365547-21-3

Usage

Uses

Used in Organic Electronics:
2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene is used as a key building block for semiconducting polymers in the organic electronics industry. Its planar structure improves the hole mobility of devices, such as polymer solar cells and organic field-effect transistors, leading to enhanced device performance.
Used in Polymer Solar Cells:
In the solar cell industry, 2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene is used as a component in the active layer of polymer solar cells. Its incorporation into the polymer matrix helps to improve the morphology of the thin film, leading to better charge transport and overall device efficiency.
Used in Organic Field-Effect Transistors (OFETs):
2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene is used as a semiconductor material in the fabrication of organic field-effect transistors. The planar structure of the compound contributes to the improved charge carrier mobility, which is crucial for the performance of OFETs.
Used in Suzuki Reaction:
In the field of organic synthesis, 2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene is used as a reactant in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds. This reaction allows for the synthesis of a variety of complex organic molecules, including those with potential applications in materials science and pharmaceuticals.

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 389-58-2 4H-cyclopenta[2,1-b;3,4-b']dithiophene 
• 25796-77-4 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one 
• 31936-92-2 1,1-di(thien-3-yl)-methanol 
• 474416-59-6 bis(2-iodothiophen-3-yl)methanol 
• 474416-61-0 bis(2-iodo-3-thienyl)methanone 
• 78196-93-7 (4H-cyclopenta<2,1-b:3,4-b'>dithiophene)-4-carboxylic acid 
• 365547-20-2 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 
• 18908-66-2 3-bromomethylheptane 

Downstream Products

• 920515-35-1 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4-di(2-ethylhexyl)-4H-cyclopenta-[2,1-b:3,4-b']dithiophene 
• 920504-00-3 4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 

Relevant academic research and scientific papers

Synthesis and characterization of donor-bridge-acceptor alternating copolymers containing perylene diimide units and their application to photovoltaic cells

We have used Suzuki coupling to prepare a series of alternating copolymers featuring coplanar cyclopentadithiophene and hole-transporting carbazole units, We observed quenching in the photoluminescence spectra of our polymers after incorporating pendent electron-deficient perylene diimlde (PDI) moieties on the side chains, indicating more efficient photoinduced electron transfer, Electrochemical measurements revealed that the PDI-containing copolymers displayed reasonable and sufficient offsets of the energy levels of their lowest unoccupied molecular orbitais for efficient charge dissociation, The performance of bulk heterojunction photovoltaic cells incorporating the copolymer/[6, 6]-phenyl-C61-butyric acid methyl ester blends (1:4, w/w) was optimized when the active layer had a thickness of 70 nm, The photocurrents of the devices were enhanced as a result of the presence of the PDI moieties, thereby leading to improved power conversion efficiencies.

Rational design of pyrrolopyrrole-aza-BODIPY-based acceptor-donor-acceptor triads for organic photovoltaics application

Acceptor-donor-acceptor triads consisting of diketopyrrolopyrrole (DPP) or pyrrolopyrrole aza-BODIPY (PPAB) or both as acceptors and cyclopentadithiophene as a donor were rationally designed for near infrared (NIR) photovoltaics application. Among them, the PPAB-based triad exhibited the highest power conversion efficiency of 3.88% owing to the panchromatic absorption in the UV/vis/NIR regions.

Planar quinone structure-containing small molecule organic semiconductor material and preparation and application thereof

The invention relates to a planar quinone structure-containing small molecule organic semiconductor material and preparation and application thereof. The general structural formula of the material isshown in a formula I. The prepared planar quinone structure-based small molecule material has good solubility, can be dissolved in common organic solvents, and organic optoelectronic devices can be prepared through processing of a solution of the small molecule organic semiconductor material; and the small molecule organic semiconductor material has good responses to solar spectra, and thus, can be used as an active layer material of organic solar cells, the migration ability of carriers can be improved due to good planarity of the small molecule organic semiconductor material, and therefore the small molecule organic semiconductor material can also be applied to preparation of active layer materials of organic field-effect transistors.

POLYMER COMPOUND

The invention relates to a polymer compound. A photoelectric conversion device that contains the polymer compound having a structural unit represented by formula (1) has high photoelectric conversion efficiency. (wherein, X1 and X2 are the same or different and represent a nitrogen atom or -CH-. Y1 represents a sulfur atom, an oxygen atom, a selenium atom, -N(R1)- or -CR2-CR3-. R1, R2 and R3 are the same or different and represent a hydrogen atom or a substituent. W1 represents a cyano group, a monovalent organic group having a fluorine atom or a halogen atom. W2 represents a cyano group, a monovalent organic group having a fluorine atom, a halogen atom or a hydrogen atom.

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.

Highly efficient and facile alkylation of 4H-cyclopenta-[2,1-b:3,4- b′]dithiophene in water

A new and highly convenient method to perform alkylation of 4H-cyclopenta-[2,1-b:3,4-b′]dithiophene (CPDT) in aqueous conditions is reported. This method was also extended to successfully perform alkylation of 2,6-dibromo-4H-cyclopenta-[2,1-b:3,4-b′]dithiophene for the first time. This facile method has several advantages such as the exclusive use of water instead of high boiling toxic solvents, simple separation of the defect free dialkylated CPDT product and the use of mild reaction conditions. Despite using mild reagents and reaction conditions, to our delight, very high yields of up to 98% pure dialkylated CPDT products are obtained much more readily by this method in less time than literature procedures. The isolated products were identified by HRMS and solution NMR measurements to be solely the desired dialkylated product with the alkyl halides used here. the Partner Organisations 2014.

Highly efficient and facile alkylation of 4H-cyclopenta-[2,1-b:3,4-b′]dithiophene in water

A new and highly convenient method to perform alkylation of 4H-cyclopenta-[2,1-b:3,4-b′]dithiophene (CPDT) in aqueous conditions is reported. This method was also extended to successfully perform alkylation of 2,6-dibromo-4H-cyclopenta-[2,1-b:3,4-b′]dithiophene for the first time. This facile method has several advantages such as the exclusive use of water instead of high boiling toxic solvents, simple separation of the defect free dialkylated CPDT product and the use of mild reaction conditions. Despite using mild reagents and reaction conditions, to our delight, very high yields of up to 98% pure dialkylated CPDT products are obtained much more readily by this method in less time than literature procedures. The isolated products were identified by HRMS and solution NMR measurements to be solely the desired dialkylated product with the alkyl halides used here. This journal is

Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.

Influence of different copolymer sequences in low band gap polymers on their performance in organic solar cells

The chemical design of a polymer can be tailored by a random or a block sequence of the comonomers in order to influence the properties of the final material. In this work, two sequences, PCPDTBT and F8BT (F8), were polymerized to form a block or a random copolymer. Differences between the various polymers were examined by exploring the surface topography and charge carrier mobility. A distinct surface texture and a higher charge carrier mobility was found for the block copolymer with respect to the other materials. Solar cells were prepared with polymer:PC71BM blend active layers and the best performance of up to 2% was found for the block copolymer, which was a direct result of the fill factor. Overall, the sequences of different copolymers for solar cell applications were varied and a positive impact on efficiency was found when the block copolymer structure was utilized.

A versatile approach to organic photovoltaics evaluation using white light pulse and microwave conductivity

State-of-the-art low band gap conjugated polymers have been investigated for application in organic photovoltaic cells (OPVs) to achieve efficient conversion of the wide spectrum of sunlight into electricity. A remarkable improvement in power conversion efficiency (PCE) has been achieved through the use of innovative materials and device structures. However, a reliable technique for the rapid screening of the materials and processes is a prerequisite toward faster development in this area. Here we report the realization of such a versatile evaluation technique for bulk heterojunction OPVs by the combination of time-resolved microwave conductivity (TRMC) and submicrosecond white light pulse from a Xe-flash lamp. Xe-flash TRMC allows examination of the OPV active layer without requiring fabrication of the actual device. The transient photoconductivity maxima, involving information on generation efficiency, mobility, and lifetime of charge carriers in four well-known low band gap polymers blended with phenyl-C61-butyric acid methyl ester (PCBM), were confirmed to universally correlate with the PCE divided by the open circuit voltage (PCE/Voc), offering a facile way to predict photovoltaic performance without device fabrication.