cas 25796-77-4, 4H-Cyclopenta[2,1-b:3,4-b']dithiophen-4-one

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A new, improved and convenient synthesis of 4H-cyclopenta[2,1-b:3,4-b′]-dithiophen-4-one
A new and efficient three-step synthesis of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (CDT) (1) is described. This was achieved by a one-pot, regiospecific synthesis of bis(2-iodo-3-thienyl)methanol (13), its subsequent oxidation to the bls(2-iodo-3-thienyl) ketone (14) which after Ullmann coupling yielded the title compound 1.
Brzezinski, Jacek Z.,Reynolds, John R.
p. 1053 - 1056
(2002)
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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.
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Paragraph 0059-0062

(2021/01/28)

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
The present specification relates to a compound and an organic light emitting device comprising the same. The compound is represented by chemical formula 1. The abovementioned compound can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one embodiment of the present invention can improve the efficiency, the low driving voltage and/or the lifetime characteristics in the organic light emitting device.COPYRIGHT KIPO 2018
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Page/Page column 0139; 0140; 0145; 0146; 0153; 0154

(2018/09/25)

An effective strategy to enhance the dielectric constant of organic semiconductors-CPDTTPD-based low bandgap polymers bearing oligo(ethylene glycol) side chains
Conjugated polymers applied in organic electronics (notably photovoltaics and photodetectors) generally exhibit relatively low dielectric constants (?r 3-4), which leads to significant recombination losses of photogenerated excitons. As a direct consequence, the performance of the resulting devices is inherently restricted. Some efforts have been directed toward increasing ?r of the photoactive organic compounds, but the general knowledge on the impact of specific structural variations on the dielectric constant and the final device output remains rather limited. In this study, this problem is addressed. A series of push-pull type alternating copolymers is synthesized based on 4H-cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT) and 4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (TPD) subunits, with the aim to increase the dielectric constant using oligo(ethylene glycol) side chains. The amount of glycol substituents on the polymer backbone is gradually raised to systematically investigate its influence on the dielectric properties. Impedance measurements reveal a doubling of the dielectric constant (up to ?r 6.3) with respect to the reference polymer. Upon applying these materials in bulk heterojunction polymer solar cells, an efficiency of 4.4% is obtained for the best-performing device, with a particularly higher short-circuit current and improved fill factor compared to the pristine alkyl-substituted polymer. Importantly, a non-halogenated solvent-beneficial toward 'green' processing-can also be applied for the active layer deposition, affording comparable results.
Brebels, Jeroen,Douvogianni, Evgenia,Devisscher, Dries,Thiruvallur Eachambadi, Raghavendran,Manca, Jean,Lutsen, Laurence,Vanderzande, Dirk,Hummelen, Jan C.,Maes, Wouter
p. 500 - 511
(2018/02/06)

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)
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Paragraph 0058; 0059; 0060

(2018/08/03)

Molecular engineering of face-on oriented dopant-free hole transporting material for perovskite solar cells with 19% PCE
Through judicious molecular engineering, novel dopant-free star-shaped D-π-A type hole transporting materials coded KR355, KR321, and KR353 were systematically designed, synthesized and characterized. KR321 has been revealed to form a particular face-on organization on perovskite films favoring vertical charge carrier transport and for the first time, we show that this particular molecular stacking feature resulted in a power conversion efficiency over 19% in combination with mixed-perovskite (FAPbI3)0.85(MAPbBr3)0.15. The obtained 19% efficiency using a pristine hole transporting layer without any chemical additives or doping is the highest, establishing that the molecular engineering of a planar donor core, π-spacer and periphery acceptor leads to high mobility, and the design provides useful insight into the synthesis of next-generation HTMs for perovskite solar cells and optoelectronic applications.
Rakstys, Kasparas,Paek, Sanghyun,Gao, Peng,Gratia, Paul,Marszalek, Tomasz,Grancini, Giulia,Cho, Kyung Taek,Genevicius, Kristijonas,Jankauskas, Vygintas,Pisula, Wojciech,Nazeeruddin, Mohammad Khaja
supporting information
p. 7811 - 7815
(2017/07/13)

Ligand Engineering for the Efficient Dye-Sensitized Solar Cells with Ruthenium Sensitizers and Cobalt Electrolytes
Over the past 20 years, ruthenium(II)-based dyes have played a pivotal role in turning dye-sensitized solar cells (DSCs) into a mature technology for the third generation of photovoltaics. However, the classic I3-/I- redox couple limits the performance and application of this technique. Simply replacing the iodine-based redox couple by new types like cobalt(3+/2+) complexes was not successful because of the poor compatibility between the ruthenium(II) sensitizer and the cobalt redox species. To address this problem and achieve higher power conversion efficiencies (PCEs), we introduce here six new cyclometalated ruthenium(II)-based dyes developed through ligand engineering. We tested DSCs employing these ruthenium(II) complexes and achieved PCEs of up to 9.4% using cobalt(3+/2+)-based electrolytes, which is the record efficiency to date featuring a ruthenium-based dye. In view of the complicated liquid DSC system, the disagreement found between different characterizations enlightens us about the importance of the sensitizer loading on TiO2, which is a subtle but equally important factor in the electronic properties of the sensitizers.
Aghazada, Sadig,Gao, Peng,Yella, Aswani,Marotta, Gabriele,Moehl, Thomas,Teuscher, Jo?l,Moser, Jacques-E.,De Angelis, Filippo,Gr?tzel, Michael,Nazeeruddin, Mohammad Khaja
supporting information
p. 6653 - 6659
(2016/07/19)

C-H/C-H rhodium catalysis -based high-efficiency oxidation coupling reaction of preparing double-hetero aromatic ring and pyronone/cyclopentanone derivatives method
The invention relates to a method for efficiently preparing a di(hetero)arylbenzopyrone/cyclopentanone derivative through a rhodium catalysis-based C-H/C-H oxidation coupling reaction. The method comprises the following steps: 1, carrying out direct cross coupling on the C-H bond at the ortho position of the carboxyl group of a raw material (hetero)aryl carboxylic acid derivative and the C-H bond of a heteroarene derivative under the catalysis of rhodium to obtain an intermediate (orthoheteroaryl(hetero) aryl carboxylic acid derivative); and 2, carrying out an intramolecular acylation or esterification reaction to obtain the (hetero) arylbenzopyrone/cyclopentanone derivative. Compared with traditional methods, the preparation method provided by the invention has the advantages of concise synthesis steps, mild conditions, high synthesis yield, and cheap and easily available raw materials.
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(2017/04/20)

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.
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(2016/10/07)

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.
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(2016/10/08)

Compound
PROBLEM TO BE SOLVED: To provide a method of producing a compound free of an ester borate residue and an organotin residue by allowing two or more species of heterocyclic compounds to react with each other. SOLUTION: The method of producing the compound includes allowing a compound represented by formula (1) (in the formula, Ar1represents a heteroarylene compound and H represents a hydrogen atom) and a compound represented by formula (2) (in the formula, Ar2represents a heteroarylene compound and X represents a chlorine atom, a bromine atom or an iodine atom, provided that two X may be the same or different) to react with each other in the presence of an alkaline compound or a phosphine compound. COPYRIGHT: (C)2013,JPOandINPIT
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(2020/10/21)

Rhodium(III)-catalyzed ortho c-h heteroarylation of (hetero)aromatic carboxylic acids: A rapid and concise access to π-conjugated poly-heterocycles
Abstract RhIII-catalyzed oxidative Ci-H/Ci-H cross-coupling between (hetero)aromatic carboxylic acids and various heteroarenes has been accomplished to construct highly functionalized ortho-carboxy-substituted bi(hetero)aryls. The use of a carboxy group as the directing group obviates tedious steps for installation and removal of extra directing groups, and enables a facile one-step synthesis of ortho-carboxy bi(hetero)aryls. The method provides opportunities for rapid assembly of a library of important fluorene and coumarin-type poly-heterocycles through intramolecular electrophilic substitution or oxidative lactonization. As illustrative examples, the strategy developed herein greatly streamlines accesses to a variety of appealing polyheterocycles such as DTPO (5H-dithieno[3,2-b:2',3'-d]pyran-5-one), CPDTO (cyclopentadithiophen-4-one), and indenothiophenes. Under construction: The highly regioselective title reaction directly furnishes ortho-carboxy bi(hetero)aryls. The method has the potential to lead to the rapid construction of a library of appealing poly-heterocycles, given the complete regiocontrol, readily available substrates, and functional-group tolerance.
Qin, Xurong,Li, Xiaoyu,Huang, Quan,Liu, Hu,Wu, Di,Guo, Qiang,Lan, Jingbo,Wang, Ruilin,You, Jingsong
supporting information
p. 7167 - 7170
(2015/06/08)

A versatile synthesis of long-wavelength-excitable BODIPY dyes from readily modifiable cyclopenta[2,1- B:3,4- B′ ]dithiophenes
Knoevenagel condensation of a simple methylated borondipyrromethene (Bodipy) with 4,4′-dihexyl-4H-cyclopenta-[2,1-b:3,4-b′]dithiophenes functionalized at one end by a triphenylamine residue and at the other by a carbaldehyde fragment leads to novel dye species. These bisvinylic derivatives exhibit pronounced absorption in the visible range extending above 850 nm. Addition of other Bodipy units by coupling to a central iodophenyl entity enables filling of the gaps in absorption of the pivotal starting material. Efficient cascade energy transfer between the Bodipys is facilitated by spectral overlap between the energy donor and the energy acceptor. All photons between 350 nm and 750 nm are channeled to the distyryl centers which emit at 864 nm. Georg Thieme Verlag Stuttgart. New York.
Sutter, Alexandra,Ziessel, Raymond
p. 1466 - 1472
(2014/06/23)

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.
Pozzi, Gianluca,Orlandi, Simonetta,Cavazzini, Marco,Minudri, Daniela,Macor, Lorena,Otero, Luis,Fungo, Fernando
supporting information
p. 4642 - 4645
(2013/10/08)

Synthesis and characterization of bridged bithiophene-based conjugated polymers for photovoltaic applications: Acceptor strength and ternary blends
Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)m -(thiophene acceptor)n, were rationally designed and successfully synthesized by the palladium-catalyzed Stille coupling. The 4H-cyclopenta[2,l-b:3,4-b']dithiophene (CPDT) unit serves as the donor for Pl-P4, while the benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, respectively. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3,2-b:2',3'-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BT > QU presumably due to the quinoid form population in the polymers, the optical band gaps can be well adjusted to be 1.2,1.6, and 1.8 eV for P4, P1, and P2, respectively. It is found that the two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects on the P1 and P5 as well as P2 and P6, respectively, leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based on ITO/PEDOT:PSS/polymer:PC7BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b'] dithiophene)-alt-4,7-(2,l,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows a higher band gap with strong absorption in visible region, while PCPDTBT has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P1/PC71BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/ PC71BM(PCE = 1.4%)orP1/PC71BM(PCE = 2.0%) under the identical conditions. Such an improvement is ascribed to the complementary absorption and compatible structure of P1 and PCPDTBT polymers.
Chen, Chiu-Hsiang,Hsieh, Chao-Hsiang,Dubosc, Martin,Cheng, Yen-Ju,Hsu, Chain-Shu
p. 697 - 708
(2011/10/08)

Expedient synthesis of symmetric aryl ketones and of ambient-temperature molten salts of imidazole
A short procedure for the synthesis of 2,2-di(3-thienyl)-1,3-dioxolan is described. The route developed is convenient (only two synthetic and one chromatographic steps are required) and efficient (66% overall yield from 3-bromothiophene). This compound was transformed into the ketone, cyclopenta[2,1-b:3',4'-b']dithiophen-4-one by a known process. Optimized syntheses of symmetric aryl ketones, 1-alkyl-3-methylimidazolium and 1-alkyl-2-methyl-3-methylimidazolium liquid salts are also reported.
Lucas,El Mehdi,Ho,Belanger,Breau
p. 1253 - 1258
(2007/10/03)

Thermolysis of Thiophenedicarboxylic Acid Anhydrides as a Route to Five-Membered Hetarynes
Flow vacuum thermolysis (FVT) of the anhydrides of thiophene-2,3- (5) and -3,4-dicarboxylic acid (6) and of thianaphthene-2,3-dicarboxylic acid (7) in the presence of thiophene, 1,3-cyclohexadiene, or benzene gave thianthrene (15a), presumably by aromatization of an intermadiate Diels-Alder adduct of the diene traps and the aryne 2,3-didehydrothiophene (8).A similar rationale explains the formation of dibenzothiophene from 7 and thiophene, the four monomethylthianaphthenes 22-25 from 5 and cyclopentadiene, 5,6-dimethylthianaphthene (15f) from 5 and 2,3-dimethylbutadiene, and a mixture of hydroxythianaphthenes (15d) from 5 and furan.The latter reaction also produces a mixture of isomeric cyclopentanothiophenes (19) which probably arise by decarbonylation of 15d.An FVT reaction of 5 with propyne as the trap gave a mixture of allenyl-(28) and propynylthiophenes 29 which probably arise by an ene reaction of the trap and the aryne 8.Decomposition of the anhydrides 5 and 6 in molten anthracene led only to Friedel-Crafts products such as thienylanthracenes 33 and quinones 34 from 5 and 39 and 40 from 6.The diene reactivity of thiophene 13a in the gas phase was demonstrated by the formation of naphthalene from its reaction with benzyne generated from the thermolysis of indanetrione and by the formation of indene from 13a plus cyclopentadiene.Possible, but improbable, interpretations of the FVT results without invoking a five-membered hetaryne intermediate are considered.
Reinecke, Manfred G.,Newsom, James G.,Chen, Lao-Jer
p. 2760 - 2769
(2007/10/02)