Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells

Meyer, T.; Ogermann, Daniel; Pankrath, Andrea; Kleinermanns, Karl; Müller, Thomas J. J.

doi:10.1021/jo202608w

Cited by 91 publications

(67 citation statements)

References 66 publications

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“…They also exhibit slight red shifts due to their extended conjugations. Phenothiazine derivatives with extended π ‐conjugated substituents often display intense luminescence upon UV/vis excitation with Stokes shifts that might be due to solvent relaxation and, in part, to geometry changes in the excited state . The electronic properties of these compounds have led to their applications as electrophore probes in supramolecular assemblies for photoinduced electron transfer and sensor studies and as electron‐donor components in material scientific investigations such as electrically conducting charge‐transfer composites, polymers, Do‐Acc arrangements, and also as chromophores in dye‐sensitized photovoltaic cells .…”

Section: Resultsmentioning

confidence: 99%

“…Besides their well‐known physiological activity profile, because of their reversible oxidative reactions, which give rise to characteristic, deep colored radical cation absorptions, more recently, phenothiazine derivatives have become attractive spectroscopic probes in molecular arrangements for photoinduced electron transfer studies and as scientific motif materials . Also, recent reports revealed that phenoxazine derivatives are widely applied as organic light emitting diodes .…”

Section: Introductionmentioning

confidence: 99%

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Rapid Access to New Angular Phenothiazine and Phenoxazine Dyes

Onoabedje

Okoro

Knight

2015

Journal of Heterocyclic Chem

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The synthesis of some new thiophenyl-derivatized and furanyl-derivatized phenothiazine and phenoxazine dyestuffs is described. This was achieved by two methods after the synthesis of 6-chloro-5H-benzo[a]phenothiazin-5-one, 6-chloro-5H-benzo[a]phenoxazin-5-one, and 6-chloro-5H-naphtho [2,1-b] pyrido [2,3-e][1,4]oxazin-5-one intermediates via anhydrous base condensation reaction of 2,3-dichloro-1,4-naphthoquinone with 2-aminothiophenol, 2-aminophenol, and 2-aminopyridinol, respectively. The first method involved treatment of tributyl(thien-2-yl) or tributyl(furan-2-yl) stannane with chlorophe nothiazine/chlorophenoxazine under mild basic chemical formula (CsF) and 1,4-dioxane or toluene solvent at 80°C to supply dazzling yellow solid in high yields. In the second method, the catalytic system was preactivated in acetonitrile, followed by addition of coupling partners and K3PO4 to obtain high melting and variety of highly colored products in moderate to high yields. The reaction conditions were compatible with unprotected N-H and carbonyl functional groups. The intense colors of these dyes and their ease of re-oxidation of Na2S2O4-reduced derivatives make them suitable as vat dyes. Also, they were found to be good colorants for textiles, papers, paint, ink, soap, polish, candle, and plastic materials.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Rapid Access to New Angular Phenothiazine and Phenoxazine Dyes

Onoabedje

Okoro

Knight

2015

Journal of Heterocyclic Chem

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“…The cyclic voltammograms recorded for the dyes are displayed in Fig. 49,19 In the present compounds, the anodic shift of the oxidation potentials is attributed to the electron-withdrawing effect of the benzimidazole unit. All the dyes exhibited a quasi-reversible oxidation couple attributable to the removal of electron from the phenothiazine segment.…”

Section: Electrochemical Characteristicsmentioning

confidence: 88%

Phenothiazine-based bipolar green-emitters containing benzimidazole units: synthesis, photophysical and electroluminescence properties

et al. 2015

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A series of bipolar green emitters bearing hole-transporting phenothiazine and electron-transporting Nphenylbenzimidazole are synthesized and characterized by their photophysical, electrochemical and thermal properties. All the dyes exhibited solvent dependent emission characteristics indicative of more polarized excited state probably arising from the enhanced intramolecular charge transfer (ICT) character in the photo-excited state. Dyes possessing two N-phenylbenzimidazole units and pyridine showed larger degree of ICT in the excited state than the remaining dyes as evidenced from the huge solvatochromic shifts in emission spectra. The dyes exhibited facile oxidation attributable to the removal of electron predominantly from the phenothiazine donor. However, the oxidation is positively shifted due to the electronic perturbations arising from the electron-withdrawing N-phenylbenzimidazole and pyridine units. The compounds exhibited marked thermal stability with the high decomposition temperatures in the range, 412-454 °C. Solution processed organic light-emitting diodes fabricated using the dyes as neat hole-transporting emitting layer or dopant emitter in CBP host showed promising device parameters. A dye possessing three phenothiazine units exhibited bright green electroluminescence with maximum luminance of 1,365 cd/m 2 , CIE coordinates (0.314, 0.593) resembling the prescribed NTSC 1987 standards with a current efficiency of 1.9 cd/A at 100 cd/m 2 .

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“…The best results have been achieved with CdS 6 Se 1 with an absorption up to 800 nm [7]. In principle, organic dyes can be used for sensitisation as well [10][11][12] and results obtained with this class of sensitisers for water splitting with solar light will be published elsewhere [13].…”

Section: Introductionmentioning

confidence: 97%

Solar Water Splitting by Semiconductor Nanocomposites and Hydrogen Storage with Quinoid Systems

Wilke¹,

Schricker²,

Rolf³

et al. 2012

OJPC

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Photocatalytic splitting of water was carried out in a two-phase system. The efficiencies of different types of nanocrystalline semiconductors were investigated and compared with commercialised TiO 2 nanopowder. Generated hydrogen was chemically stored by use of a quinoid system, which seems to be useable for fuel cells. Solar light sensitive nanocomposites of CdSe/TiO 2 and CdS x Se y /TiO 2 type were prepared and their good photocatalytic performance was demonstrated. In the visible range of 400 -600 nm CdS x Se y /TiO 2 composites show comparable good results as in the UV range, which is very promising for their use as solar light water splitters. The concept of sensitising TiO 2 with different kind of semiconductor nanoparticles, which is already known from quantum dot sensitised solar cells (QDSC), was demonstrated here for water splitting as well. Furthermore the kinetics of the storage reaction was investigated by UV-Vis spectroscopy and found to proceed via a consecutive reaction with an 1:1 charge transfer complex of quinone and hydroquinone as intermediate. The electron transfer process via a Fe 2+ /Fe 3+ redox couple was investigated by UV-Vis spectroscopy as well as by a dye reaction on the TiO 2 surface. A light microscopic view of the surface of larger aggregates of TiO 2 nanoparticles indicated different areas of photocatalytic activity with photocatalysis preferentially at catalyst edges. The global electron transfer process could be traced by following the dye colour in real time.

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Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells

Cited by 91 publications

References 66 publications

Rapid Access to New Angular Phenothiazine and Phenoxazine Dyes

Rapid Access to New Angular Phenothiazine and Phenoxazine Dyes

Phenothiazine-based bipolar green-emitters containing benzimidazole units: synthesis, photophysical and electroluminescence properties

Solar Water Splitting by Semiconductor Nanocomposites and Hydrogen Storage with Quinoid Systems

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