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Macromolecular Chemistry I:

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Willinger, K.; Fischer, K.; Kisselev, R.; Thelakkat, M.: Synthesis, spectral, electrochemical and photovoltaic properties of novel heteroleptic polypyridyl ruthenium(II) donor-antenna dyes, Journal of Materials Chemistry, 19, 5364 - 5376 (2009) -- DOI: 10.1039/b901988j
Key words: B4
Abstract:
A series of new heteroleptic Ru(II)(4,4-dicarboxylic acid-2,2-bipyridine)(bipyridyl donor-antenna ligand)(NCS)2 complexes carrying different donor-antenna moieties was designed, synthesised and characterised. A general synthetic procedure was used for the covalent attachment of the donor-antenna units 1,3-di(2-thienyl)benzo[c]-thiophene (DTBT), trans-stilbene (tS) and 4-{2-[2-(2-methoxyethoxy)ethoxy]-ethoxy}-N,N-diphenylbenzenamine (TPA-EO) to 2,2-bipyridine. First, a Vilsmeier-Haack reaction was applied to get the respective aldehyde-functionalised donor-antenna compounds which secondly reacted with 4,4-bis(triphenylphosphonium-methyl)-2,2-bipyridyl chloride under Wittig conditions to give the desired bipyridyl donor-antenna molecules. To create a dimethylamino (NMe2) substituted donor-antenna compound a reaction between 4,4-dimethyl-2,2-bipyridine and Bredereck's reagent was carried out. The final Ru(II) complexes referred to as Ru-DTBT-NCS, Ru-tS-NCS, Ru-TPA-EO-NCS and Ru-NMe2-NCS were obtained via one-pot reactions, starting from dichloro(p-cymene)ruthenium(II) dimer. The bipyridyl donor-antenna molecules as well as the complexes were fully characterised and their optical and electrochemical properties were studied in detail. Preliminary tests of the novel Ru(II)bis(bipyridyl)(NCS)2 dyes in solid-state dye-sensitized solar cells under AM1.5G conditions (100 mW cm-2) yielded short-circuit current densities of 1.06, 2.15, 3.42 and 4.03 mA cm-2, open-circuit voltages of 625, 635, 685 and 735 mV and fill factors of about 45% corresponding to overall efficiencies of 0.31, 0.58, 0.99 and 1.37% for Ru-DTBT-NCS, Ru-NMe2-NCS, Ru-tS-NCS and Ru-TPA-EO-NCS, respectively.
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