Organic Chromophores Based on a Fused Bis‐Thiazole Core and Their Application in Dye‐Sensitized Solar Cells

Dessì, Alessio; Consiglio, Gabriella Barozzino; Calamante, Massimo; Reginato, Gianna; Mordini, Alessandro; Peruzzini, Maurizio; Taddei, Maurizio; Sinicropi, Adalgisa; Parisi, Maria Laura; Biani, Fabrizia Fabrizi de; Basosi, Riccardo; Mori, R.; Spatola, Michele; Bruzzi, M.; Zani, Lorenzo

doi:10.1002/ejoc.201301094

Cited by 6 publications

(6 citation statements)

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“…Considering that the Pechmann core proved to be quite sensitive to the presence of excess acetic acid, we needed to modify the standard reaction conditions, which commonly require using a mixture of toluene and acetic acid as the solvent and a large excess of cyanoacetic acid and ammonium acetate. 30 Instead, we decided to use a stoichiometric amount of piperidine 25 as the base and a mixture of toluene and acetonitrile as the solvent. In this way, provided that the reaction is stopped before the complete conversion of the starting materials to minimize degradation, we have been able to recover the desired dyes 1 and 2 in 37 and 62% isolated yield, respectively (Scheme 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

New Blue Donor–Acceptor Pechmann Dyes: Synthesis, Spectroscopic, Electrochemical, and Computational Studies

et al. 2019

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The design, synthesis, and characterization of a new class of blue-colored thiophene-substituted Pechmann dyes are reported. Due to a distinguishing blue coloration and the capability to absorb light in one of the most photon-dense regions of the solar spectrum, such compounds are of great interest for application as photoactive materials in organic optoelectronics, in particular, in dye-sensitized solar cells. To achieve fine tuning of the optical and electrochemical properties, the electron-poor thiophene-bis-lactone moiety has been decorated with donor (D) and acceptor groups (A), targeting fully conjugated D–A−π–A structures. The designed structures have been investigated by means of DFT and time-dependent DFT calculations, and the most promising dyes have been synthesized. These molecules represent the very first preparation of unsymmetrical Pechmann derivatives. Optical and electrochemical properties of the new dyes have been studied by cyclic voltammetry and UV–vis and fluorescence spectroscopy. In two cases, test cells were built proving that a photocurrent can indeed be generated when using electrolytes especially formulated for narrow-band-gap dyes, although with a very low efficiency.

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Section: ■ Results and Discussionmentioning

confidence: 99%

New Blue Donor–Acceptor Pechmann Dyes: Synthesis, Spectroscopic, Electrochemical, and Computational Studies

et al. 2019

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“…We are getting the optical properties of all sensitized compounds in chloroform solution [61,62]. The chloroform has been used in UV-Visible absorption spectrum as solvent on quinoxaline based dyes [13,31]. Since the function used is very economical and requires only one calculation, we took into account for the simulated spectra 20 excited states to obtain a better spectrum for the molecules studied here.…”

Section: Optical Propertiesmentioning

confidence: 99%

“…On the other hand, with the experimental results obtained for organic compounds without metals, research is again restricted. Just some study groups have searched the photophysical and optoelectronic properties for dye sensitizers [28,29], as well intra compound e À -dynamic process enter compound and TiO 2 [30,31]. So, the investigation study of novel quinoxaline-based dyes was signalized in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigation using DFT of quinoxaline derivatives for electronic and photovoltaic effects

Assyry

Lamsayah

Warad

et al. 2020

Heliyon

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Photovoltaic properties of solar cells based on fifteen organic dyes have been studied in this work. B3LYP/6-311G (d,p) methods are realized to obtain geometries and optimize the electronic properties, optical and photovoltaic parameters for some quinoxaline derivatives. The results showed that time dependent DFT investigations using the CAM-B3LYP method with the polarized split-valence 6-311G (d,p) basis sets and the polarizable continuum model PCM model were sensibly able to predict the excitation energies, the spectroscopy of the compounds. HOMO and LUMO energy levels of these molecules can make a positive impact on the process of electron injection and dye regeneration. Gaps energy ΔE g , short-circuit current density J sc , light-harvesting efficiency LHE, injection driving force ΔG inject , total reorganization energy λ total and open-circuit photovoltage V oc enable qualitative predictions about the reactivity of these dyes.

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“…The experimental results reached for organic molecules without minerals remain limited to date. As some of the studies works only searched the optoelectronic and photophysical properties for dye sensitizers [24,25], also intra molecule e --dynamic process between compounds and TiO2 [26,27]. The central quinoxalinedione has been paired to (CH3, Cl, NO2 and hydroxiquinolinyl), and bonded to the substituent as an Acceptor/anchor group forming D-π-A designing.…”

Section: Introductionmentioning

confidence: 99%

Optical and Photovoltaic Properties of New Synthesized Quinoxaline-2,3 Dione Derivatives for Efficient Dye Sensitized Solar Cell Application

et al. 2022

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In this study, the synthesis of 4 new heterocyclic compounds derived from quinoxalinedione were presented, which have been characterized by 1H and 13C NMR spectroscopy. The solar cells’ photovoltaic properties based on these novels organic compounds donor-π-acceptor dyes were studied. Density functional theory DFT method is realized to optimize electronic parameters, optical and photovoltaic properties for some new 8-hydroxyquinoline derivatives based on quinoxaline-2,3-dione. The results have shown that time-dependent DFT (TDDFT) investigations with polarizable continuum model PCM were significantly able to foretell the excitation energy and the spectroscopy of the molecule. The highest occupied molecular orbital HOMO and the lowest unoccupied molecular orbital LUMO energy levels of these molecules can ensure a positive impact on the dye regeneration and electron injection process. Injection driving force ΔGinject, light-harvesting efficiency LHE, reorganization energy λtotal and open-circuit photovoltage Voc provide qualitative predictions on these dyes’ reactivity. Among these 4 molecules, the compounds which can be used as organic solar cells have determined. HIGHLIGHTS We presented the synthesis and the characterization of a new series of heterocyclic compounds obtained by association of 8-hydroxyquinoline with quinoxalindione derivatives. The synthesis of this series of compounds was carried out by simple conditions but with good yields and the characterization data shows that there is good consistency between the spectroscopic data and the proposed structures These new compounds were obtained according to simple procedures with good yields and they have been the subject of a theoretical study This investigated process can be employed to predict the optical and photovoltaics properties on the other compounds and polymers, and it encourages to synthesis the novel organic solar cell materials GRAPHICAL ABSTRACT

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Organic Chromophores Based on a Fused Bis‐Thiazole Core and Their Application in Dye‐Sensitized Solar Cells

Cited by 6 publications

References 1 publication

New Blue Donor–Acceptor Pechmann Dyes: Synthesis, Spectroscopic, Electrochemical, and Computational Studies

New Blue Donor–Acceptor Pechmann Dyes: Synthesis, Spectroscopic, Electrochemical, and Computational Studies

Theoretical investigation using DFT of quinoxaline derivatives for electronic and photovoltaic effects

Optical and Photovoltaic Properties of New Synthesized Quinoxaline-2,3 Dione Derivatives for Efficient Dye Sensitized Solar Cell Application

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