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Synthesis of Amphiphilic Ru(II) Heteroleptic Complexes Based on Benzo[1,2-b:4,5-b']dithiophene: Relevance of the Half-Sandwich Complex Intermediate and Solvent Compatibility.

Synthesis of Amphiphilic Ru(II) Heteroleptic Complexes Based on Benzo[1,2-b:4,5-b']dithiophene: Relevance of the Half-Sandwich Complex Intermediate and Solvent Compatibility.

Chemistry (Weinheim an der Bergstrasse, Germany) (2015-09-12)

Maxence Urbani, María Medel, Sangeeta Amit Kumar, Mine Ince, Ashok N Bhaskarwar, David González-Rodríguez, Michael Grätzel, Mohammad Khaja Nazeeruddin, Tomás Torres

ABSTRACT

The detailed synthesis and characterization of four ruthenium(II) complexes [RuLL'(NCS)2 ] is reported, in which L represents a 2,2'-bipyridine ligand functionalized at the 4,4' positions with benzo[1,2-b:4,5-b']dithiophene derivatives (BDT) and L' is 2,2'-bipyridine-4,4'-dicarboxylic acid unit (dcbpy) (NCS=isothiocyanate). The reaction conditions were adapted and optimized for the preparation of these amphiphilic complexes with a strong lipophilic character. The photovoltaic performances of these complexes were tested in TiO2 dye-sensitized solar cell (DSSC) achieving efficiencies in the range of 3-4.5 % under simulated one sun illumination (AM1.5G).

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Toluene, Laboratory Reagent, ≥99.3%

Sigma-Aldrich

Toluene, ACS reagent, ≥99.5%

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Toluene, LR, ≥99%

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Toluene, AR, ≥99.5%

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Toluene, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.7% (GC)

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Hexane, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99% (GC)

Supelco

Ammonium thiocyanate, 99.99% trace metals basis

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n-Butyllithium solution, 2.0 M in cyclohexane

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Methanol-¹²C, 99.95 atom % ¹²C

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Hexane, anhydrous, 95%

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Toluene, anhydrous, 99.8%

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Methanol solution, NMR reference standard, 4% in methanol-d₄ (99.8 atom % D), NMR tube size 3 mm × 8 in.

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Methanol solution, (Methanol:Dimethyl sulfoxide 1:1 (v/v))

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Methanol solution, contains 0.50 % (v/v) triethylamine

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Toluene, ACS reagent, ≥99.5%

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Toluene, ACS reagent, ≥99.5%

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Hexane, ReagentPlus^®, ≥99%

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Hexane, Laboratory Reagent, ≥95%

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Toluene, suitable for HPLC, ≥99.8%

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Sodium dodecyl sulfate solution, BioUltra, for molecular biology, 10% in H₂O

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Sodium dodecyl sulfate solution, BioUltra, for molecular biology, 20% in H₂O

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Ammonium thiocyanate, ACS reagent, ≥97.5%

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2,2′-Bipyridine-4,4′-dicarboxylic acid, 98%

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Lithium iodide, AnhydroBeads^™, −10 mesh, 99.99% trace metals basis

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Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%

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Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free