A New Antiaromatic Photocage Driven by a Gain of Resonance Energy

Photoactivatable compounds for example photoswitches or photolabile protecting groups (PPGs, photocages) for spatiotemporal light control, play a crucial role in different areas of research. For each application, parameters such as the absorption spectrum, solubility in the respective media and/or photochemical quantum yields for several competing processes need to be optimized. The design of new photochemical tools therefore remains an important task. In this study, we exploited the concept of excited-state-aromaticity, first described by N. Colin Baird in 1971, to investigate a new class of photocages, based on cyclic, ground-state-antiaromatic systems. Several thio- and nitrogen-functionalized compounds were synthesized, photochemically characterized and further optimized, supported by quantum chemical calculations. After choosing the optimal scaffold, which shows an excellent uncaging quantum yield of 28 %, we achieved a bathochromic shift of over 100 nm, resulting in a robust, well accessible, visible light absorbing, compact new photocage with a clean photoreaction and a high quantum product (??Φ) of 893 M?1 cm?1 at 405 nm.

A star-shaped cyclopentadithiophene-based dopant-free hole-transport material for high-performance perovskite solar cells

A new cyclopentadithiophene (CPDT)-based organic small molecule serves as an efficient dopant-free hole transport material (HTM) for perovskite solar cells (PSCs). Upon incorporation of two carbazole groups, the resulting CPDT-based HTM (C-CPDT) shows an impressive power conversion efficiency (PCE) of 19.68% with better stability compared with those of spiro-OMeTAD.

Organic light-emitting material with thermally induced delayed fluorescence performance as well as preparation method and application thereof

The invention discloses an organic light-emitting material with thermally induced delayed fluorescence performance as well as a preparation method and application of the organic light-emitting material, belonging to the technical field of organic light-emitting materials. The organic light-emitting material takes cyclofluorenone dithiophene as a skeleton, and a bipolar organic small molecular light-emitting material is formed by connecting different donor units and receptor units. The organic light-emitting material with the thermally induced delayed fluorescence performance in the invention is of a D-A type structure (Donor-Acceptor type) containing a cyclofluorenone dithiophene unit, has good hole/electron transport property and high fluorescence quantum yield, and can be widely appliedto the fields of organic light-emitting devices, counterfeiting prevention, chemical and biological detection, biological imaging and the like; and a cyclofluorenone dithiophene intermediate preparedin the invention has good solubility in an organic phase, can be used for evaporation devices, and is also suitable for spin-coating devices.

A two-thieno cyclopentanone compound and its preparation method and application (by machine translation)

The present invention discloses a two-thieno cyclopentanone compound and its preparation method and application, which belongs to the technical field of solar cell. Said two thiophene and cyclopentanone compound, the structure of the formula I as shown: Wherein L1 , L2 Respectively and independently represent a hydrogen atom or R, and L1 , L2 At least one is a R. The invention also discloses the above-mentioned two thiophene and cyclopentanone compound of preparation method and application. The compounds of this invention introduced two fragrant amines group is branched, can make the molecule has space three-dimensional structure, to avoid material crystallization; introduced two thiophene and cyclopentanone can greatly improve the thermal stability of the material. (by machine translation)

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.

The effect of heteroatom conformation on optoelectronic properties of cyclopentadithiophene derivatives

Cyclopentadithiophene (CPDT) derivatives with different heteroatom conformations have been synthesized. The optical, electrochemical and charge transport properties of these molecules are reported. The CPDT-anti-ketone not only exhibits the lowest optical and electronic bandgaps, but also exhibits reasonable hole mobility, 3 × 10-3 cm2 (V s) -1. Changing the carbonyl conformation to the syn position or incorporating the imine functionality results in a blue-shift in the lower energy band of the absorption spectrum indicative of the increased bandgaps. the Partner Organisations 2014.

Bridgehead imine substituted cyclopentadithiophene derivatives: An effective strategy for band gap control in donor-acceptor polymers

Bridgehead imine substituted cyclopentadithiophene structural units offer the opportunity to modify the electronic properties, in particular, the HOMO-LUMO energy levels of donor-acceptor polymers with unprecedented precision. Utilizing a common synthetic pathway, copolymers with high average molecular weights, a variety of functionality, and properties suitable for solar cell incorporation can be generated. The fabrication of organic photovoltaic devices with these new materials is demonstrated.

Synthesis and photovoltaic applications of a 4,4′- spirobi[cyclopenta[2,1-b;3,4-b′]dithiophene]-bridged donor/acceptor dye

A new donor/acceptor (D-A) spiro dye (SCPDT1) featuring two bithiophene units, connected through an sp3-hybridized carbon atom, was prepared by a multistep synthetic sequence involving the convenient assembly of the spiro system under mild catalytic conditions. The photocurrent spectrum of dye-sensitized solar cells incorporating SCPDT1 covers the spectral region ranging from 350 to 700 nm and reaches a wide maximum of ～80% in the 420-560 nm range. Power conversion efficiencies of up to 6.02% were obtained.

Substituted oligo- or polythiophenes

A process for the preparation of a substituted 2,2′-dithiophene is described, which process comprises the steps (a), (c) and optional steps (b) and (d): a reaction of a compound of the formula: with a suitable lithium organic compound, preferably Li-alkyl or Li-alkylamide; b) optional exchange of lithium against another metal selected from Mg1 Zn and Cu; c) reaction of the metallated intermediate obtained in step (a) or (b) with a suitable electrophil, which is CO2 or an aldehyde (addition reaction), or a compound Y′—R17 or Y′—R18-Z (substitution reaction), where R17 and R18 are as defined in claim 1; and optionally d) modification of the product obtained in step (c), e.g. by introducing one or more conjugating moieties Y ring closure between suitable monovalent residues R17, exchange or extension of functional groups or substituents such as addition to carbonyl or substitution of carbonyl in R17 or R18. The products, including or corresponding polymers, are excellent conducting materials