153312-87-9

Basic information

• Product Name: K0493
• Synonyms: 4,4-Dioctyl-cyclopenta[2,1-b:3,4-b']dithiophene
• CAS NO: 153312-87-9
• Molecular Formula: C₂₅H₃₈S₂
• Molecular Weight: 402.699
• Mol File: 153312-87-9.mol

Chemical Properties

• CAS DataBase Reference: K0493(CAS DataBase Reference)
• NIST Chemistry Reference: K0493(153312-87-9)
• EPA Substance Registry System: K0493(153312-87-9)

Safety Data

• Hazardous Substances Data: 153312-87-9(Hazardous Substances Data)

Usage

Uses

Due to the lack of information on K0493, it is not possible to list its uses or applications in different industries. It is recommended to verify the chemical's unique identifier and gather more data to accurately determine its potential applications.

Upstream product

• 389-58-2 4H-cyclopenta[2,1-b;3,4-b']dithiophene 
• 111-83-1 1-bromo-octane 
• 1253119-61-7 9-([2,2'-bithiophen]-3-yl)heptadecan-9-ol 
• 111-85-3 n-chlorooctane 
• 22913-26-4 methyl thiophene-3-carboxylate 
• 17049-49-9 octylmagnesium bromide 
• 19690-69-8 3-bromo-[2,2’]bithiophenyl 
• 540-08-9 heptadecan-9-one 
• 2243-27-8 nonanonitrile 
• 25796-77-4 4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one 

Relevant articles and documents

Fused Cyclopentadithienothiophene Acceptor Enables Ultrahigh Short-Circuit Current and High Efficiency >11% in As-Cast Organic Solar Cells

A new method to synthesize an electron-rich building block cyclopentadithienothiophene (9H-thieno-[3,2-b]thieno[2″,3″:4′,5′]thieno[2′,3′:3,4]cyclopenta[1,2-d]thiophene, CDTT) via a facile aromatic extension strategy is reported. By combining CDTT with 1,1-dicyanomethylene-3-indanone endgroups, a promising nonfullerene small molecule acceptor (CDTTIC) is prepared. As-cast, single-junction nonfullerene organic solar cells based on PFBDB-T: CDTTIC blends exhibit very high short-circuit currents up to 26.2 mA cm?2 in combination with power conversion efficiencies over 11% without any additional processing treatments. The high photocurrent results from the near-infrared absorption of the CDTTIC acceptor and the well-intermixed blend morphology of polymer donor PFBDB-T and CDTTIC. This work demonstrates a useful fused ring extension strategy and promising solar cell results, indicating the great potential of the CDTT derivatives as electron-rich building blocks for constructing high-performance small molecule acceptors in organic solar cells.

The rational design of a redox-active mixed ion/electron conductor as a multi-functional binder for lithium-ion batteries

A redox-active mixed ion and electron conductor (redox-active MIEC) is presented as a binder for the lithium titanate anodes of lithium-ion batteries. The redox-active MIEC binder (symbolized by PT*-GmCn) was designed to be (1) electrically conductive along its conjugated thiophene backbone (PT = polythiophene), (2) redox-active from its succinimide moiety (* = redox-active) and (3) ionically conductive by adopting glyme (G) branches. It was superior to the practically used PVdF binder in terms of lithium ion diffusivity and electrical conductivity (1.4× and 15?000×, respectively). High capacity was guaranteed, particularly at high rates due to its MIEC nature of PT*-GmCn, while an additional capacity was achieved from its redox activity.

Synthesis and photovoltaic properties of cyclopentadithiophene-based low-bandgap copolymers that contain electron-withdrawing thiazole derivatives

We have synthesized four types of cyclopentadithiophene (CDT)based low-bandgap copolymers, poly[{4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1 -b :3,4-b']dithiophene-2,6-diy1}-alt(2,2'-bithiazole-5,5'-diy1)] (PehCDTBT), poly[(4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6-diyl)-alt(2, 2'-bithiazole-5,5'-diyl)] (PocCDTBT), poly[{4,4-bis(2-ethylhexyl)-4H- cyclopenta[2,1-b:3,4-b)']dithiophene-2,6diyl}-alt-{2,5-di(thiophen-2-y1) thiazolo[5,4-d]thiazole-5,5'-diy1}] (PehCDTTZ), and poly[(4,4-dioctyl-4H- cyclopenta[2,1-b:3,4-b']dithiophene-2,6diyl)-alt-{2,5-di(thiophen-2-y1) thiazolo[5,4-d]thiazole-5,5'-diy1}] (PocCDTTZ), for use in photovoltaic applications. The intramolecular charge-transfer interaction between the electronsufficient CDT unit and electron-deficient bithiazole (BT) or thiazolothiazole (TZ) units in the polymeric backbone induced a low bandgap and broad absorption that covered 300 nm to 700800 nm. The optical bandgap was measured to be around 1.9 eV for PehCDT-BT and PocCDT-BT, and around 1.8 eV for PehCDT-TZ and PocCDT-TZ. Gel permeation chromatography showed that number-average molecular weights ranged from 8000 to 14000 g mol-1. Field-effect mobility measurements showed hole mobility of 10 6-10-4 Cm2V-1 s-1 for the copolymers. The film morphology of the bulk heteroj unction mixtures with [6,6]phenyl-C61-butyric acid methyl ester (PCBM) was also examined by atomic force microscopy before and after heat treatment. When the polymers were blended with PCBM, PehCDT-TZ exhibited the best performance with an open circuit voltage of 0.69 V, short-circuit current of 7.14 mA cm-2, and power conversion efficiency of 2.23% under air mass (AM) 1.5 global (1.5 G) illumination conditions (100 mWcm-2).

A three-step synthetic approach to asymmetrically functionalized 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes

A convenient and efficient three-step route toward both symmetrically and asymmetrically functionalized 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes has been developed. Using this method a broad collection of functionalized bridged bithiophenes can smoothly be accessed. Starting from 3-bromo-2,2′- bithiophene, prepared by Kumada coupling of 2-thienylmagnesium bromide with 2,3-dibromothiophene under Pd(dppf)Cl2 catalysis, lithiation and subsequent reaction with dialkyl ketones afforded (a)symmetrically dialkylated tertiary alcohol derivatives. By means of final Friedel-Crafts dehydration cyclization in sulfuric acid medium, these derivatives were converted to 4,4-dialkyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes. Upon replacement of the dialkyl ketone reagent by ethyl levulinate, an ester-functionalized 4H-cyclopenta[2,1-b:3,4-b′]dithiophene was prepared, representing an attractive precursor for variously functionalized cyclopentadithiophene compounds.

New routes to poly(4,4-dialkylcyclopentadithiophene-2,6-diyls)

Two new polymerisation routes to poly(4,4-dioctylcyclopentadithiophene-2,6-diyl) are reported. The polymer prepared by Kumada type cross-coupling showed significantly reduced molecular weight over that prepared by direct oxidative polymerisation using iron(III) chloride. The higher molecular weight polymer was shown to have extended conjugation by UV-visible spectroscopy.

Near-Infrared Nonfullerene Acceptors Based on 4H-Cyclopenta[1,2-b:5,4-b′]dithiophene for Organic Solar Cells and Organic Field-Effect Transistors

The development of nonfullerene small molecular acceptors (NF-SMAs) has dominated the improvement of efficiencies for organic solar cells and the near-infrared (NIR) absorption is the primary feature of NF-SMAs compared with fullerene derivatives. In this article, a series of acceptor-donor-acceptor-structured NF-SMAs (named CPICs) containing 4H-cyclopenta[1,2-b : 5,4-b′]dithiophene (CPDT) electron donor and F-substituted 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2FIC) as electron acceptor were designed and synthesized. With the increase of CPDT units, the elongated conjugations broadened the absorption range of the acceptors and tuned their energy levels sequentially. Therefore, their charge-transporting polarities switched from electron-only type to bipolar mode in organic field-effect transistors. Moreover, these changes also influenced the voltages, current densities, and eventual PCEs of their corresponding cells. When blending with PBDB-T, a champion efficiency of 10.01% was achieved in CPIC-2 based cells. This work demonstrated the importance of absorptions, suitable energy levels and charge transports in improving the efficiencies of organic solar cells.

A two-thieno cyclopentadiene derivative and its preparation method (by machine translation)

The invention belongs to the technical field of organic photoelectric material, in particular to a two-thieno cyclopentadiene derivative and its preparation method. The invention discloses a two-thieno cyclopentadiene derivatives, the structural formula of Wherein R, R ' is C1 - C20 Alkyl, C1 - C10 C alkyl substituted phenyl or1 - C10 Alkyl substituted thienyl. The 2 - bromo thiophene, 3 - thiophene methyl formate and alkali soluble in organic solvent, under the action of the metal catalyst in the reflux reaction for 24 hours, then with an organic metal reagent reaction, after the strong acid ring can be 78 - 86% yields of two thiophene and a cyclopentadiene derivative. With the present invention novel, simple steps, high yield, the advantages of the product separation and purification. In addition, the invention relates to a two-thieno cyclopentadiene derivative structure comprising multiple parallel fused ring, conjugacy is strong, and can be used as organic photoelectric material field. (by machine translation)

Effects of alkyl chains on intermolecular packing and device performance in small molecule based organic solar cells

Two donor molecules named as DR3TDTC-C6 and DR3TDTC-C8 with n-hexyl and n-octyl alkyl chains on the central building block 7H-cyclopenta-[1,2-b:3,4-b’]-dithiophene (DTC) were designed and synthesized. Both of them exhibited PCEs >4%. The photovoltaic properties of these molecules were superior to their analogous donor molecule DR3TDTC, which possess two 2-ethyl hexyl alkyl chains on the same core unit and only demonstrated a PCE of 0.75% after elaborative post-treatment. The influence of the alkyl chains on the optical, electrochemical properties, packing properties and morphology of these three molecules was systematically investigated. The results demonstrated that the difference between their device performances is mainly affected by their intermolecular packing state. This indicates that length and branch structure of alkyl chains on the central unit should be given careful consideration while designing donor molecules for small molecular organic solar cells.

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