Stable Dyes Containing Double Acceptors without COOH as Anchors for Highly Efficient Dye‐Sensitized Solar Cells

Mao, Jiangyi; He, Nannan; Ning, Zhijun; Zhang, Qiong; Guo, Fuling; Chen, Long; Wu, Wenjun; Hua, Jing; Tian, He

doi:10.1002/anie.201204948

Cited by 180 publications

(99 citation statements)

References 41 publications

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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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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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“…6, the Nyquist plots showed the radius of the semicircle corresponding to the working electrode to be higher for FTO/TiO 2 /JY03 compared to FTO/TiO 2 /JY01 and FTO/TiO 2 /JY02 indicating that the electron recombination resistance increased for JY03 modified electrodes. A large R ct is always preferable, indicating that the electron recombination in the devices are strongly reduced and therefore a smaller dark current and a larger value of opencircuit photovoltage [35,36]. The fitted R ct increased in the order of JY02 (53 U) < JY01 (84 U) < JY03 (130 U).…”

Section: Electrochemical Impedance Spectroscopymentioning

confidence: 90%

6H-Indolo[2,3-b]quinoxaline-based organic dyes containing different electron-rich conjugated linkers for highly efficient dye-sensitized solar cells

Qian

Gao

Zhu

et al. 2015

Journal of Power Sources

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“…Based on the rhodanine moiety in which the lactam configuration could transfer α-hydrogen to form equilibrium with its enol tautomer. [17] We speculated that the decrease of υ C O , υ N H & δ N H and υ C N may originate from the isomerization of hydantoin anchor in HY-3 and HY-4. The broad peak at ≈1715 cm −1 could be assigned to the hybrid peaks of C N (enol tautomer) and C O stretching vibrations.…”

Section: Adsorption Mechanismmentioning

confidence: 99%

Metal‐Free Sensitizers Containing Hydantoin Acceptor as High Performance Anchoring Group for Dye‐Sensitized Solar Cells

Guo

Liu

et al. 2016

Adv Funct Materials

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The anchoring group in dye‐sensitized solar cells (DSSCs) profoundly affects the electron injection and durability on TiO2 films interface. Here, the hydantoin acceptor is introduced as anchoring group for DSSCs. The hydantoin based sensitizer achieves a photovoltaic efficiency of 7.66%, compared to 4.90% for sensitizer containing the conventional cyanoacrylic acid as anchoring group. Remarkably, the hydantoin anchoring group significantly enhances the electron‐injection efficiency (Φinj) and photocurrent (Jsc). The time dependent adsorption and desorption data indicate the strong binding strength and the superiority of stability for hydantoin based sensitizers. The Fourier transform infrared measurements investigate the adsorption mechanism of hydantoin on TiO2 interface. These results strongly corroborate the advantages of incorporating hydantoin as acceptor and anchoring group. As a consequence, the sensitizer HY‐4 with hydantoin approaches the photovoltaic efficiency of 8.32% under 0.1 sunlight illumination. These observations offer a new route to design and develop efficient sensitizers for DSSCs.

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Stable Dyes Containing Double Acceptors without COOH as Anchors for Highly Efficient Dye‐Sensitized Solar Cells

Abstract: The electron acceptor 2-(1,1-dicyanomethylene) rhodanine is a promising alternative to cyanoacrylic acid as an anchoring group for organic dyes. For example, the RD-II-based dye-sensitized solar cell has an overall conversion efficiency of 7.11 % and long-term stability.

Cited by 180 publications

References 41 publications

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

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

6H-Indolo[2,3-b]quinoxaline-based organic dyes containing different electron-rich conjugated linkers for highly efficient dye-sensitized solar cells

Metal‐Free Sensitizers Containing Hydantoin Acceptor as High Performance Anchoring Group for Dye‐Sensitized Solar Cells

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