- Photocatalytic polymers of intrinsic microporosity for hydrogen production from water
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The most common strategy for introducing porosity into organic polymer photocatalysts has been the synthesis of cross-linked conjugated networks or frameworks. Here, we study the photocatalytic performance of a series of linear conjugated polymers of intrinsic microporosity (PIMs) as photocatalysts for hydrogen production from water in the presence of a hole scavenger. The best performing materials are porous and wettable, which allows for the penetration of water into the material. One of these polymers of intrinsic microporosity, P38, showed the highest sacrificial hydrogen evolution rate of 5226 μmol h?1g?1under visible irradiation (λ> 420 nm), with an external quantum efficiency of 18.1% at 420 nm, placing it among the highest performing polymer photocatalysts reported to date for this reaction.
- Bai, Yang,Wilbraham, Liam,Gao, Hui,Clowes, Rob,Yang, Haofan,Zwijnenburg, Martijn A.,Cooper, Andrew I.,Sprick, Reiner Sebastian
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supporting information
p. 19958 - 19964
(2021/09/20)
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- NEAR-INFRARED ABSORBING DYE, OPTICAL FILTER, AND IMAGING DEVICE
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A near-infrared absorbing dye includes a compound represented by formula (A). Each of R11 to R14 is independently a hydrogen atom, a halogen atom, a hydroxyl group, or an alkyl, aryl or alaryl group. Each of pairs R11 and R12, R12 and R13, and R13 and R14 may combine with one another to form a monocyclic ring or a polycyclic ring in which from 2 to 4 rings are fused. Each of R15 and R16 is independently an alkyl or alaryl group. R15 and R16 may combine with one another to form a cyclohetero ring having from 5 to 10 members together with the nitrogen atom.
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Paragraph 0163-0164; 0180-0181
(2021/03/13)
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- Fluorobenzotriazole-Based Medium-Bandgap Conjugated D–A Copolymers for Applications to Fullerene-Based and Nonfullerene Polymer Solar Cells
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Two new medium-bandgap (MBG) donor–acceptor (D–A) conjugated polymers (PSTF and PDTS) with fluorobenzotriazole as an A unit and spiro[cyclopenta[1,2-b:5,4-b′]dithiophene-4,9′-fluorene] (STF) or dithienosilole (DTS) as the D unit are designed and synthesized as donor materials for polymer solar cell (PSC) applications. PSTF shows a broader absorption spectrum relative to PDTS reflecting an additional high-energy absorption band due to the conjugated thiophene side chains on STF moiety. Compared with PDTS, PSTF exhibits weaker π–π aggregation and lower lying HOMO level. Photovoltaic properties of the PSCs reveal that either PSTF or PDTS using PC61BM as acceptor exhibits better performances than that of ITIC as acceptor, which results from the simultaneously increased Voc, Jsc, and FF of PC61BM-based PSCs. Moreover, when combined with PC61BM and ITIC, the PSTF-based PSCs exhibit an efficiency of 3.66% and 2.42%, respectively, which is 45% and almost 1.5 times higher than that of the PDTS-based PSCs, respectively. This can be ascribed to the obviously improved Voc and FF of PSTF-based PSCs benefitted from the deeper HOMO level and better active layer morphology. Our work demonstrates that using spiro-annulated building block as donor unit to construct MBG D-A copolymers is an alternative and effective approach for achieving efficient donor materials in PSCs.
- Weng, Chao,Wang, Wengong,Liang, Jingtang,Wang, Guo,Tan, Songting,Shen, Ping
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p. 2330 - 2343
(2018/09/27)
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- Polythiophenes with Thiophene Side Chain Extensions: Convergent Syntheses and Investigation of Mesoscopic Order
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A versatile convergent synthesis route to side chain π-extended, highly regioregular polythiophenes is presented. The implementation of β-conjugated alkyl thiophene branches in linear polythiophenes is used as synthetical tool for energy level engineering, with branched alkyl chains being introduced for solubility reasons. While the length of the branched alkyl side chains does not influence the functional properties, the aggregation behavior in solution does vary from highly aggregated to fully dissolved at room temperature. Temperature-dependent UV-vis spectroscopy highlights the differences in the aggregation behavior in solution and thin films. The aggregation behavior in solid state is further studied using DSC, temperature-dependent Raman spectroscopy and temperature-dependent XRD. Finally, controlled crystallization conditions via solvent vapor annealing are applied to allow the formation of spherulite-like structures which reveal a face-on orientation of the polymer backbone with respect to the substrate.
- Scheuble,Gross,Trefz,Brinkmann,López Navarrete,Ruiz Delgado,Ludwigs
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p. 7049 - 7059
(2015/10/28)
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- Condensed compound and organic light emitting diode comprising the same
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Provided are a condensed cyclic compound represented by chemical formula 1 and an organic electroluminescent device comprising the same. In the chemical formula 1, X, and R1 to R10 refer to the detailed description of the present invention. An organic light emitting device having an organic layer comprising the condensed cyclic compound has properties of low driving voltage, high light emitting efficiency and long lifespan.COPYRIGHT KIPO 2016
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Paragraph 0312; 0313; 0316
(2016/12/01)
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- A bridged low band gap A-D-A quaterthiophene as efficient donor for organic solar cells
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α,ω-Bis(dicyanovinyl)quaterthiophene 1 with a median 4,4-diethyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene has been synthesized. UV-Vis absorption data show that the covalent bridging of the inner 2,2′-bithiophene leads to a significant reduction of the HOMO-LUMO gap essentially due to an increase of the HOMO level as confirmed by electrochemical and theoretical results. X-ray diffraction analysis of a single crystal of 1 shows that except for the out-of-plane ethyl groups, the conjugated system displays a quasi-planar geometry while the molecular packing exhibits strong π-stacking interactions and multiple short intermolecular contacts. Quaterthiophene 1 has been used as active donor material in organic solar cells of various architectures including bi-layer planar hetero-junctions and hybrid co-evaporated bulk hetero-junctions with C60 as electron acceptor material. A maximum conversion efficiency of 4.30% is obtained with a hybrid co-evaporated device. These results are discussed in terms of structure-properties relationships with reference to the open-chain parent α,ω-bis(dicyanovinyl)quaterthiophene 2.
- Baert, Francois,Cabanetos, Clment,Lelige, Antoine,Kirchner, Eva,Segut, Olivier,Alvque, Olivier,Allain, Magali,Seo, Gijun,Jung, Sungyeop,Tondelier, Denis,Geffroy, Bernard,Roncali, Jean,Leriche, Philippe,Blanchard, Philippe
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supporting information
p. 390 - 398
(2015/02/02)
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- Synthesis and optical properties of poly(tetramethylsilarylenesiloxane) derivative bearing diphenylcyclopentadithiophene moiety
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The thermal and optical properties of a novel diphenylcyclopentadithiophene-based poly(tetramethylsilarylenesiloxane) derivative (P1), which was prepared via polycondensation of a novel disilanol monomer, i.e., 2,6-bis(dimethylhydroxysilyl)-4,4-diphenylcy
- Hanamura, Hitoshi,Nemoto, Nobukatsu
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p. 6672 - 6679
(2015/02/19)
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- Synthesis and photovoltaic applications of a 4,4′- spirobi[cyclopenta[2,1-b;3,4-b′]dithiophene]-bridged donor/acceptor dye
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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
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supporting information
p. 4642 - 4645
(2013/10/08)
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- In situ monitoring the thermal degradation of PCPDTBT low band gap polymers with varying alkyl side-chain patterns
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The degradation pattern of a series of low band gap PCPDTBT polymers under thermal stress is investigated by in situ UV-vis and FT-IR techniques combined with thermal degradation analysis. Thermogravimetric analysis is used to predetermine the decomposition intervals, revealing that thermolysis occurs in two stages. TG-TD-GC/MS shows that loss of the alkyl side chains predominantly happens within the first temperature regime and degradation of the polymer backbone occurs thereafter. UV-vis spectroscopy is used to monitor the evolution of the optical properties upon heating, reflecting the thermal stability of the conjugated backbone, whereas FT-IR spectroscopy is applied to evaluate the chemical changes under thermal stress, with an emphasis on the polymer periphery. The influence of the side chains and possible defects, dependent on the synthesis protocol applied, on the thermal stability of the final polymers is discussed and is related to the application of said materials in organic photovoltaics.
- Marin, Lidia,Penxten, Huguette,Van Mierloo, Sarah,Carleer, Robert,Lutsen, Laurence,Vanderzande, Dirk,Maes, Wouter
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p. 4912 - 4922
(2013/11/06)
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- Improved photovoltaic performance of a semicrystalline narrow bandgap copolymer based on 4 H-cyclopenta[2,1-b:3,4-b ′]dithiophene donor and thiazolo[5,4-d ]thiazole acceptor units
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A solution processable narrow bandgap polymer composed of alternating 2,5-dithienylthiazolo[5,4-d]thiazole and asymmetrically alkyl-substituted 4H-cyclopenta[2,1-b:3,4-b′]dithiophene units (PCPDT-DTTzTz) was synthesized by Suzuki polycondensation and the donor-acceptor copolymer was thoroughly characterized. Thermal analysis and X-ray diffraction studies disclosed the semicrystalline nature of the material. When blended with PC 71BM and integrated in bulk heterojunction organic solar cells, a moderate power conversion efficiency of 2.43% under AM 1.5 G (100 mW/cm 2) conditions was obtained. However, upon purification of the semiconducting copolymer by preparative size exclusion chromatography, a noticeable rise in power conversion efficiency to 4.03% was achieved. The purified polymer exhibited a relatively high field-effect carrier mobility of 1.0 × 10-3 cm2/(V s). The active layer morphology was explored by atomic force microscopy and transmission electron microscopy studies, showing phase segregation on the nanometer scale.
- Van Mierloo, Sarah,Hadipour, Afshin,Spijkman, Mark-Jan,Van Den Brande, Niko,Ruttens, Bart,Kesters, Jurgen,D'Haen, Jan,Van Assche, Guy,De Leeuw, Dago M.,Aernouts, Tom,Manca, Jean,Lutsen, Laurence,Vanderzande, Dirk J.,Maes, Wouter
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scheme or table
p. 587 - 593
(2012/06/01)
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- 4, 4' disubstituted 4H-cyclopentadithiophene and new methods for synthesising the same
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The present invention relates to a method for the synthesis of a compound having the following general formula: the method comprising the step of reacting, in presence of a diprotic acid having a negative pKa, a compound having the general formula: wherein R1 and R2 are organic groups and wherein X and Y are independently selected from the group consisting of hydrogen, chloro, bromo, iodo, boronic acid, boronate esters, borane, pseudohalogen and organotin. It further relates to compounds so obtained and to compounds resulting from the ring closure of compound (II).
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Page/Page column 35-36
(2012/01/06)
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- A three-step synthetic approach to asymmetrically functionalized 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes
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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.
- Van Mierloo, Sarah,Adriaensens, Peter J.,Maes, Wouter,Lutsen, Laurence,Cleij, Thomas J.,Botek, Edith,Champagne, Benoit,Vanderzande, Dirk J.
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scheme or table
p. 7202 - 7209
(2011/01/12)
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- Double couplings of dibromothiophenes using boronic acids And boronates
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One-pot double couplings of dibromothiophenes have been investigated. Standard Suzuki couplings work well for 2,4-di-bromothiophene, but are much more sensitive to steric effects in the case of 2,3-dibromothiophene. By using the recently reported potassium borates, though, good yields for both dibromothiophene isomers can be achieved. Georg Thieme Verlag Stuttgart · New York.
- Varello, Samantha,Handy, Scott T.
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experimental part
p. 138 - 142
(2009/08/07)
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- PALLADIUM-CATALYZED SYNTHESES OF BI- AND TER-THIOPHENES
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Several heteropolyaromatic compounds containing thiophen rings, of general formula 2, 3, and 5, which are possible antifungal agents, have been synthesized in good yields by Pd-catalyzed reactions.In particular, cross-coupling reactions between 2- or 3-thienylmagnesium bromide and dibromothiophens of general formula 8 in the presence of catalytic amounts of PdCl2, have been used to prepare three isomers (2a, 2b, and 2c) of the naturally occurring 2,2':5',2"-terthiophen, 1, as well as several bromobithienyls of general formula 3.An analogous procedure has been employed for the regioselective synthesis of 3'-bromo-2,2':5',2"-terthiophen, 4, starting from 2-thienylmagnesium bromide, 7a, and 2,3,5-tribromothiophen, 8.On the other hand, heterocyclic esters of general formula 5, which are not readily accessible using conventional organic methods, have been conveniently prepared by Pd-catalyzed ethoxycarbonylation of bromobithienyls 3 under mild experimental conditions.A short synthesis of 5'-(1-propynyl)-2,2'-bithienyl-5-carboxylic acid, 6, a compound isolated from the roots of Arctium lappa, shows the efficacy of the reported Pd-catalyzed reactions.
- Carpita, Adriano,Rossi, Renzo
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p. 575 - 584
(2007/10/02)
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