- A new series of EDOT based co-sensitizers for enhanced efficiency of cocktail DSSC: A comparative study of two different anchoring groups
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Herein, we report the design and synthesis strategy of a new class of five EDOT based co-sensitizers (CSGR1-5) by introducing different donors (2,3,4-trimethoxypheny, 2,4-dibutoxyphenyl, and 2,4-difluorophenyl) and anchoring groups (rhodamine-3-acetic acid and cyanoacetic acid) systematically. The synthesized metal-free organic co-sensitizers were employed for cocktail dye-sensitized solar cells along with N749 (black dye). The DSSC devices with a mixture of co-sensitizers (CSGR1-5) and N749 have shown a 7.95%, 8.40%, 7.81%, 6.56% and 6.99% power conversion efficiency (PCE) respectively, which was more than that of single N749 dye PCE (6.18%). Enhanced efficiency could be ascribed to the increased short circuit current (Jsc) and open circuit voltage (Voc). The increased Jsc was achieved due to enhanced light harvesting nature of N749 device upon co-sensitization with CSGR dyes and feasible energy levels of both the dyes. The Voc was improved due to better surface coverage which helps in decreasing the rate of recombination. The detailed optical and electrochemical properties were investigated and complimented with theoretical studies (DFT).
- Koyyada, Ganesh,Chitumalla, Ramesh Kumar,Thogiti, Suresh,Kim, Jae Hong,Jang, Joonkyung,Chandrasekharam, Malapaka,Jung, Jae Hak
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- Synthesis and Optical Properties of New Chalcones Containing a 3,4-Ethylenedioxythiophene Fragment
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Abstract: A new series of chalcones bearing two or more 3,4-ethylenedioxythiophene fragments were synthesized, and their optical properties were studied. The Stokes shifts (Δλ) and band gaps (Egopt) were calculated on the basis of the absorption and emission spectra. The largest Stokes shift (115 nm) was found for a symmetrical product of the terephthalaldehyde and 3,4-ethylenedioxythiophene-2-carbaldehyde condensation, and the smallest band gap (1.93 eV) is characteristic of a chalcone that contains a 2,2',5',2''-ter(3,4-ethylenedioxythiophene). Correlations were established between the band gap and mutual arrangement of the 3,4-ethylenedioxythiophene fragments in the prepared chalcones.
- Ignashevich,Shavrina,Shklyaeva,Abashev
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p. 1920 - 1928
(2021/01/13)
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- Divergent Synthesis and Evaluation of the in vitro Cytotoxicity Profiles of 3,4-Ethylenedioxythiophenyl-2-propen-1-one Analogues
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A new series of 3,4-ethylenedioxythiophene (EDOT)-appended propenones were prepared by condensation reaction and their in vitro cytotoxicity effects were evaluated against five human cancer cell lines. Preliminary structure–activity relationships of EDOT-
- Karunakaran, Jayachandran,Dhatchana Moorthy, Nachiappan,Chowdhury, Somenath Roy,Iqbal, Saleem,Majumder, Hemanta K.,Gunasekaran, Krishnasamy,Vellaichamy, Elangovan,Mohanakrishnan, Arasambattu K.
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p. 1418 - 1430
(2019/08/07)
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- Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies
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Six new conjugated polymers comprising of carbazole, fluorene, and ethylene dioxythiophene (EDOT) moieties along the backbone with a pendant cyano group attached to the ethylene moiety have been designed and synthesized via Sonogashira coupling polymerization reaction. Optical and electrochemical characterizations have shown that the energy band gaps lie within the range of 2.35–2.44 eV. Additionally, the presence of carbazole and EDOT makes these polymers better hole transporting materials, which is reflected from their low oxidation potential peaks (0.55–1.11 V) in cyclic voltammograms. Furthermore, the aggregation enhanced emission (AEE) phenomenon resulted in a 2.6-fold increase in fluorescence intensity in a 90:10 THF/water mixture in comparison to pristine THF. The AEE properties were further verified by DLS (dynamic light scattering) experiment and SEM (scanning electron microscopy) studies. Polymers in solution as well as in polystyrene matrix emit in the green region (quantum yield in solution state Φf =41–43%) with CIE values (0.25–0.36, 0.52–0.57). Excellent thermal stability is observed for the new polymers.
- Anand, Vivek,Ramachandran, Elumalai,Dhamodharan, Raghavachari
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p. 2774 - 2784
(2016/07/28)
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- D-π-A structured porphyrins for efficient dye-sensitized solar cells
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In this study, new push-pull alkoxy-wrapped zinc porphyrin dyes with intramolecular donor-π-acceptor structures have been designed and synthesized for dye-sensitized solar cells (DSCs). The linkers based on thiophene or 2,3-dihydrothieno[3,4-b][1,4] dioxine with cyanoacetic acid can broaden the spectral response of porphyrins into the near-IR region (~850 nm), which is mainly attributed to the cyanoacetic acid group. However, porphyrins with cyanoacrylic acid as an anchoring group lead to a faster charge recombination rate at the dye-sensitized heterojunction interface, which lowers the device photovoltaic performance. By using porphyrins with a rigid π-linker feature structure that is 5-ethynylthiophene-2-carboxylic acid, highly efficient DSC devices with a power conversion efficiency of 9.5% can be obtained. Spectral, electrochemical, photovoltage transient decay and impedance measurements are performed to reveal the influence of π-conjugated linkers and anchoring groups upon the optoelectronic features of porphyrin dyes in DSCs.
- Lu, Jianfeng,Xu, Xiaobao,Cao, Kun,Cui, Jin,Zhang, Yibo,Shen, Yan,Shi, Xiaobo,Liao, Liangsheng,Cheng, Yibing,Wang, Mingkui
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supporting information
p. 10008 - 10015
(2013/09/02)
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- Synthesis of π-conjugated 2,2:6′,2″-terpyridine-substituted oligomers based on 3,4-ethylenedioxythiophene
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Dissymmetric π-conjugated monomers and oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units and bearing terpyridine end groups were synthesized in good yields through Vilsmeyer-Haak formylation followed by a reaction with 2-acetylpyridine in ba
- Fillaud, Laure,Trippé-Allard, Ga?lle,Lacroix, Jean Christophe
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p. 1028 - 1031
(2013/04/23)
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- Chemistry of polyhalogenated nitrobutadienes, part 11: Ipso-formylation of 2-chlorothiophenes under Vilsmeier-Haack conditions
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The regioselective ipso-formylation of electron-rich, 3,4-push-pull- substituted 2-chlorothiophenes under Vilsmeier-Haack conditions was performed in good yields. The synthetic scope of this new reaction was explored using various halothiophenes, chloroanilines, and 1-methyl-3-chloroindole. In comparison with their structural C-H analogs the chlorinated thiophenes, anilines, and the indole proved to be less reactive toward electrophilic attack by chloromethyleniminium salts.
- Vogt, Eva-Janina,Zapol'skii, Viktor A.,Nutz, Eva,Kaufmann, Dieter E.
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p. 285 - 294
(2012/07/14)
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- Simple organic molecules bearing a 3,4-ethylenedioxythiophene linker for efficient dye-sensitized solar cells
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3,4-Ethylenedioxythiophene and bis[2-(2-methoxyethoxy)ethoxy]thiophene bridged donor-acceptor molecules for dye-sensitized solar cells have been synthesized, one of which achieved a solar-to-energy conversion efficiency of 7.3%, compared to 7.7% optimized for N719 dye. The Royal Society of Chemistry.
- Liu, Wei-Hsin,Wu, I-Che,Lai, Chin-Hung,Lai, Cheng-Hsuan,Chou, Pi-Tai,Li, Yi-Tsung,Chen, Chao-Ling,Hsu, Yu-Yen,Chi, Yun
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supporting information; experimental part
p. 5152 - 5154
(2009/03/11)
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- Thiophene backbone amide linkers, a new class of easily prepared and highly acid-labile linkers for solid-phase synthesis
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Solid-phase synthesis is of tremendous importance for small-molecule and biopolymer synthesis. Linkers (handles) that release amide-containing products after completion of solid-phase synthesis are widely used. Here we present a new class of highly acid-labile backbone amide linkers (BAL handles) based on 3,4-ethylenedioxythiophene (EDOT), which we have termed T-BAL. These thiophene linkers are synthesized in three convenient steps from commercially available EDOT. In the linker design, the spacer was introduced to the EDOT core either via a carbon-carbon bond or via a thioether linkage. Introduction of the spacer via a C-C bond was performed by a chemoselective Negishi coupling without transient protection of the aldehyde group to provide the T-BAL1 handle. Introduction via a thioether linkage was performed by a facile nucleophilic aromatic substitution between the brominated EDOT aldehyde and unprotected mercapto acids to provide T-BAL2 and T-BAL3 handles. The minimal use of protecting groups gave the corresponding linker molecules in few synthetic steps and in good yields. After anchoring of the linker to a polymeric support, introduction of the first amino acid was achieved by reductive amination, giving a secondary amine. A following acylation of the secondary amine with a symmetrical amino acid anhydride resulted in a backbone amide linkage between the handle and the growing substrate (e.g., peptide chain). After solid-phase synthesis, the substrates could be released from the resin by either low acid conditions using 1% TFA in CH2Cl2 or high acid conditions such as 50% TFA in CH2Cl2. Peptide thioesters could be released from the T-BAL1 handle under very mild conditions using aqueous acetic acid. Tert-butyl based protecting groups, tert-butyl esters, tert-butyl ethers, and Boc groups, as well as dimethyl acetals were relatively stable to these mild conditions for release of the peptides.
- Jessing, Mikkel,Brandt, Malene,Jensen, Knud J.,Christensen, Jorn B.,Boas, Ulrik
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p. 6734 - 6741
(2007/10/03)
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- Controlling stereochemical outcomes of asymmetric processes by catalyst remote molecular functionalizations: Chiral diamino-oligothiophenes (DATs) as ligands in asymmetric catalysis
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The synthesis, characterization, and structure-guided application of a new class of highly versatile chiral C2-symmetric diamine-oligothiophene ligands in Pd-catalyzed asymmetric transformations are presented. Experimental investigations of the
- Albano, Vincenzo Giulio,Bandini, Marco,Barbarella, Giovanna,Melucci, Manuela,Monari, Magda,Piccinelli, Fabio,Tommasi, Simona,Umani-Ronchi, Achille
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p. 667 - 675
(2007/10/03)
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- Preparative fluorous mixture synthesis of diazonium-functionalized oligo(phenylene vinylene)s
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(Chemical Equation Presented) A series of building blocks for the synthesis of oligo(phenylene vinylene)s (OPVs) and hybrid oligomers were prepared, and alternating Heck coupling and Horner-Wadswoth-Emmons (HWE) reactions were used to couple the building blocks. Model studies were carried out to optimize the reaction strategies. The products were made to bear aryl diazonium functionalities that allow them to be used as surface grafting moieties in hybrid silicon/molecule assemblies. A library of OPV and hybrid oligomer tetramers was synthesized using fluorous mixture synthesis (FMS). The fluorous tags, which are secondary amines bearing different numbers of fluorine atoms, were synthesized and used as phase tags in mixture synthesis. The tags and substrates were anchored together by triazene linkages. The mixture synthesis was monitored by analytical HPLC on a fluorous column, and isolation of final OPV and hybrid oligomer tetramers was achieved by preparative HPLC. At the end of the FMS, after demixing, the tagged products were detagged by cleaving the triazene linkage and generating a series of aryl diazonium compounds. The fluorous tags could be recovered and reused. The NMR spectra of the 1-aryl-3,3-dialkyltriazenes are discussed.
- Jian, Huahua,Tour, James M.
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p. 3396 - 3424
(2007/10/03)
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