- Electropolymerized three-dimensional randomly branched edot-containing copolymers
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The potential of 2,2′;3,2″-terthiophene (3T) as branching units in 3D copolymers is presented with EDOT as an example comonomer. Branched EDOT/3T polythiophenes were prepared by electropolymerization, and their electrochemical and optical properties are discussed. Two different approaches were employed: (i) the direct electropolymerization of a novel branched thiophene monomer (3TE3) consisting of a 3T core that contains three outer EDOT end groups and (ii) the electrochemical copolymerization of a EDOT/3T mixture in different ratios from [1:1] to [1:10]. Cyclic voltammetric and vis spectrometric experiments show that the EDOT content within the polymer has a strong influence on the electronic properties of the material: with increasing EDOT content, the HOMO-LUMO gap is decreased. To prove copolymer formation of EDOT and 3T, chemically synthesized reference copolymers of EDOT and 3T were prepared by oxidative coupling using FeCl3, and their optical and electronic properties were compared to those of the electrodeposited films. In addition, the copolymer formation is indicated by the comparison of the electrochemical and spectroscopic results with those of the homopolymers P3T and PEDOT.
- Link, Steffen M.,Scheuble, Martin,Goll, Miriam,Muks, Erna,Ruff, Adrian,Hoffmann, Anke,Richter, Thomas V.,Lopez Navarrete, Juan T.,Ruiz Delgado, M. Carmen,Ludwigs, Sabine
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- Yellow-to-blue switching of indole[3,2-b]carbazole-based electrochromic polymers and the corresponding electrochromic devices with outstanding photopic contrast, fast switching speed, and satisfactory cycling stability
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Three novel π-conjugated indolo[3,2-b]carbazole derivatives, 2,8-di(thiophen-2-yl)-5,11-dioctyl-indolo[3,2-b] carbazole (TICZ), 2,8-bis(4-ethylthiophen-2-yl)-5,11-dioctyl-indolo[3,2-b]carbazole (ETICZ) and 2,8-bis(2-(3,4-ethylenedioxythiophene))-5,11-dioctyl-indolo[3,2-b]carbazole (EDTICZ), were synthesized and electrochemically polymerized to afford the corresponding polymers. The effects of different substituent groups on thiophen units in terms of optical, electrochemical, and electrochromic properties and the performance of electrochromic devices (ECDs) were investigated in detail. Electrochemical and optical analysis demonstrated that incorporation of strong auxochromic groups resulted in polymer PEDTICZ with low oxidation potentials, red-shifted absorption peaks and corresponding narrow band gap values but is unfavorable for incorporating ethyl groups. Spectroelectrochemical studies indicated an evident variation in the absorption spectra as well as significant color changes for all of the polymer films upon application of an external potential. PTICZ had high optical contrast with visible light (58.6%), fast switching speed (0.92 s), and satisfactory coloration efficiency (167 cm2 C?1). Of these three systems, the results for PEDTICZ were next best, and those for PETICZ were third. Also, there was a larger contrast (82.7% and 57.8%) in the NIR region (1500 nm) for the PTICZ and PEDTICZ films, respectively. Along with high coloring efficiencies, these results indicate that these systems are favorable for many NIR applications.
- Xu, Zhen,Zhang, Yuling,Wang, Bozhen,Liu, Zhi,Zhao, Jinsheng,Xie, Yu
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- Structure and photocatalytic activity of a low band gap donor-acceptor-donor (D-A-D) type conjugated polymer: poly(EDOT-pyridazine-EDOT)
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A donor-acceptor-donor (D-A-D) type monomer (3,6-bis(2-(3,4-ethylenedioxy thiophene))pyridazine, EPE) with pyridazine as an intermediate unit (acceptor) and 3,4-ethylenedioxythiophene (EDOT) as a sealing unit (donor) was prepared. The monomer was then polymerized by adjusting various ratios of FeCl3/monomer to prepare a donor-acceptor-donor (D-A-D) type conjugated polymer: poly(EPE). The results from a structural analysis indicated that the conjugation length, doping level, thermal stability, crystallinity, as well as the morphologies of the poly(EPE)s can be affected by the oxidant?:?monomer ratio. The resulting products were characterized by 1H NMR, FT-IR, UV-vis, TGA, XRD, EDX and SEM. Studies were carried out on the photocatalytic performance of the poly(EPE)s for the photocatalytic degradation of different dyes (methylene blue (MB), methyl violet (MU), methyl orange (MO), rhodamine B (RhB) and phenol) (5 mg L?1) under xenon-lamp irradiation, and the same type of light source and different catalysts (poly(EPE)s and PEDOT) on the degradation efficiency of MU were investigated, which showed that poly(EPE) was an effective photocatalyst, and the presence of Fe ions in the polymer matrix played a significant role in enhancing the photocatalytic activity of poly(EPE). Among the poly(EPE)s, the doped poly(EPE)2 ([FeCl3]/[EPE] ratio of 8?:?1) achieved the highest degradation efficiency (95.53%) for MU dye under the simulation of a visible light source for 300 min.
- Yang, Lei,Jamal, Ruxangul,Liu, Fangfang,Wang, Yujie,Abdiryim, Tursun
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- Synthesis and optical properties of some 3,4-(ethylenedioxythiophen-2-yl)-1,2,4-triazine derivatives
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A series of a hybrid oligomers with different combinations of thiophene, EDOT and 1,2,4-triazine rings have been synthesized and characterized. The synthesis of these alternated 1,2,4-triazine derivatives is reported using a straightforward palladium mediated Stille coupling reaction of 2-tri-n-butyltin-3,4-ethylenedioxythiophene with 3-methylsulfanyl-1,2,4-triazine. The molecular structure and the potential optoelectronic properties of the newly obtained compounds were characterized by UV–Vis absorption and emission spectra, X-ray analysis and theoretical calculations at the DFT level.
- Branowska, Danuta,Olender, Ewa,?wi?tochowska, Monika,Karczmarzyk, Zbigniew,Wysocki, Waldemar,Cichosz, Iwona,Wo?na, Agnieszka,Urbańczyk-Lipkowska, Zofia,Kalicki, Przemys?aw,Gil, Micha?
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- A Free-standing electrochromic material of poly(5,7-bis(2-(3,4-ethylenedioxy)thienyl)-indole) and its application in electrochromic device
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Free-standing poly(5,7-bis(2-(3,4-ethylenedioxy)thienyl)-indole) (PETI) was electrochemically obtained from 5,7-bis(2-(3,4-ethylenedioxy)thienyl)-indole (ETI) prepared by Stille coupling reaction of 5,7-dibromoindole and 3,4-ethylenedioxythiophene. For comparison, poly(5,7-bis(2-thiophene)-indole) was also electrosynthesized from 5,7-bis(2-thiophene)-indole (BTI) which was prepared from the 5,7-dibromoindole and thiophene. Characterizations of ETI and BTI were performed by cyclic voltammetry, scanning electron microscopy, 1H NMR, and 13C NMR spectroscopy. Spectroelectrochemical studies showed PETI had better electrochromic properties and showed two different colors (brown and blue-violet) under various potentials with better maximum contrast (ΔT%) and coloration efficiency (CE). An electrochromic device (ECD) based on PETI and poly(3,4-ethylenedioxythiophene) (PEDOT) was also constructed and characterized. This ECD had fast response time, high CE, better optical memory, and long-term stability. These results indicated that PETI had potential applications for ECD.
- Yang, Xiaoyan,Liu, Changlong,Guo, Jiabao,Wang, Ling,Nie, Guangming
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- Evidence for the contribution of sulfur-bromine intramolecular interactions to the self-rigidification of thiophene-based π-conjugated systems
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Bithiophene associating 3,4-ethylenedioxythiophene and 3-bromothiophene, and the corresponding polymer exhibit self-rigidified structures of the conjugated backbones resulting from the association of S-Br and S-O non-bonded intramolecular interactions. Th
- Hergue, Noemie,Leriche, Philippe,Blanchard, Philippe,Allain, Magali,Gallego-Planas, Nuria,Frere, Pierre,Roncali, Jean
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- Intramolecular charge transfer (ICT) of a chiroptically active conjugated polymer showing green colour
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A donor-acceptor type achiral monomer 4,7-bis(2,3-dihydrothieno[3,4-b]-1,4-dioxin-5-yl)-2,1,3-benzothiadiazole was synthesised and electrochemically polymerised in a cholesteric liquid crystalline (CLC) medium. This film exhibits a fingerprint pattern under the polarised optical microscopic observation. A possible mechanism of the fingerprint structure formation through a procedure of electrochemical polymerisation in a CLC medium is presented. The preparation of chiral polymer films even from achiral monomers is demonstrated. The film shows green colour in the reduced state and blue in the oxidised state. Changes in colour and CD signals of the film are repeatable with electrochemical oxidation and reduction. The presence of radical cations in the chiral environment, referred to as chiralions, distributed along chiral polymer chains is proposed.
- Kawashima, Hirotsugu,Kawabata, Kohsuke,Goto, Hiromasa
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- Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor-acceptor-donor type polymers
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A new benzimidazole unit, 4′-(tert-butyl)spiro[benzo[d]imidazole-2, 1′-cyclohexane] was synthesized and coupled with different donor units like 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT) via Stille coupling. The donor-acceptor-donor (D-A-D) ty
- Ozelcaglayan, Ali Can,Sendur, Merve,Akbasoglu, Naime,Apaydin, Dogukan Hazar,Cirpan, Ali,Toppare, Levent
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- Highly fluorescent triazolopyridine-thiophene D-A-D oligomers for efficient pH sensing both in solution and in the solid state
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Conjugated fluorophores have been extensively used for fluorescence sensing of various substances in the field of life processes and environmental science, due to their noninvasiveness, sensitivity, simplicity and rapidity. Most existing conjugated fluorophores exhibit excellent light-emitting performance in dilute solutions, but their properties substantially decrease or even completely vanish due to severe aggregation quenching in the solid state. Herein, we synthesize a series of triazolopyridine-thiophene donor-acceptor-donor (D-A-D) type conjugated molecules with high absolute fluorescence quantum yields (ΦF) ranging from 80% to 89% in solution. These molecules also show unusual light-emitting properties in the solid state with ΦF of up to 26%. We find that owing to the protonation-deprotonation process of the pyridine ring, these compounds display obvious changes in both fluorescence wavelength and intensity upon addition of acids, and these changes can be readily recovered by the successive introduction of bases. By harnessing this phenomenon, we further show that these fluorophores can be employed for efficient and reversible fluorescence sensing of hydrogen ions in a broad pH range (0.0-7.0). With the fabrication of pH testing papers and ink-printed complex patterns including butterflies and letters on substrates, we demonstrate the application of such sensors to fluorescence indication or solid state pH detection for real samples such as volatile acidic/basic gas and water-quality analysis.
- Jian, Nannan,Qu, Kai,Gu, Hua,Zou, Lie,Liu, Ximei,Hu, Faqi,Xu, Jingkun,Yu, Yan,Lu, Baoyang
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- Tuning band structures of dyes for dye-sensitized solar cells: Effect of different π-bridges on the performance of cells
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Three organic dyes (LJ101, LJ102, and LJ103) with different π-bridges such as thiophene, 3-hexylthiophene and 3, 4-ethyldioxythiophene, were prepared and applied for the dye-sensitized solar cells (DSSCs). The effect of the different π-bridges on the phot
- Liu, Jing,Yang, Xichuan,Zhao, Jinxia,Sun, Licheng
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- Synthesis, characterization and photovoltaic properties of a low-bandgap platinum(II) polyyne functionalized with a 3,4-ethylenedioxythiophene-benzothiadiazole hybrid spacer
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The synthesis, characterization and optical spectroscopy of a deep blue platinum(II) polyyne functionalized with the (3,4-ethylenedioxythiophene)-benzothiadiazole hybrid spacer (P1) and its dinuclear platinum molecular model complex (M1) are described. This metalated polymer P1 exhibits good thermal stability and possesses a narrow bandgap of 1.76 eV. Optical spectroscopic measurements of these materials reveal a substantial donor-acceptor interaction along the rigid backbone of the organometallic polyynes through the interaction of metal center and the conjugated tricyclic ligand. Preliminary study shows that P1: methanofullerene acceptor blend can be used as an active layer of bulk-heterojunction polymer solar cells. Photoexcitation of this blend layer in some yet-to-be optimized cells results in a photo-induced electron transfer from the π-conjugated metallopolyyne electron donor to [6,6]-phenyl C61-butyric acid methyl ester with a power conversion efficiency (PCE) close to 0.30% under air mass (AM1.5) simulated solar illumination. The power dependencies of the solar cell parameters (including the short-circuit current density, open-circuit voltage, fill-factor and PCE) were also studied.
- Wong, Wai-Yeung,Wang, Xingzhu,Zhang, Hai-Liang,Cheung, Kai-Yin,Fung, Man-Kin,Djuri?i?, Aleksandra B.,Chan, Wai-Kin
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- Effect of conjugated core building block dibenzo[a,c]phenazine unit on π-conjugated electrochromic polymers: Red-shifted absorption
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A comparative investigation was undertaken for the electrosynthesis and electrochemical properties of three different electroactive polymers having a conjugated core building block, dibenzo[a,c]phenazine. A series of monomers has been synthesized as regards to thiophene based units; thiophene, 3-hexyl thiophene, and 3,4-ethylenedioxythiophene. The effects of different donor substituents on the polymers' electrochemical properties were examined by cyclic voltammetry. Introducing highly electron-donating (ethylene dioxy) group to the monomer enables solubility while also lowering the oxidation potential. The planarity of the monomer unit enhances π-stacking and consequently lowering the Eg from 2.4 eV (PHTP) to 1.7 (PTBP). Cyclic voltammetry and spectroelectrochemical measurements revealed that 2,7-bis(4-hexylthiophen-2-yl) dibenzo[a,c]phenazine (HTP) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5- yl)dibenzo[a,c]phenazine (TBP) possessed electrochromic behavior. The colorimetry analysis revealed that while PTBP have a color change from red to blue, PHTP has yellow color at neutral state and blue color at oxidized state. Hence the presence of the phenazine derivative as the acceptor unit causes a red shift in the polymers' absorption to have a blue color.
- Unver, Elif Kose,Tarkuc, Simge,Udum, Yasemin Arslan,Tanyeli, Cihangir,Toppare, Levent
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- Design of twisted conjugated molecular systems towards stable multi-colored electrochromic polymers
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Promising advancement of conjugated polymers in electrochromic devices require to design high-performance electrochromic polymers with rich color conversion and long-term stability under cyclic electrical loads. Here we report a new strategy in developing multi-colored electrochromic polymers with good stability via twisted conjugated molecular engineering. A series of twisted hybrid precursors are synthesized by coupling ortho-alkylenedioxybenzenes with EDOT units, and their corresponding polymers are facilely electrosynthesized at relatively low polymerization potentials. The structure-property relationships of such ortho-alkylenedioxybenzene-EDOT hybrid precursors and polymers are systematically elucidated via DFT calculations, spectral, morphological, electrochemical and spectroelectrochemical analysis, etc. We demonstrate that the dihedral angle between ortho-alkylenedioxybenzenes and EDOT moieties can substantially affect the electrochemical and electrochromic properties of polymers. As the dihedral angle and electron cloud density increases, these hybrid polymers display distinct multiple color switching nature and good overall performance including high coloration efficiency (>200 cm2 C?1), decent optical contrast (>45percent), fast switching (1 s), and excellent switching stability (96percent of optical contrast after 3500 cycling) under cyclic electrical loads. With these findings, this work will provide novel insights for rational design of stable and highly efficient multi-colored electrochromic polymers.
- Gu, Hua,Hu, Faqi,Jian, Nannan,Lin, Kaiwen,Liu, Ximei,Lu, Baoyang,Wu, Tao,Xu, Jingkun,Xue, Yu
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- Pyrazine-EDOT D-A-D type Hybrid Polymer for Patterned Flexible Electrochromic Devices
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Two donor-acceptor type pyrazine-EDOT hybrid polymers are developed as high performance electrochromic materials and employed to fabricate flexible electrochromic devices via electropolymerization patterning. By coupling EDOT with pyrazine at 2,5-positions, the resultant precursor 2,5-BEP can facilely electropolymerize to yield high quality pyrazine-EDOT hybrid polymer films with excellent electrochemical stability. Spectroelectrochemistry and kinetic studies demonstrate that as-formed pyrazine-EDOT hybrid polymer exhibits reversible color-changing nature from purple to gray with high coloration efficiency (134 cm2 C?1), fast response time (0.2 s) and high optical contrast (> 55percent) over a wide wavelength range of 800–2200 nm in near-infrared (NIR) region. To harness its excellent electrochromic performance as well as the ease of electropolymerization patterning, we fabricate patterned flexible electrochromic devices (ECDs) via facile electropolymerization and such ECDs display reversible color changes with decent optical stability (25percent reduction in optical contrast upon 1000 cycling) and excellent mechanical stability (9.6percent reduction in optical contrast upon bending 5000 cycles). The excellent electrochromic performance and stability of pyrazine-EDOT hybrid polymers as well as their-based ECDs make them good candidates towards near infrared electrochromic applications.
- Hu, Faqi,Jian, Nannan,Lin, Kaiwen,Liu, Ximei,Lu, Baoyang,Qu, Kai,Wu, Tao,Xu, Jingkun,Xue, Yu,Zhu, Xiukai
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- Poly[3,4-ethylene dioxythiophene (EDOT)-co-1,3,5-tri[2-(3,4-ethylene dioxythienyl)]-benzene (EPh)] copolymers (PEDOT-co-EPh): Optical, electrochemical and mechanical properties
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PEDOT-co-EPh copolymers with systematic variations in composition were prepared by electrochemical polymerization from mixed monomer solutions in acetonitrile. The EPh monomer is a trifunctional crosslinking agent with three EDOTs around a central benzene ring. With increasing EPh content, the color of the copolymers changed from blue to yellow to red due to decreased absorption in the near infrared (IR) spectrum and increased absorption in the visible spectrum. The surface morphology changed from rough and nanofibrillar to more smooth with rounded bumps. The electrical transport properties dramatically decreased with increasing EPh content, resulting in coatings that either substantially lowered the impedance of the electrode (at the lowest EPh content), leave the impedance nearly unchanged (near 1% EPh), or significantly increase the impedance (at 1% and above). The mechanical properties of the films were substantially improved with EPh content, with the 0.5% EPh films showing an estimated 5× improvement in modulus measured by AFM nanoindentation. The PEDOT-co-EPh copolymer films were all shown to be non-cytotoxic toward and promote the neurite outgrowth of PC12 cells. Given these results, we expect that the films of most interest for neural interface applications will be those with improved mechanical properties that maintain the improved charge transport performance (with 1% EPh and below). This journal is
- Ouyang, Liangqi,Kuo, Chin-Chen,Farrell, Brendan,Pathak, Sheevangi,Wei, Bin,Qu, Jing,Martin, David C.
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- Design and synthesis of 9,9-dioctyl-9H-fluorene based electrochromic polymers
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Two novel heterocycle-fluorene-heterocycle monomers, 2,2′-(9,9-dioctyl-9H-fluorene-2,7-diyl)dithiophene (Th-F-Th) and 5,5′-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(2,3-dihydrothieno[3,4-b][1,4]dioxine) (EDOT-F-EDOT), were synthesized via Stille coupling reaction and electropolymerized to form corresponding polymers P(Th-F-Th) and P(EDOT-F-EDOT). Furthermore, the optoelectronic properties of the obtained monomers and polymers were explored using cyclic voltammetry (CV), UV-vis, and emission spectra and in situ spectroelectrochemical techniques. The band gap values of monomers calculated by DFT were 3.75 eV for EDOT-F-EDOT and 4.03 eV for Th-F-Th, while that of P(EDOT-F-EDOT) and P(Th-F-Th) were brought down to 1.70 and 2.10 eV, respectively. Both polymers exhibited excellent redox activity and electrochromic performance. P(EDOT-F-EDOT) exhibited a maximum optical contrast of 25.8% at 500 nm in visible region with a response time of 1.2 s. In addition, the coloration efficiency of P(EDOT-F-EDOT) was calculated to be 220 cm2 C-1.
- Jiang, Qinglin,Zhen, Shijie,Mo, Daize,Lin, Kaiwen,Ming, Shouli,Wang, Zhipeng,Liu, Congcong,Xu, Jingkun,Yao, Yuanyuan,Duan, Xuemin,Zhu, Danhua,Shi, Hui
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- Thiophene derivative as well as synthesis method and application thereof
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The invention discloses a thiophene derivative (E2SBFE2) as shown in a formula 1, 2,7-bis(2,2',3,3'-tetrahydro-5,5'-dithieno[3,4-b][1,4]dioxene)-9,9'-spirobifluorene, a synthetic method of the thiophene derivative and application of the thiophene derivative as a polymer emulsion additive. The E2SBFE2 can be used as an additive to be compounded with a PVDC emulsion to prepare a composite emulsion E2SBFE2-coated PVDC, and the composite emulsion is particularly suitable for being smeared on hard sheets such as PVC and the like to prepare composite hard sheets and has the advantage of high yellowing resistance.
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Paragraph 0029; 0034-0036
(2021/06/13)
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- Indole derivative-EDOT compound as well as preparation and application thereof
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The invention provides an indole derivative-EDOT compound as well as preparation and application thereof, the compound takes an indole derivative as a central core and EDOT as a peripheral group, andthe structure of the compound is shown as a formula (1). The indole derivative-EDOT compound has the beneficial effects that (1) the indole derivative-EDOT compound has a reticular space structure andis subjected to electrochemical polymerization to form a film, so that the obtained film has a relatively large specific surface area and also has good electrochemical properties such as electrochromism and the like; (2) a film prepared by taking the compound as a monomer through electro-chemistry can be randomly switched from yellow to green (0.6 V) and blue (0.9 V), the optical contrast ratio is 20%-30%, the response time is 0.5-2 seconds, and the compound shows relatively good spectral electrochemical stability in any wave band, and is a low-voltage electrochromic material capable of realizing color change.
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Paragraph 0027-0029
(2020/12/30)
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- EDOT-quinoxaline-EDOT derivative and preparation method and application thereof
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The invention relates to an EDOT-quinoxaline-EDOT derivative, a preparation method of the EDOT-quinoxaline-EDOT derivative and application of an electrochemical polymerized film of the EDOT-quinoxaline-EDOT derivative as a novel photoelectric functional m
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Paragraph 0045-0046
(2019/08/26)
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- Perovskite hole transport material based on triptycene mother nucleus and preparation method thereof
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The present invention discloses a perovskite hole transport material based on a triptycene mother nucleus and a preparation method thereof. The material is 2,6,14-tri(50-(N,N-bi(4-methoxyphenyl)aminophenol-4-yl)-3,4-ethylenedioxythiophene-2-yl)-triptycene. The preparation method has the advantages of mild synthesis conditions, simple steps, cheap and easily obtained synthetic raw materials, and low synthesis costs. The prepared material has a good thermal stability, solubility and film forming property. An ultraviolet-visible light absorption spectrum indicates the hole transport material based on the triptycene mother nucleus has a large conjugate structure, has a more suitable HOMO level (-5.08 eV) than that of a mainstream hole transport material Spiro-MeOTAD, and provides a strong driving force for hole transporting. The carrier mobility of the material measured by a space charge limiting current method is 8x10cm.Vs. The perovskite hole transport material has potential.
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Paragraph 0069-0071
(2018/11/03)
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- D-D-pi-A structured photosensitive dye using carbazole and triphenylamine as two-stage electron donors, and preparation method and application thereof
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The invention discloses a D-D-pi-A structured photosensitive dye using carbazole and triphenylamine as two-stage electron donors. The photosensitive dye uses triphenylamine and carbazole as electron donors, 3,4-ethylenedioxythiophene or thiophene as a pi conjugated bridge and cyanoacetic acid as an electron acceptor. The invention also provides a preparation method of the photosensitive dye, and an application of the photosensitive dye in dye-sensitized solar cells. The photosensitive dye has various structures, and has a photoelectric conversion efficiency reaching up to 6%, and the preparation method has the advantages of simplicity, easiness in process control, low cost, and friendliness to the environment. The preparation method is suitable for preparing the D-D-pi-A structured photosensitive dye using carbazole and triphenylamine as two-stage electron donors, and the prepared photosensitive dye is suitable for being applied to the dye-sensitized solar cells.
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Paragraph 0145; 0148; 0150; 0151
(2018/11/03)
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- CHARGE-TRANSPORTING VARNISH, CHARGE-TRANSPORTING THIN FILM, ORGANIC ELECTROLUMINESCENT ELEMENT AND CHARGE-TRANSPORTING THIN FILM MANUFACTURING METHOD OF
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The present invention provides charge transporting varnish which can be sintered at a low temperature of less than 200 DEG C. A charge transporting thin film manufactured under such sintering conditions has high flatness and high charge transporting ability. If the charge transporting thin film is applied to an organic EL device, excellent properties of the EL device can be exerted. The charge transporting varnish contains charge transporting material, a dopant and an organic solvent, and is characterized in that the dopant includes heteropoly acid and at least one selected from halogenated tetracyanoquinodimethane and halogenated or cyano benzoquinone.
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Paragraph 0098; 0099
(2019/01/05)
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- Tetraphenylmethane or silane-based compound as well as preparation method and application thereof
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The invention provides a tetraphenylmethane or silane-based compound shown in formula (I), a preparation method of the tetraphenylmethane or silane-based compound and application of the tetraphenylmethane or silane-based compound in synthesizing an electrochromic material membrane as a monomer. As the tetraphenylmethane or silane-based compound has a space structure of tetrahedral tetrad, through membrane formation with electrochemcial polymerization, the obtained membrane expresses larger specific surface area and good electrochemical performance such as electrochromism and the like at the same time. The contrast of the membrane is 30-80 percent, the response time of the membrane is between 0.5s and 6s, the contrast and the response time both express reasonable electrochemcial stable activity, and experimental results show that the material is a potential electrochromic material. The formula of the tetraphenylmethane or silane-based compound is shown in the description.
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Paragraph 0041; 0042; 0043; 0053; 0054; 0055
(2017/10/09)
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- Photosensitive dye of D-D-pi-A structure with triphenylamine as two-electron donor as well as preparation method and application of photosensitive dye
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The invention discloses a photosensitive dye of a D-D-pi-A structure with triphenylamine as a two-electron donor as well as a preparation method and application of the photosensitive dye. According to the photosensitive dye, triphenylamine is adopted as the two-electron donor, 3,4-ethylene dioxythiophene is adopted as a pi conjugate bridge and cyanoacetic acid is adopted as an electron donor, the chemical structural formula of the photosensitive dye is as shown in the specification, and in the formula, R1 is a group of vinyl, butadienyl or p-divinyl benzene, and R2 is methoxy or hexyloxy. The photosensitive dye disclosed by the invention is diverse in structure and is capable of improving the dyeing property, and thus relatively high photoelectric conversion efficiency is achieved. The invention further provides a corresponding preparation method of the photosensitive dye. The photosensitive dye is prepared from a primary electron donor and a secondary electron donor of different structures through reaction. The preparation method is simple in process, low in preparation cost and environmental-friendly. The invention further provides corresponding application of the photosensitive dye. The photosensitive dye can be used for preparing dye-sensitized solar cells, and tests show about 6% of photoelectric conversion efficiency is achieved.
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Paragraph 0070; 0074; 0075
(2017/11/16)
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- Star-shaped triphenylamine derivative, and preparation method and applications thereof
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The invention discloses a star-shaped triphenylamine derivative, and a preparation method and applications thereof. According to the preparation method, 3,4-ethoxylene dioxy thiophene is reacted with n-butyllithium and tributyl tin chloride successively so as to obtain an intermediate 1; under the catalytic action of palladium, the intermediate 1 is reacted with tris(4-bromophenyl)amine so as to obtain an intermediate 2; under the action of phosphorus oxychloride, the intermediate 2 is reacted with N,N-dimethylformamide so as to obtain an intermediate 3; and at last, the intermediate 3 is reacted with malononitrile in the presence of triethylamine so as to obtain a finished product N,N,N-tri[4-(5-dicyanovinyl-3,4-ethenyldioxy-2-thienyl) phenyl]amine. The star-shaped triphenylamine derivative is possible to be used as a high efficiency organic photovoltaic cell electron donor material because of the unique molecular structure and large conjugated system.
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Paragraph 0025; 0026
(2017/07/20)
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- Synthesis and Electrochromic Properties of Star-Shaped Oligomers with Phenyl Cores
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A series of star-shaped conjugated oligomers, 1,3,5-tri(2′-thienyl) benzene (3TB), 1,3,5-tri(3′,4′-ethylenedioxythienyl) benzene (3EB), 1,3,5-tri[5′,2“-(3”,4“-ethylenedioxy-thienyl)-2′-thienyl] benzene (3ETB), and 1,3,5-tri[5′,2”-(3“,4”-ethylenedioxy-thie
- Zeng, Jinming,Zhang, Xiaoyuan,Zhu, Xiaoting,Liu, Ping
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supporting information
p. 2202 - 2206
(2017/09/11)
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- Poly (triphenylamine-fluorenylmethylchloroformate) dye and its application
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The invention discloses a poly(triphenylamine-fluorene) dye and its application. The poly(triphenylamine-fluorene) dye is prepared through a Stille coupling reaction of a monomer having a triphenylamine structure and a monomer having a fluorene structure. The prepared poly(triphenylamine-fluorene) dye has a triphenylamine and fluorene composite donor unit structure, and can be applied in the production of dye-sensitized solar cells in order to obtain dye-sensitized solar cells with high current density and high photoelectric conversion rate.
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Paragraph 0076; 0078; 0079; 0080
(2017/02/28)
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- Side-chain engineering of green color electrochromic polymer materials: Toward adaptive camouflage application
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The syntheses of adaptive camouflage devices based on novel side-chain engineered organic electrochromic materials have been demonstrated. Herein we report a molecule engineering approach for the tuning and syntheses of green-brown switchable electrochrom
- Yu, Hongtao,Shao, Shan,Yan, Lijia,Meng, Hong,He, Yaowu,Yao, Chao,Xu, Panpan,Zhang, Xiaotao,Hu, Wenping,Huang, Wei
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supporting information
p. 2269 - 2273
(2016/04/04)
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- Can aliphatic anchoring groups be utilised with dyes for p-type dye sensitized solar cells?
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A series of novel laterally anchoring tetrahydroquinoline derivatives have been synthesized and investigated for their use in NiO-based p-type dye-sensitized solar cells. The kinetics of charge injection and recombination at the NiO-dye interface for these dyes have been thoroughly investigated using picosecond transient absorption and time-resolved infrared measurements. It was revealed that despite the anchoring unit being electronically decoupled from the dye structure, charge injection occurred on a sub picosecond timescale. However, rapid recombination was also observed due to the close proximity of the electron acceptor on the dyes to the NiO surface, ultimately limiting the performance of the p-DSCs.
- Hao, Yan,Wood, Christopher J.,Clark, Charlotte A.,Calladine, James A.,Horvath, Raphael,Hanson-Heine, Magnus W. D.,Sun, Xue-Zhong,Clark, Ian P.,Towrie, Michael,George, Michael W.,Yang, Xichuan,Sun, Licheng,Gibson, Elizabeth A.
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p. 7708 - 7719
(2016/05/24)
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- ORGANIC DYE FOR A DYE-SENSITIZED SOLAR CELL
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Organic dye for a dye-sensitized solar cell (DSSC) comprising at least one electron-acceptor unit and at least one π-conjugated unit. Said organic dye is particularly useful in a dye-sensitized photoelectric transformation element which, in its turn, can be used in a dye-sensitized solar cell (DSSC).
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Paragraph 0157; 0158; 0159
(2016/10/04)
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- Oligothiophene derivative and its preparation method
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The invention relates to an oligothiophene derivative and a preparation method thereof. The preparation method of the oligothiophene derivative mainly comprises the following steps of: dissolving 3TB into dichloromethane, adding NBS (N-bromosuccinimide),
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Paragraph 0020
(2017/01/23)
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- Synthesis and electro-optical properties of new conjugated hybrid polymers from EDOT end-capped dibenzothiophene and dibenzofuran
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Two novel EDOT end-capped monomers, namely, 2,8-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-dibenzothiophene (DBT-EDOT), and 2,8-di-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl-dibenzofuran (DBF-EDOT), were synthesised via Stille coupling and electropolymerised to form conjugated polymers P(DBT-EDOT) and P(DBF-EDOT). The monomers exhibited blue-light-emitting characteristics, and DFT calculations revealed band gap values of 4.20 eV for DBT-EDOT and 4.34 eV for DBF-EDOT, while those of the corresponding polymers were brought down to 2.46 eV for P(DBT-EDOT) and 2.58 eV for P(DBF-EDOT), respectively. Moreover, both of the polymers displayed good electrochromic properties with colour switching between yellow in the reduced state and purple in the oxidised state. Structure characterisation and properties of monomers and as-formed polymers using FTIR spectroscopy, UV-vis spectroscopy, surface morphology, fluorescence spectroscopy, electrochemistry, and spectroelectrochemistry, together with structure-property relationships, were systematically investigated and comprehensively discussed.
- Lin, Kaiwen,Zhen, Shijie,Ming, Shouli,Xu, Jingkun,Lu, Baoyang
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p. 2096 - 2105
(2015/03/18)
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- Synthesis and structure-activity relationship of amidine derivatives of 3,4-ethylenedioxythiophene as novel antibacterial agents
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9 new amidine derivatives of 3,4-ethylenedioxythiophene were synthesized.27 amidines were tested for their antibacterial activities.Bis-phenyl derivatives show highest activity against sensitive and resistant strains.Bis-benzimidazole derivative had the b
- Stoli?, Ivana,?ip?i? Paljetak, Hana,Peri?, Mihaela,Matija?i?, Mario,Stepani?, Vi?nja,Verbanac, Donatella,Baji?, Miroslav
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- A D-π-A-π-A type dye for highly efficient dye-sensitized solar cells
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We synthesized a D-π-A-π-A type dye and demonstrated its application in dye-sensitized solar cells (DSSCs). This D-π-A-π-A type dye, named C321, consisted of a triphenylamine as a donor, a 3,4-ethylenedioxythiophene (EDOT) as a π-bridge, and a benzothiazo
- Du, Chao-Feng,Jiang, Lei,Sun, Lei,Huang, Nian-Yu,Deng, Wei-Qiao
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p. 37574 - 37580
(2015/07/15)
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- Synthesis of EDOT -containing polythiophenes and their properties in relation to the composition ratio of EDOT
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Polythiophenes composed of 3,4-ethylenedioxythiophene (EDOT) and 3-hexylthiophene with different composition ratios of EDOT in the repeat unit of the polymer backbone are synthesized by polycondensation reactions. The optical and electrochemical properties of the polymers are compared with those of poly(3,4-ethylenedioxythiophene) and poly(3-hexylthiophene), and they are found to be well correlated with the EDOT composition ratio. In addition, the charge transport properties of the polymer films, measured using the in situ conductivity technique, are discussed in terms of the EDOT composition ratio, regioregularity, and the doping level.
- Imae, Ichiro,Ogino, Ryo,Tsuboi, Yoshiaki,Goto, Tatsunari,Komaguchi, Kenji,Harima, Yutaka
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p. 84694 - 84702
(2015/10/28)
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- Unusual doping of donor-acceptor-type conjugated polymers using lewis acids
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Conjugated polymers that can undergo unusual nonoxidative doping were designed. A series of polymers based on donor-acceptor-donor (DAD) moieties 2,1,3-benzoselenadiazole, 2,1,3-benzothiadiazole, 2,1,3-benzoxadiazolebenzo[2,1, 5]oxodiazole, and 2-hexylbenzotriazole as acceptor fragments and 3,4-ethylenedioxyselenophene (EDOS) and 3,4-ethylenedioxythiophene (EDOT) as donor fragments was prepared. When the studied polymers were reacted with Lewis acids and bases, notable optical switching and conductivity changes were observed, evidencing the exceptional case of efficient nonoxidative doping/dedoping. Remarkably, in previously reported works, coordination of Lewis acids causes band gap shift but not doping of the conductive polymer, while in the present study, coordination of Lewis acid to highly donating EDOT and EDOS moieties led to polymer doping. The polymers show remarkable stability after numerous switching cycles from neutral to doped states and vice versa and can be switched both electrochemically and chemically. The reactivity of the prepared polymers with Lewis acids and bases of different strengths was studied. Calculation studies of the Lewis acid coordination mode, its effect on polymer energies and band gap, support the unusual doping. The reported doping approach opens up the possibility to control the conjugation, color change, and switching of states of conjugated polymers without oxidation.
- Poverenov, Elena,Zamoshchik, Natalia,Patra, Asit,Ridelman, Yonatan,Bendikov, Michael
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p. 5138 - 5149
(2014/04/17)
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- Tuning the optoelectronic properties of polyfuran by design of furan-EDOT monomers and free-standing films with enhanced redox stability and electrochromic performances
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Most recently, conjugated oligo-/polymers containing furan have regained attention due to their unique properties and promising application in organic electronics. Herein, to acquire a thorough fundamental understanding of the electrosynthesis and properties of furan-EDOT copolymers from different initial monomers, the synthesis and electropolymerization performances of furan-EDOT monomers, namely 5-(furan-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin (EDOT-Fu), 5,7-di(furan-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin (Fu-EDOT-Fu), and 2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)furan (EDOT-Fu-EDOT), were comprehensively reported and the effect of different monomers on the structure and properties of the resulting polymers obtained under optimized electrical conditions were systematically evaluated. The monomers exhibit good blue-green photoluminescence with quantum yields ranging from 0.5 to 40%, which may be used as building blocks for rational design of fluorescent conjugated systems. The onset oxidation potential ranged from 0.78 V-0.45 V with the incorporation of EDOT unit in monomer chain, thus leading to the facile electrodeposition of free-standing films with improved optoelectronic properties in comparison with polyfuran. The obtained copolymers featured the advantageous combination of polyfuran and PEDOT, such as higher fluorescence and better planarity of polyfuran, transparency and excellent redox stability of PEDOT. Structure characterization and properties of the as-formed copolymer films from different initiative monomers, including FT-IR, UV-vis, TG, fluorescence, surface morphology and electrochromic properties, etc., were systematically investigated and comparatively discussed.
- Zhen, Shijie,Xu, Jingkun,Lu, Baoyang,Zhang, Shimin,Zhao, Li,Li, Jie
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p. 666 - 678
(2015/02/19)
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- ORGANIC DYE, DYE-SENSITIZED METAL OXIDE SEMICONDUCTOR ELECTRODE AND DYE-SENSITIZED SOLAR CELL
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An object of the present invention is to provide a dye sensitizer for a solar cell having stability and an excellent conversion efficiency. There is provided a dye sensitizer represented by the following general formula, to which a donor site (D) and an acceptor site (A) are bound via linkers (L1)n and (L2)n: (φ is an aromatic ring with or without heteroatom(s); D is a triphenylamine derivative, a carbazole derivative, a coumarine derivative or an indoline derivative; A is an organic residue having an acidic group; each of L1 and L2 is an optionally substituted divalent alkenyl group, aromatic group or heterocyclic group, and n represents an integer of 0 to 3).
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Page/Page column 34-35
(2013/03/26)
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- HIGHLY-FLUORESCENT AND PHOTO-STABLE CHROMOPHORES FOR ENHANCED SOLAR HARVESTING EFFICIENCY
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The invention provides highly fluorescent materials comprising a single (n=0) or a series (n=1, 2, etc.) of benzo heterocyclic systems. The photo-stable highly luminescent chromophores are useful in various applications, including in wavelength conversion films. Wavelength conversion films have the potential to significantly enhance the solar harvesting efficiency of photovoltaic or solar cell devices.
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Paragraph 0159
(2013/04/10)
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- Functionalized γ(p)-conjugated polymers, based on 3,4-alkylenedioxythiophene
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Polythiophenes of the formula II Z=alky, aryl or alkylaryl, u=0 or 1, m=0 to 5, n=2 to 500, X=(CH2)p+q or (CH2)p—O—(CH2)q, p, q are each, independently of one another, from 0 to 10 and R, R′ are identical or different and are each, independently of one another, H, a linear or branched C1-C18 alkyl or alkoxy radical or a linear or branched C1-C18 alkylsulfonate or alkoxysulfonate radical, can be modified via the active ester function and have excellent electrical and optical properties.
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Page/Page column 2; 6
(2010/11/30)
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- Bithienylnaphthalene- and bis(3,4-ethylenedioxythienyl)naphthalene-based monomers and polymers
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Provided are novel, electropolymerizable monomers of the formulae: wherein R1,R2and R3are selected from the group consisting of —H, —O(CH2)nCH3, wherein n has a value of 0 to 11 and m has a value of 1 to 4, and wherein no more than one of R2and R3is —H. Also provided are polymers resulting from the electropolymerization of these monomers.
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Page column 7
(2010/01/31)
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- Electro-active monomers comprised of aniline-thiophene units
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Provided are novel, electropolymerizable monomers of the formulae:
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