Solar cells based on a fullerene–azothiophene dyad

Maggini, Michele; Possamai, Giorgia; Menna, Enzo; Scorrano, Gianfranco; Camaioni, Nadia; Ridolfi, Giovanni; Casalbore-Miceli, G.; Franco, Lorenzo; Ruzzi, Marco; Corvaja, Carlo

doi:10.1039/b206275e

Cited by 47 publications

(42 citation statements)

References 12 publications

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“…Synthesis of the fullerene-chromophore conjugates: Dyads 1 b, [26] 1 d, [27] and 2 b-4 b are fulleropyrrolidines that were prepared through the 1,3-dipolar cycloaddition of the azomethine ylide [28] that forms when each of the (E)-azoaromatic aldehydes 2 a-3 a and 6 is treated with N-(3,6,9-trioxadecyl)glycine [29] (or N-methylglycine in the case of dyad 1 d) in the presence of C 60 in refluxing chlorobenzene. Dyads 2 b www.chemeurj.org and 3 b were prepared in a single step from the corresponding azoaromatic aldehydes 2 a and 3 a in 40-45 % isolated yields (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Photophysics, and Photoresponse of Fullerene‐Based Azoaromatic Dyads

Possamai

Marcuz

Maggini

et al. 2005

Chemistry A European J

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The synthesis and photophysical characterization of a series of fullerene-based, donor-acceptor dyads is presented, along with a description of their behavior as single molecular components in photovoltaic cells. The spectroscopic and photophysical properties of the dyads, investigated by steady-state fluorescence spectroscopy, pico- and nanosecond transient optical spectroscopy and time-resolved electron paramagnetic resonance (EPR) spectroscopy, revealed that the dyads undergo multiple-step energy transfer from the donor singlet excited state to the fullerene triplet excited state, which in turn decays to the donor triplet state. The inefficient formation of a charge-separated state, both in solution and in the solid state, translates into a poor photovoltaic performance of dyads 2 b-4 b if compared to that of dyad 1 b, in which photoinduced electron transfer is operative in the solid state. In addition, the results of the photophysical investigation suggested that the performance of the solar cells was also limited by the low-lying donor triplet excited state that acts as a photoexcitation energy sink.

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Section: Resultsmentioning

confidence: 99%

“…white light illumination, for the fullerene-azothiophene dyad [26] 1 b. The significant absorption of the dyad in the visible spectral region (l max = 567 nm), coupled to the optimization of the active layer thickness, contributed to the photovoltaic performance of cells made of dyad 1 b.…”

Section: à2mentioning

confidence: 99%

Synthesis, Photophysics, and Photoresponse of Fullerene‐Based Azoaromatic Dyads

Possamai

Marcuz

Maggini

et al. 2005

Chemistry A European J

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“…47] Maggini et al synthesized a fullerene azothiophene dyad ( 7 ) and used it as the active material in a cell based on a fi lm spin-cast from chloroform solution sandwiched between ITO/PEDOT-PSS and aluminum electrodes. [ 48 ] Under 80 mW cm − 2 white-light illumination the device gave a V oc of 0.66 V, a J sc of 1.60 mA cm − 2 , and a FF of 0.28, leading to a PCE of 0.37%. A strong effect of fi lm thickness was observed with J sc decreasing from 1600 to 6 μ A cm − 2 when thickness increased from 45 to 105 nm.…”

Section: -Derivatized Linear π -Conjugated Systems: "Double Cablmentioning

confidence: 99%

Single Material Solar Cells: the Next Frontier for Organic Photovoltaics?

Roncali

2011

Advanced Energy Materials

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An overview of various approaches for the realization of single‐material organic solar cells (SMOCs) is presented. Fullerene‐conjugated systems dyads, di‐block copolymers, and self‐organized donor‐acceptor molecules all represent different possible approaches towards SMOCs. Although each of them presents specific advantages and poses specific problems of design and synthesis, these different routes have witnessed significant progress in the past few years and SMOCs with efficiencies in the range of 1.50% have been realized. These performances are already higher than those of bi‐component bulk heterojunction solar cells some ten years ago, demonstrating that SMOCs can represent a credible approach towards efficient and simple organic solar cells. Possible directions for future research are discussed with the aim of stimulating further research on this exciting topic.

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“…Actually, the molecular approach is not only an interesting model system of the devices by means of bulk heterojunction materials but it appears also as an excellent alternative to the polymeric approach. Indeed, the photosensitivity and the energy-conversion efficiency obtained with devices prepared with fullerene-(pconjugated oligomer) dyads capable of achieving efficient and very fast photoinduced charge separation are quite promising [4]. Furthermore, this new synthetic approach also offers great versatility for design tuning of the photovoltaic system.…”

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“…Subsequent treatment with CBr 4 /PPh 3 /Zn under the conditions described by CoreyÀFuchs [9] yielded dibromoolefine derivative 6 in a quantitative yield. Elimination of HBr and halogen-metal exchange was best achieved with an excess of LDA [15] in THF at À 788, and the resulting anion was quenched with NH 4 Cl to give mono-protected bis-alkyne derivative 7 in 91% yield. The OPE dimer 8 was then obtained in 79% yield by Pd-catalyzed cross-coupling between 4 and 7.…”

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A New Iterative Approach for the Synthesis of Oligo(phenyleneethynediyl) Derivatives and Its Application for the Preparation of FullereneOligo(phenyleneethynediyl) Conjugates as Active Photovoltaic Materials

Nierengarten¹,

Gu²,

Hadziioannou³

et al. 2004

Helvetica Chimica Acta

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Disymmetrically substituted oligo(phenyleneethynediyl) (OPE) derivatives were prepared from 2,5-bis(octyloxy)-4-[(triisopropylsilyl)ethynyl]benzaldehyde (5) by an iterative approach using the following reaction sequence: i) Corey ± Fuchs dibromoolefination, ii) treatment with an excess of lithium diisopropylamide, and iii) a metal-catalyzed cross-coupling reaction of the resulting terminal alkyne with 2,5-diiodo-1,4-bis(octyloxy)benzene (3) (Schemes 2 and 3). Reaction of the OPE dimer 8 and trimer 13 thus obtained with Nmethylglycine and C 60 in refluxing toluene gave the corresponding C 60 ÀOPE conjugates 16 and 17, respectively (Scheme 4). On the other hand, treatment of the protected terminal alkynes 8 and 13 with Bu 4 N followed by reaction of the resulting 9 and 14 with 4-iodo-N,N-dibutylaniline under Sonogashira conditions yielded 10 and 15, respectively (Schemes 2 and 3). Subsequent treatment with N-methylglycine and C 60 in refluxing toluene furnished the C 60 ÀOPE derivatives 18 and 19 (Scheme 4). Compound 9 was also subjected to a Pd-catalyzed cross-coupling reaction with 3 to give the centrosymmetrical OPE pentamer 20 (Scheme 5). Subsequent reduction followed by reaction of the resulting diol 21 with acid 22 under esterification conditions led to bismalonate 23. Oxidative coupling of terminal alkyne 14 with the Hay catalyst gave bis-aldehyde 24 (Scheme 6). Treatment with diisobutylaluminium hydride followed by dicylcohexylcarbodiimide-mediated esterification with acid 22 gave bis-malonate 26. Finally, treatment of bis-malonates 23 and 26 with C 60 , I 2 , and 1,8-diazabicylco[5.4.0]undec-7-ene (DBU) in toluene afforded the bis[cyclopropafullerenes] 27 and 28, respectively (Scheme 7). The C 60 derivatives 16 ± 19, 27, and 28 were tested as active materials in photovoltaic devices. Each C 60 ÀOPE conjugate was sandwiched between poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate)-covered indium tin oxide and aluminium electrodes. Interestingly, the performances of the devices prepared from the N,N-dialkylaniline-terminated derivatives 18 and 19 are significantly improved when compared to those obtained with 16, 17, 27, and 28, thus showing that the efficiency of the devices can be significantly improved by increasing the donor ability of the OPE moiety.

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Solar cells based on a fullerene–azothiophene dyad

Abstract: A power conversion efficiency of 0.37%, under white light of 80 mW cm-2 intensity, was obtained when a fullerene-azothiophene dyad was used as the active layer of a photovoltaic cell.

Cited by 47 publications

References 12 publications

Synthesis, Photophysics, and Photoresponse of Fullerene‐Based Azoaromatic Dyads

Synthesis, Photophysics, and Photoresponse of Fullerene‐Based Azoaromatic Dyads

Single Material Solar Cells: the Next Frontier for Organic Photovoltaics?

A New Iterative Approach for the Synthesis of Oligo(phenyleneethynediyl) Derivatives and Its Application for the Preparation of FullereneOligo(phenyleneethynediyl) Conjugates as Active Photovoltaic Materials

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