Iridium(III) 2‐Phenylbenzimidazole Complexes: Synthesis, Structure, Optical Properties, and Applications in Dye‐Sensitized Solar Cells

Bezzubov, Stanislav I.; Kiselev, Yuri M.; Churakov, Andrei V.; Kozyukhin, S. A.; Sadovnikov, Alexey A.; Гринберг, В. А.; Емец, В. В.; Doljenko, Vladimir D.

doi:10.1002/ejic.201501068

Cited by 38 publications

(25 citation statements)

References 31 publications

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“…The dyes based on N-phenyl benzimidazole incorporated phenothiazine created bathochromic-shifted absorption and prevented undesirable charge recombination10, which were helpful for improvement of open-circuit photovoltage. Moreover, isomeric dyes11 differed in chromophores positions, which tuned spectrum response and affected their photovoltaic properties.…”

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confidence: 99%

Photoactive layer based on T-shaped benzimidazole dyes used for solar cell: from photoelectric properties to molecular design

Song

et al. 2017

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Three benzimidazole-based organic dyes, possessing the same triphenylamine donors and cyanoacrylic acid acceptors with the bithiophene π-bridges combined in different nuclear positions of benzimidazole, were investigated in the utility of dye-sensitizer solar cells. The structure, molecular orbital and energy, absorption spectra and some important parameters (such as light harvesting efficiency (LHE), electron injection driving force, the electron injection time, chemical reactivity parameters, vertical dipole moment as well as interaction models of dye-I2) were obtained according to Newns–Anderson model and DFT calculation. The process and strength of charge transfer and separation were visualized with charge different density and index of spatial extent (S, D and Δq). Current work paid attention to the new T-shaped dyes to reveal the relation between the structure and photoelectric performance. Furthermore, nine dyes (substitution of alkyl chains and π-bridges) have been designed and characterized to screen promising sensitizer candidates with excellent photo-electronic properties.

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confidence: 99%

Photoactive layer based on T-shaped benzimidazole dyes used for solar cell: from photoelectric properties to molecular design

Song

et al. 2017

Sci Rep

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“…Thus, the replacement of 4,4'‐dicarboxy‐2,2'‐bipyridine by β‐diketone L in Ir III complexes leads to an increase in the device efficiency compared to a previously studied Ir III dye . In addition, the novel ligand used in this study provides appropriate oxidation potentials of the complexes along with an optimal triplet excited state localization and its lifetime.…”

Section: Resultsmentioning

confidence: 93%

“…It is interesting to compare absorption spectra of complexes 1–5 and those of corresponding dimeric and dcbpy‐based complexes (Figure , S22, the latter spectra were taken from ref , , …”

Section: Resultsmentioning

confidence: 99%

“…To date, cyclometalated iridium(III) complexes have proven to be excellent emitters for OLED application due to their tunable and strong luminescence, long‐lived excited states, high thermal and chemical stability . Their light‐produced excited states undergo different ways of deactivation that has been utilized in photocatalytic hydrogen systems, chemosensors, photodynamic therapy and dye‐sensitized solar cells (DSSC) . In the latter case, Ir III photosensitizers have attracted particular attention as more stable analogs of Ru II dyes .…”

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confidence: 99%

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Aromatic β‐Diketone as a Novel Anchoring Ligand in Iridium(III) Complexes for Dye‐Sensitized Solar Cells

et al. 2020

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A novel β‐diketone ligand bearing a thiophene moiety and an anchoring Ph‐COOCH3 unit has been designed, prepared and used in synthesis of cyclometalated benzimidazole‐based iridium(III) complexes for application in dye‐sensitized solar cells (DSSC). The replacement of traditional 4,4'‐dicarboxy‐2,2'‐bipyridine by this aromatic β‐diketone results in excellent tuning the redox potentials and excited state properties of these IrIII complexes, one of which exhibits good efficiency when used as a dye in DSSC. All the complexes demonstrate reversible redox behavior, with oxidation potentials (Ir4+/Ir3+) strongly depending on the electron‐donor/withdrawing nature of the substituents in the cyclometalated ligands. Surprisingly, the latter has just a little effect on their luminescence spectra, in which structured emission bands are observed. Time‐resolved spectroscopic studies in combination with DFT calculations show that the complexes emit light by mixed 3MLCT–3LC excited states predominantly composed of the diketone ligand‐centered triplet state.

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“…They are also used as ligands in constructing cyclometalated iridium(III) and ruthenium(II) complexes for organic lightemitting diodes and photosensitizers in dye-sensitized solar cells (Bezzubov et al, 2020;Lavrova et al, 2020). For the latter application, the aryl unit of these ligands should contain -electron-donating substituents to increase the lightharvesting characteristics of the corresponding organometallic complexes (Aghazada & Nazeeruddin, 2018;Bezzubov et al, 2014Bezzubov et al, , 2016. In addition, long aliphatic chains in the ligands are preferable to diminish aggregation of the complexes on the semiconductor surface (Hagfeldt et al, 2010).…”

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Synthesis and crystal structures of N-H, N-phenyl and N-benzyl-2-(4-hexyloxyphenyl)benzimidazoles

Smirnov

Tatarin

Bezzubov

2021

Acta Crystallogr E Cryst Commun

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The title compounds, 2-(4-hexyloxyphenyl)-1H-benzimidazole (C19H22N2O; 1), 2-(4-hexyloxyphenyl)-1-phenyl-1H-benzimidazole (C25H26N2O; 2) and 1-benzyl-2-(4-hexyloxyphenyl)-1H-benzimidazole (C26H28N2O; 3) were synthesized and their structures were determined by single-crystal X-ray analysis. The N-substituent at the imidazole moiety slightly affects the interplanar angle between the 4-hexyloxyphenyl ring and the benzimidazole system. The unsubstituted benzimidazole (1) forms intermolecular N—H...N bonds while in the crystal structures of 2 and 3, the molecules are assembled only through π–π and C—H...π interactions.

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Iridium(III) 2‐Phenylbenzimidazole Complexes: Synthesis, Structure, Optical Properties, and Applications in Dye‐Sensitized Solar Cells

Cited by 38 publications

References 31 publications

Photoactive layer based on T-shaped benzimidazole dyes used for solar cell: from photoelectric properties to molecular design

Photoactive layer based on T-shaped benzimidazole dyes used for solar cell: from photoelectric properties to molecular design

Aromatic β‐Diketone as a Novel Anchoring Ligand in Iridium(III) Complexes for Dye‐Sensitized Solar Cells

Synthesis and crystal structures of N-H, N-phenyl and N-benzyl-2-(4-hexyloxyphenyl)benzimidazoles

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