- Highly efficient, iodine-free dye-sensitized solar cells with solid-state synthesis of conducting polymers
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A solid-state polymerizable conductive monomer with good conductivity and penetration to the photoelectrode is introduced to iodine-free, solid-state dye-sensitized solar cells (DSSCs) using an easily accessible and widely applicable fabrication method. A conducting polymer as a hole transporting material effectively penetrates into the TiO2 pores and polymerizes with heating to mild temperatures. The fabricated DSSCs exhibited the highest energy conversion efficiency of 5.4% in N719 dye.
- Koh, Jong Kwan,Kim, Jeonghun,Kim, Byeonggwan,Kim, Jong Hak,Kim, Eunkyoung
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- Electromagnetic interference shielding properties of solid-state polymerization conducting polymer
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Poly(3,4-ethylenedioxythiophene) (PEDOT) has been synthesized through a facile solid-state polymerization (SSP) approach. The polymerization was simply initiated by sintering the monomer, 2,5-dibro-3,4-ethylenedioxythiophene (DBEDOT), at a temperature of 80 °C. A high performance shield for electromagnetic interference (EMI) protection based on this SSP-PEDOT has been developed. The SSP-PEDOT with a heating time of 24 hours has the maximum value of the dielectric loss tangent (tanδε) in the frequency range of 2-18 GHz, which revealed that this sample has the best electromagnetic energy absorption ability. When the thickness of the sample reached 2 mm, the bandwidth with the reflection loss (RL) deeper than -10 dB was nearly 5.9 GHz (from 10.0 GHz to 15.9 GHz), and the maximum value of RL was about -50.1 dB at 11.2 GHz. The SSP-PEDOT with a heating time of 1 hour had the best EMI shielding effectiveness (SEtotal) in the entire frequency range of 2-18 GHz, which was almost contributed to the reflection from the material surface (SER). These results demonstrated that SSP initiated at low temperature shows multi-practical EMI shielding application in the areas of military camouflage and electronic devices protection. the Partner Organisations 2014.
- Wu, Fan,Xu, Zhuanghu,Wang, Yuan,Wang, Mingyang
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- Vortex fibril structure and chiroptical electrochromic effect of optically active poly(3,4-ethylenedioxythiophene) (PEDOT*) prepared by chiral transcription electrochemical polymerisation in cholesteric liquid crystal
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Chiroptical electroactive poly(3,4-ethylenedioxythiophene) (PEDOT) was electrochemically synthesised in a cholesteric liquid crystal (CLC) electrolyte solution from the terEDOT monomer. PEDOT synthesised from terEDOT was found to enable the formation of a
- Goto, Hiromasa
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- Stable and soluble oligo(3,4-ethylenedioxythiophene)s end-capped with alkyl chains
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The synthesis of a new series of stable and soluble EDOT oligomers end-capped with n-hexyl groups is described. Optical and electrochemical results indicate that the synergy between the direct electron-releasing effects of the ethylenedioxy groups and the self-rigidification resulting from intramolecular interactions controls to a large extent the HOMO-LUMO gap.
- Turbiez, Mathieu,Frere, Pierre,Roncali, Jean
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- Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented Heterocyclic Coupling Reaction
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Prolonged storage (~2 years) or gentle heating (50-80 °C) of crystalline 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) affords a highly conducting, bromine-doped poly(3,4-ethylenedioxythiophene) (PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR spectroscopies. The novel solid-state polymerization (SSP) does not occur for 2,5-dichloro-3,4-ethylenedioxythiophene (DCEDOT), and requires a much higher temperature (>130 °C) for 2,5-diiodo-3,4-ethylenedioxythiophene (DIEDOT). X-ray structural analysis of the above dihalothiophenes reveals short Hal...Hal distances between adjacent molecules in DBEDOT and DIEDOT, but not in DCEDOT. The polymerization may also occur in the melt but is significantly slower and leads to poorly conductive material. Detailed studies of the reaction were performed using ESR, DSC, microscopy, and gravimetric analyses. SSP starts on crystal defect sites; it is exothermic by 14 kcal/mol and requires activation energy of ~26 kcal/mol (for DBEDOT). The temperature dependence of the conductivity of SSP-PEDOT (σrt = 20-80 S/cm) reveals a slight thermal activation. It can be further increased by a factor of 2 by doping with iodine. Using this approach, thin films of PEDOT with conductivity as high as 20 S/cm were fabricated on insulating flexible plastic surfaces.
- Meng, Hong,Perepichka, Dmitrii F.,Bendikov, Michael,Wudl, Fred,Pan, Grant Z.,Yu, Wenjiang,Dong, Wenjian,Brown, Stuart
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- Cyclic thiourea functionalized dyes with binary π-linkers: Influence of different π-conjugation segments on the performance of dye-sensitized solar cells
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A series of cyclic thiourea functionalized dyes containing binary π-linkers were synthesized and applied in the dye-sensitized solar cells. The only difference of these dyes is that one segment of the binary π-linkers is thiophene, n-hexylthiophene, thienothiophene, 3,4-ethylenedioxythiophene, and benzene, respectively. Among them, the dyes incorporating electron-rich thienothiophene or 3,4-ethylenedioxythiophene exhibit the broader absorption bands and higher molar extinction coefficients in the visible region, which can not only enhance the light-harvesting ability but also improve the short-circuit current density; on the other hand, the dyes bearing bulky n-hexylthiophene or 3,4-ethylenedioxythiophene can effectively suppress the intermolecular π-π aggregation and electron recombination owing to larger steric hindrance, which is beneficial to increase the open-circuit voltage.
- Zhu, Shengbo,An, Zhongwei,Chen, Xinbing,Chen, Pei,Liu, Qianfeng
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- Synthesis and electrical properties of novel oligothiophenes partially containing 3,4-ethylenedioxythiophenes
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Five sorts of soluble oligothiophenes (trimer to undecamer) containing 3,4-ethylenedioxythiophene (EDOT) were synthesized, and their optical and electrochemical properties were investigated in relation to the chain length of oligothiophenes and the number of EDOT units. The introduction of the EDOT unit into a main oligothienylene unit induced a red shift of absorption bands and a negative shift of oxidation potentials. The conductivity of an electrochemically oxidized film of undecamer was found to be around 1 S cm-1. A thin-film field effect transistor was preliminary fabricated with neutral undecamer films and the hole mobility was determined.
- Imae, Ichiro,Imabayashi, Saki,Komaguchi, Kenji,Tan, Zhifang,Ooyama, Yousuke,Harima, Yutaka
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- Charge transfer and delocalization in conjugated (ferrocenylethynyl)oligothiophene complexes
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A series of conjugated mono(ferrocenylethynyl)oligothiophene and bis(ferrocenylethynyl)oligothiophene complexes have been prepared. The cyclic voltammograms of the complexes all contain a reversible ferrocene oxidation wave and an irreversible oligothiophene-based wave. The potential difference between the two waves (ΔE) varies from 0.38 to 1.12 V, depending on the length and substitution of the oligothiophene group. Several of the mono(ferrocenylethynyl)oligothiophene complexes couple when oxidized, resulting in the deposition of a redox-active film on the electrode surface. In solution, electrochemical oxidation of the FeII centers yields the corresponding monocations and dications, which exhibit oligothiophene-to-FeIII charge-transfer transitions in the near-IR region. The band maxima of these low-energy transitions correlate linearly with ΔE, while the oscillator strengths show a linear correlation with negative slope with ΔE. The complexes with similar charge-transfer transition dipole lengths show an increase in the extent of charge delocalization with smaller ΔE. Comparisons between complexes with different length oligothiophene ligands show that a reduction in ΔE results either in greater delocalization of charge or in charge being delocalized further along the rigid oligothiophene ligand. These results have important implications in understanding charge delocalization in metal-containing polymers.
- Zhu, Yongbao,Wolf, Michael O.
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- Fully undoped and soluble oligo(3,4-ethylenedioxythiophene)s: Spectroscopic study and electrochemical characterization
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Fully undoped oligo(3,4-ethylenedioxythiophene)s have been synthesized from polycondensation of the corresponding dibromomonomer in the presence of a catalytic Ni(0)-based complex in N,N-dimethylacetamide (DMA). HPLC analysis indicated that the material is constituted of three main oligomers which have also been clearly detected by UV-Visible spectroscopy. Due to its partial solubility in DMA, processability is improved compared to the corresponding insoluble polymer and thin films of oligomers can be deposited by evaporation. Electrochemical and electrochromic properties of undoped film have been carried out. Deep purple in its undoped state, the material becomes sky blue in the oxidized form. The mixture of oligomers was characterized by means of Raman scattering, IR absorption and X-Ray dffraction (XRD), and compared to the poly(3,4-ethylenedioxythiophene) obtained by the oxidative route.
- Tran-Van, Francois,Garreau, Sebastien,Louarn, Guy,Froyer, Gerard,Chevrot, Claude
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- A bromine-catalysis-synthesized poly(3,4-ethylenedioxythiophene)/graphitic carbon nitride electrochemical sensor for heavy metal ion determination
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In this paper, poly(3,4-ethylenedioxythiophene)/graphitic carbon nitride (PEDOT/g-C3N4) composites were prepared by the bromine catalysed polymerization (BCP) method with varying weight ratios of monomer to g-C3N4. For comparison, solid-state polymerization (SSP) and metal oxidative polymerization (MOP) methods were also used for the synthesis of PEDOT/g-C3N4 composites. Electrochemical determination of heavy metal ions (Cd2+ and Pb2+) was carried out by differential pulse voltammetry (DPV) on composite-modified glass carbon electrodes (GCEs), which were prepared by different methods. The obtained composites were analysed by Fourier transform infrared spectroscopy (FT-IR), ultraviolet-visible absorption spectroscopy (UV-vis), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The results showed that the bromine catalysed polymerization (BCP) method is an effective way to prepare the PEDOT/g-C3N4 composite, and the combination of PEDOT with g-C3N4 can improve the electrochemical activity of electrode materials. And, the composite from the BCP method modified electrode (PEDOT/10 wt% g-C3N4/GCE) exhibited the widest linear responses for Cd2+ and Pb2+, ranging from 0.06-12 μM and 0.04-11.6 μM with detection limits (S/N = 3) of 0.0014 μM and 0.00421 μM, respectively.
- Wu, Wei,Ali, Ahmat,Jamal, Ruxangul,Abdulla, Mihray,Bakri, Tursunnisahan,Abdiryim, Tursun
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- Direct C-H Arylation Polymerization to form Anionic Water-Soluble Poly(3,4-ethylenedioxythiophenes) with Higher Yields and Molecular Weights
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A facile and environmentally benign Pd-catalyzed direct C-H arylation polymerization (DAP) has been developed for the syntheses of homo- and copolymers of anionic-group-functionalized 3,4-ethylenedioxythiophenes with high yields (up to 99%), high molecular weights, and narrow polydispersities. The effects of various Pd catalysts, phosphine ligands, and additives on the properties of the polymers have been examined. The method gives anionic poly(3,4-ethylenedioxythiophenes) with higher molecular weights than those produced by the previously reported chemical or electrochemical methods. The method was also used to synthesize polymers functionalized with carboxylic acid groups without the need for protection/deprotection steps. The resulting polymers can be processed from water or highly polar organic solvents. We also demonstrated a phosphine-free, water-mediated, Pd-catalyzed DAP. The anionic poly(3,4-ethylenedioxythiophenes) were stable in water, and are promising for applications in sensors, drug delivery, and cell engineering.
- Ayalew, Hailemichael,Wang, Tian-Lin,Wang, Tsai-Hui,Hsu, Hsiu-Fu,Yu, Hsiao-Hua
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- A planar dithiafulvene based sensitizer forming J-aggregates on TiO2 photoanode to enhance the performance of dye-sensitized solar cells
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A newly planar dithiafulvene sensitizer (DTF-C4) trending to form J-aggregates on the surface of mesoporous TiO2 by simply rinsing with a poor solvent acetonitrile was synthesized. We further show that the self-assembled J-aggregates optimized the TiO2 surface utilization, enhanced the light harvesting ability by broadening and red-shifting the absorption, and suppressed the electron recombination, thereby significantly promoting the solar cell efficiency. Compared to the photoanode surface modified with DTF-C4 and the classical coadsorbent chenodeoxycholic acid (CDCA), the DSC based the DTF-C4 compact J-aggregates exhibited a dramatically improved performance without the loss of adsorbed dyes, uplifting the power conversion efficiency from 4.68% to 7.48% alongside with a high open-circuit voltage of above 850 mV, which is higher than that of the commercial N719-based cell (770 mv).
- Cheng, Jun,Zhang, Fang,Li, Ke,Li, Jie,Lu, Xiaoqing,Zheng, Jingxia,Guo, Kunpeng,Yang, Shihe,Dong, Qingchen
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- Significant Enhancement of the Electrical Conductivity of Conjugated Polymers by Post-Processing Side Chain Removal
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The processability and electronic properties of conjugated polymers (CPs) have become increasingly important due to the potential of these materials in redox and solid-state devices for a broad range of applications. To solubilize CPs, side chains are needed, but such side chains reduce the relative fraction of electroactive material in the film, potentially obstructing π–π intermolecular interactions, localizing charge carriers, and compromising desirable optoelectronic properties. To reduce the deleterious effects of side chains, we demonstrate that post-processing side chain removal, exemplified here via ester hydrolysis, significantly increases the electrical conductivity of chemically doped CP films. Beginning with a model system consisting of an ester functionalized ProDOT copolymerized with a dimethylProDOT, we used a variety of methods to assess the changes in polymer film volume and morphology upon hydrolysis and resulting active material densification. Via a combination of electrochemistry, X-ray photoelectron spectroscopy, and charge transport models, we demonstrate that this increase in electrical conductivity is not due to an increase in degree of doping but an increase in charge carrier density and reduction in carrier localization that occurs due to side chain removal. With this improved understanding of side chain hydrolysis, we then apply this method to high-performance ProDOT-alt-EDOTx copolymers. After hydrolysis, these ProDOT-alt-EDOTx copolymers yield exceptional electrical conductivities (~700 S/cm), outperforming all previously reported oligoether-/glycol-based CP systems. Ultimately, this methodology advances the ability to solution process highly electrically conductive CP films.
- Ponder, James F.,Gregory, Shawn A.,Atassi, Amalie,Menon, Akanksha K.,Lang, Augustus W.,Savagian, Lisa R.,Reynolds, John R.,Yee, Shannon K.
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supporting information
p. 1351 - 1360
(2022/02/09)
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- Solid-state synthesis of conjugated doped poly(3,4-ethylenedioxythiophene): An effective adsorbent for selective anionic dye removal
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In this work, we report the adsorption studies of dyes using as-prepared doped poly(3,4-ethylenedioxythiophene) (PEDOT). The conjugated polymer PEDOT was prepared by the solid-state polymerization method and used as an effective adsorbent for the removal
- Gupta, Sonal,Kumar, Rachana,Mishra, Anamika,Patra, Asit
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- Azatruxene-Based, Dumbbell-Shaped, Donor–π-Bridge–Donor Hole-Transporting Materials for Perovskite Solar Cells
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Three novel donor–π-bridge–donor (D-π-D) hole-transporting materials (HTMs) featuring triazatruxene electron-donating units bridged by different 3,4-ethylenedioxythiophene (EDOT) π-conjugated linkers have been synthesized, characterized, and implemented in mesoporous perovskite solar cells (PSCs). The optoelectronic properties of the new dumbbell-shaped derivatives (DTTXs) are highly influenced by the chemical structure of the EDOT-based linker. Red-shifted absorption and emission and a stronger donor ability were observed in passing from DTTX-1 to DTTX-2 due to the extended π-conjugation. DTTX-3 featured an intramolecular charge transfer between the external triazatruxene units and the azomethine–EDOT central scaffold, resulting in a more pronounced redshift. The three new derivatives have been tested in combination with the state-of-the-art triple-cation perovskite [(FAPbI3)0.87(MAPbBr3)0.13]0.92[CsPbI3]0.08 in standard mesoporous PSCs. Remarkable power conversion efficiencies of 17.48 percent and 18.30 percent were measured for DTTX-1 and DTTX-2, respectively, close to that measured for the benchmarking HTM spiro-OMeTAD (18.92 percent), under 100 mA cm?2 AM 1.5G solar illumination. PSCs with DTTX-3 reached a PCE value of 12.68 percent, which is attributed to the poorer film formation in comparison to DTTX-1 and DTTX-2. These PCE values are in perfect agreement with the conductivity and hole mobility values determined for the new compounds and spiro-OMeTAD. Steady-state photoluminescence further confirmed the potential of DTTX-1 and DTTX-2 for hole-transport applications as an alternative to spiro-OMeTAD.
- Illicachi, Luis A.,Urieta-Mora, Javier,Calbo, Joaquín,Aragó, Juan,Igci, Cansu,García-Benito, Inés,Momblona, Cristina,Insuasty, Braulio,Ortiz, Alejandro,Roldán-Carmona, Cristina,Molina-Ontoria, Agustín,Ortí, Enrique,Martín, Nazario,Nazeeruddin, Mohammad Khaja
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supporting information
p. 11039 - 11047
(2020/08/03)
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- Approaching the Integer-Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross-Coupling
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A library of symmetrical linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach compared to the existing methods. The modularity of this approach is demonstrated with the preparation of discreet oligothiophenes with up to 10 thiophene repeat units. Symmetrical oligothiophenes are prototypical organic semiconductors where their molecular electrical doping as a function of the chain length can be assessed spectroscopically. An oligothiophene critical length for integer charge transfer was observed to be 10 thiophene units, highlighting the potential use of discrete oligothiophenes as doped conduction or injection layers in organic electronics applications.
- Forgione, Pat,Hase, Hannes,Liu, Jiang Tian,Salzmann, Ingo,Taylor, Sarah
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supporting information
p. 7146 - 7153
(2020/03/23)
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- Electrochromic compound and application thereof, electrochromic device manufactured by using electrochromic compound and application of electrochromic device
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The invention provides an electrochromic compound and application thereof, an electrochromic device manufactured by using the electrochromic compound and application of the electrochromic device. According to the electrochromic compound, the conjugated st
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Paragraph 0064; 0065; 0066; 0072
(2019/01/06)
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- Radical-Cascade Avenue for 3,4-Fused-Ring-Substituted Thiophenes
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A single-step intramolecular radical cascade reaction of diynes and thioacetic acid in the presence of a catalytic amount of azobis(isobutyronitrile) as a radical initiator has been developed to synthesize thiophenes. This method allows easy and effective construction of a thiophene scaffold having 3,4-fused-ring substitution and unsubstituted 2,5-positions for further functionalization and polymerization. Using this method, derivatives of cyclopenta[c]thiophene, 3,4-ethylenedioxythiophene, and thiophene-containing spirocyclic compound have been synthesized.
- Agrawal, Abhijeet R.,Kumar, Neha Rani,Debnath, Sashi,Das, Sarasija,Kumar, Chandan,Zade, Sanjio S.
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supporting information
p. 4728 - 4731
(2018/08/23)
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- Tuning the painter's palette: Subtle steric effects on spectra and colour in conjugated electrochromic polymers
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A series of vibrantly coloured π-conjugated electrochromic polymers (ECPs) were designed and synthesized with the goal of extracting structure-property relationships from subtle changes in steric strain or relaxation. These are soluble all donor, electron rich, alternating polymers based on repeat units of 3,4-ethylenedioxythiophene (EDOT), 3,4-propylenedioxythiophene (ProDOT), and an acyclic dioxythiophene (AcDOT) in varying combinations to tune steric interactions and the subsequent optical absorption for fine colour control. Two families of polymers were formed where ProDOT2-EDOT, ProDOT-EDOT, and ProDOT2-EDOT2 constitute new shades of blues while AcDOT2-ProDOT, AcDOT-ProDOT, and AcDOT-EDOT yield new hues of magentas with the homopolymers of ProDOT and AcDOT and the copolymer AcDOT2-EDOT2 serving as comparisons. The polymers were synthesized using direct (hetero)arylation polymerization. Examinations of the optoelectronic properties via cyclic voltammetry, spectroelectrochemistry, and colorimetry show that by subtly varying the level of steric relaxation or strain in the form of EDOT or AcDOT content, lower or higher energy absorption transitions are produced respectively. This increase in relaxation or strain allows more short or long wavelength light to transmit, giving new shades of blues or magentas respectively. Since these are all donating polymers, they exhibit changes in contrast no less than 70% at the λmax with the exception of AcDOT-EDOT. The most desirable electrochromic properties were achieved with ProDOT2-EDOT2 and AcDOT2-ProDOT, with band gaps (Eg) and neutral state Lab colour values (-a and +a correspond to green and red and -b and +b correspond to blue and yellow respectively and L represents the lightness) of 1.74 eV, 37, 12, -63 and 2.01 eV, 56, 59, -16 respectively. The highly transmissive oxidized state colour values for ProDOT2-EDOT2 and AcDOT2-ProDOT are 92, -3, -3 and 91, -2, -1 respectively. These structure-property relationships grant a greater ability to tune light absorption across the visible, with colour properties similar to ECPs made through other methods without using donor-acceptor effects. This all donor steric tuning method leads to considerably higher levels of transparency when the polymers are fully oxidized.
- Kerszulis,Johnson,Kuepfert,Khoshabo,Dyer,Reynolds
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supporting information
p. 3211 - 3218
(2015/03/31)
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- HOLE TRANSPORTING MOLECULES AND THEIR USE IN SOLAR CELLS
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The invention relates to hole transporting molecules for use in solar cells. In particular, present invention relates to such hole transporting molecules comprising thiophene or bithiophene cores.
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Paragraph 0125; 0133; 0135
(2015/06/18)
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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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- A simple 3,4-ethylenedioxythiophene based hole-transporting material for perovskite solar cells
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We report a novel electron-rich molecule based on 3,4- ethylenedioxythiophene (H101). When used as the hole-transporting layer in a perovskite-based solar cell, the power-conversion efficiency reached 13.8 % under AM 1.5G solar simulation. This result is comparable with that obtained using the well-known hole transporting material 2,2′,7,7′- tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (spiro-OMeTAD). This is the first heterocycle-containing material achieving >10 % efficiency in such devices, and has great potential to replace the expensive spiro-OMeTAD given its much simpler and cheaper synthesis. Heterocycle power! A power-conversion efficiency of 13.8 % under AM 1.5G illumination was achieved in a perovskite-based solar cell with a new hole-transporting material based on 3,4-ethylenedioxythiophene (H101). This is the first heterocycle-containing material with >10 % efficiency in such devices, and has great potential to replace the more expensive spiro-OMeTAD, given its much simpler and less expensive synthesis.
- Li, Hairong,Fu, Kunwu,Hagfeldt, Anders,Graetzel, Michael,Mhaisalkar, Subodh G.,Grimsdale, Andrew C.
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supporting information
p. 4085 - 4088
(2014/05/06)
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- Synthesis of triphenylamine copolymers and effect of their chemical structures on physical properties
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A series of charge transporting triphenylamine (TPA) polymers containing 2,1,3-benzothiadiazole (BTH) and/or 3,4-ethylenedioxythiophene (EDOT) unit(s) in the backbone were synthesized via C-N coupling polymerization using a palladium catalyst system. The
- Tsuchiya, Kousuke,Sakakura, Takashi,Ogino, Kenji
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scheme or table
p. 5200 - 5208
(2012/04/17)
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- The first direct experimental comparison between the hugely contrasting properties of PEDOT and the all-sulfur analogue PEDTT by analogy with well-defined EDTT-EDOT copolymers
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The structures of poly(3,4-ethylenedioxythiophene) (PEDOT) and poly(3,4-ethylenedithiathiophene) (PEDTT) vary only in the substituent chalcogen atoms, yet the electronic properties of the materials are surprisingly dissimilar. The difference in electronic band gaps is approximately 0.8 eV and the polymers behave very differently upon p-doping. Two new terthiophenes have been synthesised using Negishi coupling methods. The X-ray crystal structures of EDOT-EDTT-EDOT (OSO) and EDTT-EDOT-EDTT (SOS) show strong intramolecular chalcogen-chalcogen contacts which are responsible for persistent conformers in solution and solid state, although significant interchain interactions should also influence the properties of the materials. SOS and OSO can be polymerised by electrochemical oxidation to give the corresponding, well-defined poly(terthiophenes) PSOS and POSO. Spectroelectrochemical studies on all four polymers reveal strong similarities between PEDTT and PSOS, and between PEDOT and POSO. Together with independent electrochemical and absorption studies, the results indicate that the unique properties of PEDOT are influenced more by conformational effects (intrachain S...O contacts) than substituent effects. The Royal Society of Chemistry 2005.
- Spencer, Howard J.,Skabara, Peter J.,Giles, Mark,McCulloch, Iain,Coles, Simon J.,Hursthouse, Michael B.
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p. 4783 - 4792
(2007/10/03)
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- Copolymers of 3,4-ethylenedioxythiophene and of pyridine alternated with fluorene or phenylene units: Synthesis, optical properties, and devices
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We report the synthesis of four conjugated copolymers based on alkylated fluorene or phenylene units which band gap is tuned by the regular insertion of an electron-donating or electron-withdrawing unit, (3,4-ethylenedioxy)thiophene and pyridine, respecti
- Aubert, Pierre-Henri,Knipper, Martin,Groenendaal, Lambertus,Lutsen, Laurence,Manca, Jean,Vanderzande, Dirk
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p. 4087 - 4098
(2007/10/03)
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- Optical and redox properties of a series of 3,4-ethylenedioxythiophene oligomers
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The optical and redox properties of a series of 3,4-ethylenedioxythiophene oligomers (EDOTn, n=1-4) and their β,β'-unsubstituted analogues (Tn, n=1-4) are described. Both series are end capped with phenyl groups to prevent irreversible a-coupling reaction
- Apperloo, Joke J.,Bert Groenendaal,Verheyen, Hilde,Jayakannan, Manickam,Janssen, Rene A. J.,Dkhissi, Ahmed,Beljonne, David,Lazzaroni, Roberto,Bredas, Jean-Luc
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p. 2384 - 2396
(2007/10/03)
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- Synthesis and electronic structure investigations of α,ω-bis(arylthio)oligothiophenes: Toward understanding wire-linker interactions in molecular-scale electronic materials
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Several oligothiophenes with 2-mesitylthio (MesS) substituents have been prepared and studied by UV-visible spectroscopy and cyclic voltammetry. These compounds can be considered as models for thiol-terminated conjugated oligomers, which have attracted in
- Hicks, Robin G.,Nodwell, Matthew B.
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p. 6746 - 6753
(2007/10/03)
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