Effect of Extended Conjugation of N-Heterocyclic Carbene-Based Sensitizers on the Performance of Dye-Sensitized Solar Cells

Akula, Suri Babu; Chen, Huei Siou; Su, Chun‐Hsi; Chen, Bo Ren; Chiou, Jiunn Jie; Shieh, Chia Hsuan; Lin, Ya Fen; Li, Wen Ren

doi:10.1021/acs.inorgchem.7b01714

Cited by 13 publications

(4 citation statements)

References 71 publications

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“…Ruthenium(II) polypyridyl compounds have been widely employed for several applications, notably in energy conversion processes, e.g., in artificial photosynthetic systems, , light-emitting devices, or solar cells. , Changes in the size and electronic features of the ligands are carried out to tune the properties of the complexes, such as light absorption, redox potential, reactivity, and energy level alignment, aiming to improve the efficiency of such devices . For the efficient preparation of these compounds, it is necessary to develop and understand the synthetic methods that allow the synthesis of coordination compounds that exhibit the properties required for a particular application in an easy and versatile way.…”

Section: Resultsmentioning

confidence: 99%

Mechanistic Insights into the Stepwise Assembly of Ruthenium(II) Tris-heteroleptic Compounds

Müller

Polo

2018

Inorg. Chem.

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The ruthenium(II) tris-heteroleptic compounds cis-[Ru(NN)(dcbH2)(NCS)2], NN = polypyridyl ligand and dcbH2 = 2,2′-bipyridine-4,4′-dicarboxylic acid, can be synthesized by a one-pot route starting from [Ru(p-cymene)Cl2]2, followed by the sequential addition of ligands. In this work, each synthetic step for the cis-[Ru(R-phen)(dcbH2)(NCS)2] (R = H, Me, Ph, MeO, or Cl) preparation was individually investigated, aiming to identify reaction intermediates and to establish correlations among temperature, reaction time, reactant concentration, and the identity of the substituent of the polypyridyl ligand with the kinetics of the reactions and distribution of the products. The first step is the cleavage of [Ru(p-cymene)Cl2]2, followed by the coordination of R-phen via an associative mechanism and establishment of a direct correlation between the electron-donating or electron-withdrawing character of R and the reaction rates. The second step is the conversion of [Ru(R-phen)(p-cymene)Cl]Cl to cis-[Ru(R-phen)(dcbH2)Cl2], and the rate-determining step is the formation of the intermediate [Ru(R-phen)Cl2], which exhibits a low dependence on R. The last step is the substitution of Cl– by NCS–, and the N-bound isomer is the major product. The reaction temperature, time, and identity of R influence the relative distribution of the linkage isomers. The comprehension of each of these processes is a key factor to develop new strategies to optimize the one-pot synthetic route.

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Section: Resultsmentioning

confidence: 99%

Mechanistic Insights into the Stepwise Assembly of Ruthenium(II) Tris-heteroleptic Compounds

Müller

Polo

2018

Inorg. Chem.

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“…The first type ( Figure 1 a) is N^C^N ligands containing two benzimidazole fragments, such as 2,6-bis(benzimidazol-2-yl)benzene [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. The second type is C^N ligands ( Figure 1 b), where the Ru-C bond is formed with the imidazole fragment and one of the imidazole nitrogen is bonded to a pyridine [ 27 , 38 ]. The third type is the N^N ligands of the 2-benzimidazol-2-yl-pyridines class ( Figure 1 c) [ 27 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 ].…”

Section: Introductionmentioning

confidence: 99%

“…Complexes with ligands of the second type ( Figure 1 b) have also been studied as sensitizers for DSSC [ 38 ]. For example, the authors of [ 38 ] studied the effect of the size of the conjugated system of C^N-ligand on the photosensitizer efficiency.…”

Section: Introductionmentioning

confidence: 99%

Fine-Tuning of the Optical and Electrochemical Properties of Ruthenium(II) Complexes with 2-Arylbenzimidazoles and 4,4′-Dimethoxycarbonyl-2,2′-bipyridine

Lavrova,

Verzun,

Mishurinskiy

et al. 2023

Molecules

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A series of cyclometalated complexes of ruthenium (II) with four different substituents in the aryl fragment of benzimidazole was synthesized in order to study the effect of substituent donation on the electronic structure of the substances. The resulting complexes were studied using X-ray diffraction, NMR spectroscopy, MALDI mass spectrometry, electron absorption spectroscopy, luminescence spectroscopy, and cyclic voltammetry as well as DFT/TDDFT was also used to interpret the results. All the complexes have intense absorption in the range of up to 700 nm, the triplet nature of the excited state was confirmed by measurement of luminescence decay. With an increase in substituent donation, a red shift of the absorption and emission bands occurs, and the lifetime of the excited state and the redox potential of the complex decrease. The combination of these properties shows that the complexes are excellent dyes and can be used as photosensitizers.

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“…In an independent study, Zhang and co-workers reported the synthesis of phenanthro-imidazole 1 (Figure 1) and used it for OLEDs [24]. More recently, Akula and coworkers have reported the synthesis of ruthenium complex 2, revealing good optical, electrochemical, and thermal properties, which has been used as a promising electron-transport material for organic solar cells [25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical properties of new reactive fluorophenanthrenes

Hajri¹,

Albalawi²,

Elsayed³

et al. 2020

Comptes Rendus. Chimie

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A series of six new suitably functionalized fluorophenanthrene derivatives were synthesized through a simple procedure, making use of inexpensive starting materials under mild conditions. The target phenanthrenes were characterized by 1 H and 13 C NMR and FT-IR spectroscopies. UV-Vis absorption and photoluminescence of these phenanthrenes were evaluated in solutions. A notable behavior and a strong fluorescence in the blue region of the visible spectrum were observed, making them potential candidates for organic light-emitting diode technology or advanced materials. Their electrochemical behavior was also experimentally examined in solution, demonstrating an important charge transfer interaction owing to their π-conjugated electronic system. Résumé. Une série de six nouveaux dérivés de fluorophénanathrène convenablement fonctionnalisés ont été synthétisés selon une procédure simple utilisant des réactifs peu coûteux dans des conditions douces. Les phénanthrènes cibles ont été caractérisés par RMN 1 H et 13 C et IR à transformée de Fourrier. L'étude de l'absorption UV-Vis et de la photoluminescence de ces phénanthrènes a été évaluée en solution montrant un comportement notable et une forte fluorescence dans la région bleue du spectre visible, ce qui permet de les considérer comme des candidats potentiels pour la technologie OLED ou des matériaux avancés. Leur comportement électrochimique a été aussi examiné expérimentalement en solution démontrant une interaction de transfert de charge importante grâce à leur système électronique π-conjugué.

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Effect of Extended Conjugation of N-Heterocyclic Carbene-Based Sensitizers on the Performance of Dye-Sensitized Solar Cells

Cited by 13 publications

References 71 publications

Mechanistic Insights into the Stepwise Assembly of Ruthenium(II) Tris-heteroleptic Compounds

Mechanistic Insights into the Stepwise Assembly of Ruthenium(II) Tris-heteroleptic Compounds

Fine-Tuning of the Optical and Electrochemical Properties of Ruthenium(II) Complexes with 2-Arylbenzimidazoles and 4,4′-Dimethoxycarbonyl-2,2′-bipyridine

Synthesis and photophysical properties of new reactive fluorophenanthrenes

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