Dye‐Sensitized Solar Cells Based On Donor–Acceptor π‐Conjugated Fluorescent Dyes with a Pyridine Ring as an Electron‐Withdrawing Anchoring Group

Ooyama, Yousuke; Inoue, Shogo; Nagano, Tomoya; Kushimoto, Kohei; Ohshita, Joji; Imae, Ichiro; Komaguchi, Kenji; Harima, Yutaka

doi:10.1002/anie.201102552

Cited by 250 publications

(140 citation statements)

References 27 publications

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“…When the dyes 3a-c were adsorbed on the TiO 2 surface, the stretching hands observed at 1517-1537 and 1569-1573 cm −1 have disappeared and a new strong band appeared at 1599-1600 cm −1 , which can be assigned to pyrimidinyl groups coordinated to the Lewis acid sites on the TiO 2 surface. These consequences are in good agreement with a similar behavior of the pyridinyl anchoring group [44][45][46][47][48][49][50] and with our previous results for the pyrimidinyl anchoring group [13].…”

Section: Photophysical and Electrochemical Propertiessupporting

confidence: 91%

Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety

et al. 2015

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Novel donor-π-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in six aprotic solvents of various polarities have been studied by ultraviolet-visible and fluorescence spectroscopy. In contrast to the absorption spectra, fluorescence emission spectra displayed a strong dependence from their solvent polarities. The nature of the observed long wavelength maxima has been elucidated by means of quantum chemical calculations. The electrochemical properties of these dyes have been investigated by using cyclic voltammetry, while their photovoltaic performance was evaluated by a device fabrication study. The experimental and calculation data show that all of the dyes can be regarded as potentially good photosensitizers for dye-sensitized solar cells.

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Section: Photophysical and Electrochemical Propertiessupporting

confidence: 91%

Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety

et al. 2015

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“…The main objective of the present study was to determine whether photofunctional dyads such as 4 were efficient when attached to TiO 2 for electron photoinjection into the semiconductor. The most common method for attachment of light absorbers to TiO 2 nanoparticles is through various anchoring groups such as carboxylate, phosphonate, sulfonate, salicylate, acetylacetonate, catecholate, and hydroxamate (59)(60)(61)(62)(63)(64). In the present study, with phosphonate esters and carboxylate esters as diimine substituents on PtN 2 S 2 chromphores and dyads, attempts to hydrolyze the esters prior to TiO 2 attachment proved problematic because of poor stability of the PtN 2 S 2 moiety under the hydrolysis conditions.…”

Section: Resultsmentioning

confidence: 99%

Light-driven generation of hydrogen: New chromophore dyads for increased activity based on Bodipy dye and Pt(diimine)(dithiolate) complexes

Zheng

Sabatini

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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New dyads consisting of a strongly absorbing Bodipy (dipyrromethene-BF 2 ) dye and a platinum diimine dithiolate (PtN 2 S 2 ) charge transfer (CT) chromophore have been synthesized and studied in the context of the light-driven generation of H 2 from aqueous protons. In these dyads, the Bodipy dye is bonded directly to the benzenedithiolate ligand of the PtN 2 S 2 CT chromophore. Each of the new dyads contains either a bipyridine (bpy) or phenanthroline (phen) diimine with an attached functional group that is used for binding directly to TiO 2 nanoparticles, allowing rapid electron photoinjection into the semiconductor. The absorption spectra and cyclic voltammograms of the dyads show that the spectroscopic and electrochemical properties of the dyads are the sum of the individual chromophores (Bodipy and the PtN 2 S 2 moieties), indicating little electronic coupling between them. Connection to TiO 2 nanoparticles is carried out by sonication leading to in situ attachment to TiO 2 without prior hydrolysis of the ester linking groups to acids. For H 2 generation studies, the TiO 2 particles are platinized (Pt-TiO 2 ) so that the light absorber (the dyad), the electron conduit (TiO 2 ), and the catalyst (attached colloidal Pt) are fully integrated. It is found that upon 530 nm irradiation in a H 2 O solution (pH 4) with ascorbic acid as an electron donor, the dyad linked to Pt-TiO 2 via a phosphonate or carboxylate attachment shows excellent light-driven H 2 production with substantial longevity, in which one particular dyad [4(bpyP)] exhibits the highest activity, generating ∼40,000 turnover numbers of H 2 over 12 d (with respect to dye).photochemistry | solar energy conversion | hydrogen | spectroscopy | synthesis W ater splitting into hydrogen and oxygen is the key energystoring reaction of artificial photosynthesis (AP) and one of the most promising long-term strategies for carbon-free energy on a potentially global scale (1). As a redox reaction, water splitting has been studied primarily in terms of its two halfreactions, the reduction of aqueous protons to H 2 and the oxidation of water to O 2 (2-13). Whereas some of these studies date back more than 30 y (14-22), recent progress on each halfreaction has been notable, particularly with regard to catalyst development and mechanistic understanding of each transformation (6,(23)(24)(25)(26)(27)(28)(29). In this paper, we focus on efforts dealing with the lightdriven generation of H 2 , which in its simplest form requires a light absorber or photosensitizer (PS) for electron-hole creation, a means or pathway for charge separation and electron transfer, an aqueous proton source, a catalyst for collecting electrons and protons and promoting their conversion to H 2 , and an ultimate source of electrons in the form of an electron donor.Dating from the earliest work on the light-driven generation of H 2 , the photosensitizer has most often been a Ru(II) complex with 2,2′-bipyridine (bpy) and/or related heterocyclic ligands having a long-lived triplet metal-to-ligand ...

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“…2), which would be impossible in the case of isomer DF13A. This observation is not surprising, considering that even the simple pyridine ring has been reported to serve as anchoring group [14]. Based on these observations, device stability tests were also conducted on larger area, transparent cells, which indeed showed that devices built using compounds DF13B and DF13C retained their efficiency after 930 h of continuous simulated solar irradiation at 50 °C [27].…”

Section: Stability Tests Of the Dyesmentioning

confidence: 78%

“…2, right), which have interested various research groups. For instance, several dyes with a simple pyridine acceptor group have been prepared and showed to maintain a good charge injection efficiency in comparison with the corresponding carboxylic acids, although photovoltaic efficiencies often turned out to be only moderate at best [14][15][16][17][18][19][20]. Furthermore, a single example of a 2-carboxy-pyridine anchoring group was described, together with other heterocyclic, carboxylate-anchored, nitrogen-containing acceptors [21].…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of organic sensitizers with enhanced anchoring stability in dye-sensitized solar cells

Reginato

Calamante

Zani

et al. 2017

Pure and Applied Chemistry

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D-π-A dyes have received a special attention in the field of dye-sensitized solar cells (DSSCs). In this kind of molecules, the acceptor group (A) generally acts as an anchor, enabling the adsorption of the dye onto the metal oxide substrate (TiO 2 ) and providing a good electron injection. The search for new anchors represents a critical factor for the development of improved DSSCs and in recent years has been a very active research field. This mini-review focuses especially on our work on pyridine-derived anchoring groups for D-π-A dyes, with a special regard on the preparation and characterization of three different families of dyes and a critical evaluation of their stability and efficiency.

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Dye‐Sensitized Solar Cells Based On Donor–Acceptor π‐Conjugated Fluorescent Dyes with a Pyridine Ring as an Electron‐Withdrawing Anchoring Group

Cited by 250 publications

References 27 publications

Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety

Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety

Light-driven generation of hydrogen: New chromophore dyads for increased activity based on Bodipy dye and Pt(diimine)(dithiolate) complexes

Design and synthesis of organic sensitizers with enhanced anchoring stability in dye-sensitized solar cells

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