- Supercritical carbon dioxide as a solvent for deposition of a tailored dye in dye sensitized solar cells
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We report a new technique whereby dyes can be deposited onto metal oxide surfaces using supercritical carbon dioxide (scCO2) for use in solar cell applications. This process eliminates the need for hazardous organic solvents and waste solvents generated during the dyeing process. The solubility of a perylene anhydride dye in scCO2 is enhanced by the incorporation of fluorinated alkyl subsituents and the use of masked carboxylic binding groups. This allows fast deposition of the dye onto the TiO2 photoanode, resulting in efficient photovoltaic performance. The unreacted dye is then easily recovered in a solid form after the deposition process by venting the carbon dioxide.
- Maniam, Subashani,Holmes, Andrew B.,Krstina, Julia,Leeke, Gary A.,Collis, Gavin E.
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supporting information; experimental part
p. 3329 - 3332
(2012/02/01)
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- SYNTHESIS OF PERYLENE-PORPHYRIN BUILDING BLOCKS AND POLYMERS THEREOF FOR THE PRODUCTION OF LIGHT-HARVESTING ARRAYS
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The present invention provides methods, compounds, and compositions for the synthesis of light harvesting arrays, such arrays comprising: (a) a first substrate comprising a first electrode; and (b) a layer of light harvesting rods electrically coupled to said first electrode, each of said light harvesting rods comprising a polymer of Formula (I): wherein m is at least 1; X1 is a charge separation group, and X2 through Xm+1 are chromophores. At least one of X2 through Xm+1 has at least one perylene group coupled thereto.
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Page 63-64, 66
(2008/06/13)
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- Practical synthesis of perylene-monoimide building blocks that possess features appropriate for use in porphyrin-based light-harvesting arrays
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Perylene-monoimide dyes with solubilizing aryloxy substituents at the perylene perimeter and a synthetic handle on the N-aryl group are valuable building blocks for incorporation as accessory pigments in porphyrin-based light-harvesting arrays. A family of such dyes has been prepared by reaction of 1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboxylic anhydride with a set of 4-iodo/ethynyl anilines (with or without 2,6-diisopropyl substituents) in the presence of Zn(OAc)2·2H2O in imidazole/mesitylene at 130°C. The workup procedures throughout the synthesis have been streamlined for scale-up purposes, minimizing chromatography. Two bis(perylene)porphyrin building blocks were prepared in a rational manner and examined in Sonogashira and Glaser polymerizations. The two isopropyl groups on the N-aryl group and the three 4-tert-butylphenoxy groups at the perylene perimeter are essential for high solubility of the bis(perylene)porphyrins and corresponding oligomers in organic solvents.
- Tomizaki, Kin-Ya,Thamyongkit, Patchanita,Loewe, Robert S.,Lindsey, Jonathan S.
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p. 1191 - 1207
(2007/10/03)
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- Electrochemistry, spectroscopy and electrogenerated chemiluminescence of perylene, terrylene, and quaterrylene diimides in aprotic solution
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The electrochemistry, UV-vis spectrophotometry, photoluminescence, and electrogenerated chemiluminescence (ECL) of perylenedicarboxylic imide, perylenetetracarboxylic diimide (PDI), terrylenetetracarboxylic diimide (TDI), and quaterrylenecarboxylic diimide (QDI) were investigated. All compounds undergo two reversible one-electron reductions and one reversible one-electron oxidation reaction. The first reduction potential shifts to less negative values and the potential for oxidation to less positive values for the diimide series with increasing size of the aromatic core. These changes in potential correlate well with orbital energies from molecular orbital calculations. The difference in potential between the first and Second reduction waves decreased with increasing distance between the imide groups, so that TDI and QDI show only a single reduction wave, equivalent to a two- electron reduction. These reduction potentials provide estimates for the equilibrium constant for disproportionation of the radical anion. Very stable ECL spectra of PDI or TDI generated by sequential production of the radical cation and radical anion at an electrode were observed; these were identical to the photoluminescence spectra A consideration of the energetics of the electron transfer reaction and the singlet energy leads to the conclusion that emission occurs mainly via generation of triplets followed by triplet- triplet annihilation (the T-route).
- Lee, Sang Kwon,Zu, Yanbing,Herrmann, Andreas,Geerts, Yves,Müllen, Kl?us,Bard, Allen J.
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p. 3513 - 3520
(2007/10/03)
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- Synthesis of Perylene-3,4-dicarboximides - Novel Highly Photostable Fluorescent Dyes
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Perylene-3,4-dicarboximides 2 are obtained by a decarboxylizing condensation of moderately sterically hindered primary amines with perylene-3,4,9,10-tetracarboxylic 3,4:9,10-bisanhydride (3) in the presence of water.Perylene-3,4-dicarboxylic anhydride (4) is prepared by hydrolysis of the imides with KOH in tert-butyl alcohol.The anhydride may be condensed with any primary amine to the corresponding imide.The imides are highly fluorescent and very photostable dyes. - Key Words: Fluorescent dyes/Pigments/Perylenes/Carboximides
- Feiler, Leonhard,Langhals, Heinz,Polborn, Kurt
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p. 1229 - 1244
(2007/10/02)
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- Synthesis of Highly Pure Perylene Fluorescent Dyes in Large Scale Amounts - Specific Preparation of Atropic Isomers
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N,N'-Bis(2,5-di-tert-butylphenyl)-3,4:9,10-perylenebis(dicarboximide) (2), an intensely coloured fluorescent dye with high photostability (Φ = 99percent, λmax = 526 nm, ε = 95000), is prepared by reaction of the corresponding amine with 3,4:9,10-perylenetetracarboxylic dianhydride and isolated in high purity even in large amounts by an extractive recrystallisation procedure.Suitable reaction conditions allow the selective preparation of each of its atropic isomers.This is interpreted in terms of different reaction mechanisms.Applications are discussed.
- Langhals, Heinz
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p. 4641 - 4645
(2007/10/02)
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- Soluble Perylene Fluorescent Dyes with High Photostability
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The preparation of several 3,4,9,10-perylenebis(dicarboximides) 1 is described and their photostability quantitatively determined and discussed.It is shown, that substitution of the insoluble perylene dye pigments with tert-butyl groups causes solubility in organic solvents leading to high quantum yields of these dyes.
- Rademacher, Andreas,Maerkle, Suse,Langhals, Heinz
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p. 2927 - 2934
(2007/10/02)
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