Monocyclopropanated fullerene derivatives with decreased electron affinity as promising electron acceptor materials for organic solar cells

Mumyatov, Alexander V.; Goryachev, A. A.; Prudnov, Fedor A.; Mukhacheva, O. A.; Sagdullina, Diana K.; Chernyak, Alexander V.; Troyanov, Sergey I.; Troshin, Pavel A.

doi:10.1016/j.synthmet.2020.116565

Cited by 8 publications

(9 citation statements)

References 66 publications

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“…[34][35][36][37][38][39] The introduction of alkoxy substituents in the phenyl moiety for adducts F1 and F3 not only reduces their electron affinity but also has a benecial effect on the performance characteristics of organic solar cells as compared to the reference PC 61 BM-based system. 40 Fullerene F4, as well as PC 61 BM, contains an ester group (propyl ester of 2thienylpropanoic acid) but with a longer solubilizing propyl radical. Moreover, instead of the phenyl group, the 2-thienyl substituent is attached to the cyclopropane fragment.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of the fullerene derivatives consists of the formation of the corresponding tosylhydrazones, which are then introduced into the Hummelen-Wudl reaction with C 60 . 42 The details of the synthesis and spectroscopic characteristics of the fullerene derivatives F1, F3 and F4 were reported previously, 40,43,44 whereas the data for the new compounds F2, F5 and F6 are given in the ESI. † It should be noted that all the studied fullerene derivatives were structurally characterized.…”

Section: Resultsmentioning

confidence: 99%

“…The X-ray single crystal structures of PC 61 BM, F1, F3 and F4 were published previously. 40,44,45 Herein, it was possible to grow single crystals of F2, F3, F5 and F6 suitable for X-ray diffraction analysis by slow evaporation of their chloroform solutions (details given in the ESI †). Thus, having a set of structurally characterized fullerene derivatives provided us with a unique opportunity to investigate possible relationships between the molecular structures of these compounds and the performance characteristics of PSCs using them as ETL materials.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

What defines the perovskite solar cell efficiency and stability: fullerene-based ETL structure or film morphology?

El-Naggar

Mumyatov

Emelianov

et al. 2023

Sustainable Energy Fuels

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

What defines the perovskite solar cell efficiency and stability: fullerene-based ETL structure or film morphology?

El-Naggar

Mumyatov

Emelianov

et al. 2023

Sustainable Energy Fuels

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“…Other fullerene derivatives were synthesized and purified as reported previously. [53][54][55][56][57] Thin Film Preparation and Aging Experiments: Fullerene derivatives PC 61 BM, PC 71 BM, or F1-F14 were dissolved in chloroform under stirring at 40 °C for 24 h to obtain solutions with the concentration of 15 mg mL −1 . The obtained transparent solutions were filtered through a paper syringe filter and spin-coated on the precleaned soda lime glass substrates (25 × 25 mm, Isolab GmbH) inside the nitrogen-filled glove box.…”

Section: Methodsmentioning

confidence: 99%

The Mechanism of the Photodimerization of [60]Fullerene Derivatives: It is Still a Charge Separation Followed by a Back Transfer!

Martynov

Mumyatov

Gutsev

et al. 2023

Adv Funct Materials

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Herein, we present a systematic study of the photochemical behavior of a set of fullerene compounds bearing various organic addends attached to the fullerene cage. It has been shown that the yield of photodimerization products strongly depends on the structure and electronic properties of the material, primarily the electron affinity (acceptor strength) of the modified fullerene core. This finding being inconsistent with the conventional [2+2]cycloaddition mechanism and pointed to an alternative pathway. This proposed pathway involves photoinduced charge separation followed by back charge transfer events leading to the efficient generation of triplet excitons, which are responsible for the formation of dimerized species. The light‐induced charge separation pathway was confirmed by electron spin resonance spectroscopy and was supported by theoretical calculations. The revealed mechanism allows one to control the photochemical behavior of the fullerene derivatives via rational structural engineering: some of the compounds were shown to be fully resistant to photodimerization, which makes them promising candidates in the development of stable organic photovoltaics. Furthermore, this approach could be used to suppress back charge transfer in donor‐acceptor blends and hinder the formation of triplet excitons which represents one a major energy loss channel in the current generation of organic solar cells.

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“…Methanofullerenes I , II, and IV were reported recently [ 60 , 61 ]. Compound III represents a well-known n-type material for organic solar cells abbreviated as PCBM [ 62 ].…”

Section: Methodsmentioning

confidence: 99%

Self-Organization of Fullerene Derivatives in Solutions and Biological Cells Studied by Pulsed Field Gradient NMR

Avilova

Chernyak

Soldatova

et al. 2022

IJMS

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Fullerene derivatives are of great interest in various fields of science and technology. Fullerene derivatives are known to have pronounced anticancer and antiviral activity. They have antibacterial properties. Their properties are largely determined by association processes. Understanding the nature and properties of associates in solvents of various types will make it possible to make significant progress in understanding the mechanisms of aggregation of molecules of fullerene derivatives in solutions. Thus, this work, aimed at studying the size and stability of associates, is relevant and promising for further research. The NMR method in a pulsed field gradient was used, which makes it possible to directly study the translational mobility of molecules. The sizes of individual molecules and associates were calculated based on the Stokes–Einstein model. The lifetime of associates was also estimated. The interaction of water-soluble C60 fullerene derivatives with erythrocytes was also evaluated. The values of self-diffusion coefficients and the lifetime of molecules of their compounds in cell membranes are obtained. It is concluded that the molecules of fullerene derivatives are fixed on the cell surface, and their forward movement is controlled by lateral diffusion.

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Monocyclopropanated fullerene derivatives with decreased electron affinity as promising electron acceptor materials for organic solar cells

Cited by 8 publications

References 66 publications

What defines the perovskite solar cell efficiency and stability: fullerene-based ETL structure or film morphology?

What defines the perovskite solar cell efficiency and stability: fullerene-based ETL structure or film morphology?

The Mechanism of the Photodimerization of [60]Fullerene Derivatives: It is Still a Charge Separation Followed by a Back Transfer!

Self-Organization of Fullerene Derivatives in Solutions and Biological Cells Studied by Pulsed Field Gradient NMR

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