Heteroleptic Ruthenium Sensitizers with Hydrophobic Fused‐Thio­phenes for Use in Efficient Dye‐­Sensitized Solar Cells

Lu, Zong Zhan; Peng, Jia De; Wu, An Kai; Lin, Ching Yih; Wu, Chun Guey; Ho, Keang-Po; Lin, Ying-Chih; Lu, Kuang Lieh

doi:10.1002/ejic.201501321

Cited by 22 publications

(10 citation statements)

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“…By this route, all reaction steps are performed in the same reaction flask without separation and purification of the intermediates. Since its publication, a large number of groups have adopted this procedure to prepare, mainly, cis -[Ru(NN)(dcbH 2 )(NCS) 2 ] compounds. ,− It is stated that the reaction of [Ru( p -cymene)Cl 2 ] 2 in N , N ′-dimethylformamide (DMF) with the NN ligand at 333–353 K for 2 h results in the mononuclear [Ru(NN)( p -cymene)Cl]Cl species, as shown in Figure . In the second step, dcbH 2 is added, and the temperature is increased to 423–433 K, leading to formation of the cis -[Ru(NN)(dcbH 2 )Cl 2 ] complexes.…”

Section: Introductionmentioning

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: Introductionmentioning

confidence: 99%

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

Müller

Polo

2018

Inorg. Chem.

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“…These ruthenium complexes werefor many yearsalmost exclusively polypyridine complexes with NCS – auxiliary ligands like the well-known bidentate N3/N719 or the tridentate N749 (“black dye”). On the basis of these general motifs, a plethora of bis- or trisheteroleptic sensitizers has been developed, with the intention of improving the absorption properties − (e.g., by enlarging the ligand’s π-system), hydrophobicity ,− (by adding alkyl chains), or efficient charge injection − (by optimizing the number and nature of anchor groups).…”

Section: Introductionmentioning

confidence: 99%

Ruthenium(II) Bipyridyl Complexes with Cyclometalated NHC Ligands

Schleicher

Leopold

Borrmann³

et al. 2017

Inorg. Chem.

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We present the synthesis and characterization of novel cyclometalated ruthenium N-heterocyclic carbene (NHC) complexes of the general formula [Ru(C^C*)(bpy)]PF (bpy = 2,2'-bipyridine), with the C^C* ligand being based on different 1-phenylimidazoles. They were synthesized in a one-pot procedure starting from the corresponding p-cymene NHC complexes [Ru(C^C*)(p-cymene)Cl]. Their structural, spectroscopic, and electrochemical properties were investigated by NMR, X-ray, UV/vis, and CV, as well as density functional theory methods. Because of the stronger electron-donating carbene ligands, these complexes represent a new class of bisheteroleptic dyes with improved photophysical and electrochemical properties.

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“…The solvent was removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel using hexanes as the eluent to afford compound 1 as white solid (47.7 mg, 22.3%) [54]. 1 H NMR (400 MHz, CDCl3): δ 6.92 (s, 2H), 2.86 (t, J = 7.3 Hz, 4H), 1.73 -1.66 (m, 4H), 1.40 -1.26 (m, 20H), 0.86 (t, J = 6.9 Hz, 6H) 13…”

Section: General Materials and Methodsmentioning

confidence: 99%

Development of Dithieno[3,2-b:2′,3′-d]thiophene (DTT) Derivatives as Solution-Processable Small Molecular Semiconductors for Organic Thin Film Transistors

Choi

Jang

et al. 2021

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Novel solution-processable dithieno[3,2-d:2′,3′-d]thiophene (DTT) derivatives with alkylated thiophene or alkyl chain substituents, 2,6-bis(5-octylthiophen-2-yl)dithieno[3,2-b:2′,3′-d]thiophene (compound 1), 2,6-bis(5-(2-ethylhexyl)thiophen-2-yl)dithieno[3,2-b:2′,3′-d]thiophene (compound 2), and 2,6-dioctyldithieno[3,2-b:2′,3′-d]thiophene (compound 3), have been synthesized and employed as small molecular organic semiconductors for organic field-effect transistors (OFETs). All compounds exhibited good thermal stability over 290 °C, while different side groups of DTT compounds afforded different melting temperatures. The molecular orbital energy levels were experimentally and theoretically calculated, and their trend was almost the same. The developed compounds were employed as active layers for top-contact/bottom-gate OFETs with average charge carrier mobility as high as 0.10 cm2/Vs and current on/off ratio > 107 in ambient atmosphere. Notably, DTT derivative with linear alkyl chain (-octyl) substituents showed the best device performance. High device performance could be attributed to the large grains and continuous surface coverages as well as high film texture of the corresponding semiconductor films.

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Heteroleptic Ruthenium Sensitizers with Hydrophobic Fused‐Thiophenes for Use in Efficient Dye‐Sensitized Solar Cells

Cited by 22 publications

References 76 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

Ruthenium(II) Bipyridyl Complexes with Cyclometalated NHC Ligands

Development of Dithieno[3,2-b:2′,3′-d]thiophene (DTT) Derivatives as Solution-Processable Small Molecular Semiconductors for Organic Thin Film Transistors

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Heteroleptic Ruthenium Sensitizers with Hydrophobic Fused‐Thio­phenes for Use in Efficient Dye‐­Sensitized Solar Cells

Cited by 22 publications

References 76 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

Ruthenium(II) Bipyridyl Complexes with Cyclometalated NHC Ligands

Development of Dithieno[3,2-b:2′,3′-d]thiophene (DTT) Derivatives as Solution-Processable Small Molecular Semiconductors for Organic Thin Film Transistors

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Heteroleptic Ruthenium Sensitizers with Hydrophobic Fused‐Thiophenes for Use in Efficient Dye‐Sensitized Solar Cells