Isomers of IC&lt;SUB&gt;70&lt;/SUB&gt;BA and Their Photovoltaic Performance in Polymer Solar Cells

Hu, Leihua; Cui, Rongli; Huang, Huan; Lin, Guoqing; Guo, Xihong; Yang, Shiling; Lian, Yongfu; Dong, Jinquan; Sun, Baoyun

doi:10.1166/jnn.2015.10022

Cited by 8 publications

(9 citation statements)

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“…It is noteworthy that there are a handful of other studies in the literature that reported on chromatographic separation of fullerene bisadduct isomers [ 8 , 12 – 14 ]. To the best of our knowledge, this is the first comprehensive analysis of IC 70 BA mixture using HPLC.…”

Section: Introductionmentioning

confidence: 99%

Separation and identification of indene–C₇₀ bisadduct isomers

Zhang¹,

Subbiah²,

Jones³

et al. 2016

Beilstein J. Org. Chem.

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SummaryFollowing an initial work on the isolation of a single geometric isomer from an indene–C70 bisadduct (IC70BA) mixture, we report the full fractionation and identification of the bisadduct species in the material. Eleven fractions of IC70BA isomers were separated by high-performance liquid chromatography. A number of fractions contained relatively pure isomer species and their configuration were deduced using a variety of analytical techniques including 1H and 13C NMR and UV–vis spectroscopy. The electrochemical properties and the organic solar cell device performance were investigated for fractions where a reasonable quantity of sample could be isolated.

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Section: Introductionmentioning

confidence: 99%

Separation and identification of indene–C₇₀ bisadduct isomers

Zhang¹,

Subbiah²,

Jones³

et al. 2016

Beilstein J. Org. Chem.

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“…The C 70 –indene bisadducts C 70 (C 9 H 8 ) 2 (C 70 ind 2 ; and often-abbreviated IC 70 BA) make up one of the presentable series of the regioisomeric C 70 derivatives. It should be noted that C 70 ind 2 had been used in photovoltaics as a mixture, ,, but their synthesis, separation, and separate testing in OSCs have been performed in a current work . Though this is an undoubted breakthrough in the field, the C 70 ind 2 regioisomers have been isolated as fractions containing one major isomer with admixtures of the minor ones.…”

Section: Resultsmentioning

confidence: 99%

The C₇₀ Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics

Sabirov

2016

J. Phys. Chem. C

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Currently, higher fullerene adducts (bis-, tris-, and multiadducts) come into use as electron acceptor components for organic solar cells (OSCs) with enhanced output parameters. These compounds have numerous positional isomers, and isomerism crucially influences the performances of photovoltaic devices. Indeed, application of the isolated and purified fullerene adducts (isomer-free fullerene-adduct OSCs) allows increasing power conversion efficiency (PCE) compared to the use of the isomeric mixtures. Previously, we have found that OSCs reveal higher PCE if they utilize the C 60 bisadducts with the lowest anisotropy of polarizability. To demonstrate a general nature of the found correlation in the present work, we have theoretically studied anisotropy of polarizability of the selected isomeric C 70 mono-, bis-, and higher adducts synthesized and separately tested as OSC electron acceptors in recent experimental works. We have found that, as in the case of C 60 , less-anisotropic C 70 derivatives reveal higher PCE of the corresponding photovoltaic devices. Thus, the correlation between anisotropy of polarizability of fullerene acceptors and power conversion efficiency of OSC based on them has a general nature (regardless of the fullerene type and nature of addends), and we can formulate the minimum anisotropy hypothesis: f ullerene adducts with low anisotropy of polarizability are more ef f icient as electron acceptor materials for organic solar cells than their highly anisotropic regioisomers. This conjecture is supported with congruence of relevant experimental and computational data with scarce exceptions and may be recommended as an auxiliary tool for the molecular design and screening of novel fullerene derivatives promising for organic solar cells. The reasons for the importance of polarizability (and its anisotropy) underlying this principle are discussed.

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“…Widely studied C 60 and C 70 fullerene derivatives, such as PC 61 BM (Phenyl C 61 butyric acid methyl ester) or PCBM‐like fullerenes,,,,,,, indene modified fullerenes,,,, and (di‐)hydronaphthyl modified fullerenes,,,, have been used in different device architectures. While there are many papers describing the effect of fullerene mono‐ and multi‐adducts on the performance of an organic solar cell (see refs ,.…”

Section: Introductionmentioning

confidence: 99%

“…,,,. Especially for C 70 derivatives only a small number of papers can be found in literature in which the electrochemical behavior of rather few isolated fullerene derivatives are described ,,,…”

Section: Introductionmentioning

confidence: 99%

Effect of the Type and Number of Organic Addends on Fullerene Acceptors for n‐Type Electronic Devices: Redox Properties and Energy Levels

et al. 2018

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Fullerenes are still among the best performing electron acceptor materials for electronic applications such as organic solar cells, organic-inorganic perovskite solar cells and transistors. We demonstrate that voltammetry is a very powerful tool for the determination of the redox potentials and thus the LUMO levels of various fullerene acceptor materials when identical conditions, i. e. same electrolyte, electrode material and potential standard, are used. The analyzed fullerene derivatives bear several types (indene, anthracene and 1,2-dimethoxymethano groups) and numbers (mono-, bis-and tris-adducts) of addends. Our systematical study enables a direct correlation of the values obtained for the individual fullerenes, and a linear relationship of the redox potential and the number of addends was found. The high lying LUMO levels of the bis-and trisadducts are favorable in terms of a high open circuit voltage in combination with polymer donors in bulk heterojunction solar cells. Considering only high LUMO values IC 60 TA and IC 70 TA are the most promising materials for organic solar cells revealing a high V OC . The bis-adducts of the fullerenes reveal LUMO levels that closely match the energy level of the widely used organometal trihalide CH 3 NH 3 PbI in perovskite solar cells.

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Isomers of IC<SUB>70</SUB>BA and Their Photovoltaic Performance in Polymer Solar Cells

Cited by 8 publications

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Separation and identification of indene–C₇₀ bisadduct isomers

Separation and identification of indene–C₇₀ bisadduct isomers

The C₇₀ Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics

Effect of the Type and Number of Organic Addends on Fullerene Acceptors for n‐Type Electronic Devices: Redox Properties and Energy Levels

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Isomers of IC<SUB>70</SUB>BA and Their Photovoltaic Performance in Polymer Solar Cells

Cited by 8 publications

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Separation and identification of indene–C70 bisadduct isomers

Separation and identification of indene–C70 bisadduct isomers

The C70 Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics

Effect of the Type and Number of Organic Addends on Fullerene Acceptors for n‐Type Electronic Devices: Redox Properties and Energy Levels

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Separation and identification of indene–C₇₀ bisadduct isomers

Separation and identification of indene–C₇₀ bisadduct isomers

The C₇₀ Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics