Novel organic dyes with anchoring group of barbituric/thiobarbituric acid and their application in dye-sensitized solar cells

Hosseinzadeh, Behzad; Beni, Alireza Salimi; Chermahini, Alireza Najafi; Ghahary, Raheleh; Teimouri, Abbas

doi:10.1016/j.synthmet.2015.06.018

Cited by 39 publications

(20 citation statements)

References 47 publications

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“…At this stage, we turned our attention to the synthesis of thioamide 1‐SN , since we also wanted to investigate its use as a potential sensitizer for DSSCs, in analogy with some literature reports describing the possibility to anchor organic dyes to TiO 2 by means of a thioamide‐like moiety (usually inserted within a heterocyclic structure) . Accordingly, we first converted acid DF15 to the corresponding amide 7 by means of sequential reactions with oxalyl chloride and gaseous ammonia, and then reacted the latter with LR under mild conditions to obtain the desired product in good overall yield (Scheme , top).…”

Section: Resultsmentioning

confidence: 99%

“…0.1 %, Figure S7). From this observation, it seems that the thioamide group per se is not adequate to ensure a proper adsorption of the dye on the semiconductor layer, suggesting that sensitizer binding should take place through a different functional group also in the above‐mentioned cases of “thioamide‐like” fragments embedded in more complex heterocyclic anchoring moieties (thiobarbituric acid, 2‐aminothiazol‐4‐one) …”

Section: Resultsmentioning

confidence: 99%

“…As detailed below, while the synthesis of thiocarboxylic acid 1‐SO proceeded smoothly, isolation of dithiocarboxylic acid 1‐S 2 was not successful due to its insufficient stability: nevertheless, the relative spectroscopic properties could be assessed and compared to those of DF15 by scrutinizing the corresponding benzylic esters (Figure ). We also prepared thioamide 1‐SN to investigate the capability of such functional group to bind TiO 2 , in analogy with the above‐mentioned reports . Spectroscopic characterization of the new dyes was complemented by transient absorption spectroscopy (TAS) measurements, which allowed us to evaluate the kinetics of photoexcitation and electron injection into the semiconductor.…”

Section: Introductionmentioning

confidence: 97%

“…Chauhan and co‐workers reported the application of ferrocenyl‐containing compounds bearing a dithiocarbamate coordinating group and the corresponding complexes with various metals (including Zn, Cd, Hg, Cu, Pd, Pt, Co) as sensitizers or co‐sensitizers in DSSCs, recording efficiencies close to those obtained with reference dye N719 under the same conditions . A few groups independently explored the possibility to use thiobarbituric acid as an anchoring group and compared the performances of the corresponding dyes with those of their oxygenated analogues: monodentate dyes based on simple phenyl or carbazole backbones,, or dyes with two anchoring groups on the same molecular structure were investigated. Regardless of structural modifications, computational studies and IR spectroscopic analyses indicated that the thioamide group seemed to be involved in bonding to the semiconductor, but efficiencies remained quite low (well below 1 %).…”

Section: Introductionmentioning

confidence: 99%

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Tailoring the Optical Properties of Organic D‐π‐A Photosensitizers: Effect of Sulfur Introduction in the Acceptor Group

et al. 2018

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In this work, we present for the first time the synthesis and characterization of potential DSSC organic sensitizers whose cyanoacrylic acceptor/anchoring group was modified by replacement of oxygen with one or more sulfur atoms. Using known carboxylic acid dye DF15 as a reference, their TD‐DFT computational analysis indicated that oxygen‐sulfur substitution should induce a significant red‐shift of the corresponding UV/Vis absorption spectra. Whereas synthesis of monothiocarboxylic derivatives of DF15 was successfully carried out, isolation of the analogous dithiocarboxylic acid proved impossible due to its very low stability: despite that, their relative spectroscopic properties could be compared by analyzing the corresponding benzylic esters. Combined computational and transient absorption spectroscopy studies suggested that photoexcited thiocarboxylic acid 1‐SO and thioamide 1‐SN were able to inject electrons into nanocrystalline TiO2 and indicated a similar charge injection efficiency for 1‐SO relative to DF15. Preliminary DSSC studies showed that, when tert‐butylpyridine was present in the electrolyte solution, 1‐SO was rapidly degraded; however, in the absence of basic additives 1‐SO provided a sufficiently stable device, giving a slightly lower efficiency compared to carboxylic sensitizer DF15.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Tailoring the Optical Properties of Organic D‐π‐A Photosensitizers: Effect of Sulfur Introduction in the Acceptor Group

et al. 2018

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“…[1][2][3] Electron-deficient groups, such as rhodanine (RH), 4,5 1,3-indandione (IN), 6,7 and 1,1-dicyanomethylene-3-indanone (CNIN) 8,9 have been widely used as acceptor units, together with fused-ring-based electron-rich groups, such as carbazole (Cz), 10,11 fluorene (Flu), 12,13 indacenodithiophene (IDT), 14,15 and indacenodithienothiophene (IDTT). 19 In 2017, our group reported the synthesis of Cz-BAR and Flu-BAR, in which electron-rich Cz and Flu cores were end-capped with electron-deficient BAR groups, providing a PCE of 1.57% when combined with poly(3-hexylthiophene) in solution. Sullivan et al reported the use of a BAR-containing electron acceptor to evaporate bilayer OPV devices, in which a PCE of 2.6% was achieved using an inverted configuration and SubPc as the donor.…”

Section: Introductionmentioning

confidence: 99%

Non‐Fullerene Small Molecule Acceptors Containing Barbituric Acid End Groups for Use in High‐performance OPVs

Choe

Lee

Lim

2018

Bulletin Korean Chem Soc

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We synthesized two new bithiophene-based small molecules, TT-BBAR, and TT-OBAR, having butyland octyl-substituted barbituric acid (BAR) groups, respectively, via a well-known synthetic method, the Knoevenagel condensation, in high yield. These small molecules displayed solubilities and thermal stabilities sufficient for the fabricating organic photovoltaic cells (OPVs) and were designed to have relatively low molecular orbital energy levels and act as non-fullerene acceptors (NFAs) for use in OPVs upon introduction of electron-withdrawing BAR groups at both ends. For example, the LUMO and HOMO energy levels of TT-OBAR were −3.79 and of −5.84 eV, respectively, clearly lower than those of a polymer donor, PTB7-Th. Importantly, the small molecules featured an energy offset with PTB7-Th sufficient for achieving exciton dissociation. The optical and electrochemical properties of TT-BBAR and TT-OBAR did not depend on the alkyl chain length. Finally, OPV devices were fabricated in an inverted structure using a solvent process. The power conversion efficiency of TT-OBAR (1.34%) was found to be slightly higher than that of TT-BBAR (1.16%). The better performance and higher short-circuit current value of TT-OBAR could be explained based on a morphological AFM study, in which TT-OBAR displayed a more homogeneous morphology with a root-mean-square value of 1.18 nm compared to the morphology of TT-BBAR (11.7 nm) induced by increased alkyl chain length.

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Ag(I), In (III), and Sn (II) chelates of azo mesalamine drug: Characterization, DFT studies, molecular docking and biological evaluation

Elaziz

Gaber

El-Wakiel

et al. 2022

Applied Organom Chemis

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A new set of Ag(I), In (III) and Sn (II) chelates based on azo dye ligand of 5-aminosalicylic acid (H 2 L) were prepared. The structures of this novel chelates have already been confirmed by elemental analysis, thermogravimetric analysis, molar conductance, X-ray diffraction (XRD), UV-Vis, Fourier-transform infrared spectroscopy (FT-IR), and mass spectra. The lower conductivity values showed the non-electrolytic nature. The kinetic and thermodynamic parameters were determined through using Coats-Redfern model, also, potential application; the antibacterial activity of the target compounds was tested by examining their effect on the development of various strains of bacteria. Utilizing UV-visible absorption measurements, we investigated the interaction between calf thymus DNA and the evaluated compounds. According to the findings, the intercalative binding approach, the chelates interact with DNA by assessing the binding constants. Additionally, the in vitro antimicrobial properties of the ligand and its metal chelates were evaluated. The theoretical density functional theory (DFT) simulations for the azo dye ligand (H 2 L) were completed by using B3LYP/6-311G ++ (d,p) basis functions, and the B3LYP/LanL2DZ for Ag(I), In (III), and Sn (II) chelatesshows that the uninuclear Ag(I) and Sn(II) chelates under consideration have a tetrahedral geometry. Although the experimental data are in agreement with the octahedral shape for binuclear In (III) chelate. Molecular docking simulations were carried out using molecular operating environment (MOE) software for the ligand and its chelates. Docking simulation results indicated that the Ag(I) chelate was more potent and exhibited a higher affinity for the (3QKK) protein than the In (III) and Sn (II) chelates. This is in agreements with the biological evaluations under studies.

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Novel organic dyes with anchoring group of barbituric/thiobarbituric acid and their application in dye-sensitized solar cells

Cited by 39 publications

References 47 publications

Tailoring the Optical Properties of Organic D‐π‐A Photosensitizers: Effect of Sulfur Introduction in the Acceptor Group

Tailoring the Optical Properties of Organic D‐π‐A Photosensitizers: Effect of Sulfur Introduction in the Acceptor Group

Non‐Fullerene Small Molecule Acceptors Containing Barbituric Acid End Groups for Use in High‐performance OPVs

Ag(I), In (III), and Sn (II) chelates of azo mesalamine drug: Characterization, DFT studies, molecular docking and biological evaluation

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