Synthesis, X-ray Structure and Mass Spectrum of Cs-C60(CF3)6

Romanova, Natalia A.; Tamm, Nadezhda B.; Markov, Vitaliy Yu.; Goryunkov, Alexey A.; Sidorov, Lev N.; Troyanov, Sergey I.

doi:10.1016/j.mencom.2012.11.005

Cited by 9 publications

(17 citation statements)

References 14 publications

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“…By contrast, non‐SPP C 70 (CF 3 ) n are less prone to fragmentation and show intense signals of molecular ions (Figure b). Previously, enhanced fragmentation of the SPP isomers has reported for the trifluoromethyl derivatives of C 60 : C 60 (CF 3 ) 12 and C 60 (CF 3 ) 6 . An easy detachment of CF 3 group from SPP‐C 60 (CF 3 ) 6 was attributed to formation of a stable cyclopentadienyl anion C 60 (CF 3 ) 5 − (Figure e) .…”

Section: Resultsmentioning

confidence: 77%

“…The SPP arrangements are observed in the most thermodynamically favorable isomers of hexa‐adducts with medium size addends like Cl, Br, and CH 3 groups, but with more bulkier CF 3 groups they sometimes become slightly less preferable. For example, C s ‐C 60 (CF 3 ) 6 and the double SPP isomers of C 60 (CF 3 ) 12 are 14 and 33 kJ mol −1 higher in energy with respect to the most stable respective isomer, correspondingly, and form only as minor admixtures . However, in the highly trifluoromethylated C 70 , SPP motifs are among the most favorable (see Table S2 in the Supporting Information and Refs.…”

Section: Resultsmentioning

confidence: 81%

“…For example, C s -C 60 (CF 3 ) 6 and the double SPP isomerso fC 60 (CF 3 ) 12 are 14 and 33 kJ mol À1 higher in energy with respect to the most stable respective isomer,c orrespondingly,a nd form only as minor admixtures. [10,34,35] However,i n the highly trifluoromethylated C 70 ,S PP motifs are among the most favorable (see Table S2 in the Supporting Information and Refs. [16], [23]).…”

Section: Structural Characterizationmentioning

confidence: 99%

“…Previously,e nhanced fragmentation of the SPP isomersh as reported for the trifluoromethyl derivatives of C 60 :C 60 (CF 3 ) 12 [34] andC 60 (CF 3 ) 6 . [35] An easy detachment of CF 3 group from SPP-C 60 (CF 3 ) 6 wasa ttributed to formation of a stable cyclopentadienyl anion C 60 (CF 3 ) 5 À (Figure 4e). [35] Indeed, DFT estimateso ft he CÀCF 3 bond dissociation energies (BDE) in SPP-C 60 (CF 3 ) 6 À predicted much weaker binding of the inner CF 3 group compared with the others (0.9 vs. 1.8-2.0 eV).…”

Section: Ms Maldi Behavior and Stability Considerationsmentioning

confidence: 99%

“…[35] An easy detachment of CF 3 group from SPP-C 60 (CF 3 ) 6 wasa ttributed to formation of a stable cyclopentadienyl anion C 60 (CF 3 ) 5 À (Figure 4e). [35] Indeed, DFT estimateso ft he CÀCF 3 bond dissociation energies (BDE) in SPP-C 60 (CF 3 ) 6 À predicted much weaker binding of the inner CF 3 group compared with the others (0.9 vs. 1.8-2.0 eV). [35] Our present DFT estimations reveal the same trends in the BDEs in the highly trifluoromethylated C 70 compounds (Table S2 and Figure S7 in the SupportingI nformation).…”

Section: Ms Maldi Behavior and Stability Considerationsmentioning

confidence: 99%

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Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Kosaya

Rybalchenko

Lukonina

et al. 2018

Chemistry An Asian Journal

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We survey the structure and electronic properties of the family of higher trifluoromethylated C (CF ) molecules with n=14, 16, 18, and 20. Twenty-two available compounds, of which thirteen are newly obtained and characterized, demonstrate the broad diversity of π-system topologies, which enabled us to study the interplay between the CF addition pattern and the electronic properties. UV/Vis spectroscopic and cyclic voltammetric studies demonstrate the importance of the exact addition pattern rather than the plain number of addends. Of particular interest is the skew pentagonal pyramid (SPP) addition pattern, which enables formation of closed-shell cyclopentadienyl anions C (CF ) through CF detachment upon electron transfer. A detailed study of the process is presented for a SPP-C (CF ) where potentiostatic electrolysis at the second reduction potential gives C (CF ) oxidizable to a persistent C (CF ) radical. Together with the literature data for the lower C (CF ) compounds with n=2-12, the present results show good correlation between the experimental boundary level positions and the DFT predictions. The compounds turn out to be electron acceptor molecular semiconductors with experimental LUMO energies and HOMO-LUMO gaps within the ranges of -4.3 to -3.7 eV and 1.6 to 3.3 eV, respectively, depending on the shape of the conjugated fragments. The HOMO levels fall within the range of -5.6 to -6.9 eV and show linear correlation with the number of addends.

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Section: Resultsmentioning

confidence: 77%

Section: Resultsmentioning

confidence: 81%

Section: Structural Characterizationmentioning

confidence: 99%

Section: Ms Maldi Behavior and Stability Considerationsmentioning

confidence: 99%

Section: Ms Maldi Behavior and Stability Considerationsmentioning

confidence: 99%

See 3 more Smart Citations

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Kosaya

Rybalchenko

Lukonina

et al. 2018

Chemistry An Asian Journal

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Unstable Isomer of C₉₀ Fullerene Isolated as Chloro Derivatives, C₉₀(1)Cl_10/12

Chilingarov

Troyanov

2016

Chemistry An Asian Journal

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High-temperature chlorination of C90 -containing fullerene fraction resulted in the isolation and X-ray structural characterization of C90 (1)Cl10/12 , the first derivatives of a relatively unstable isomer D5h -C90 (1) with a nanotubular shape. In the crystal structure, three isomers of both C90 (1)Cl10 and C90 (1)Cl12 with similar chlorination patterns co-crystallize in the same crystallographic site. Thus, in contrast to the previous reports, D5h -C90 (1) is present, though with a low abundance, in the fullerene soot produced by arc-discharge method with undoped graphite rods.

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Fullerene as Photocatalyst: Visible-Light Induced Reaction of Perfluorinated α,ω-Diiodoalkanes with C₆₀

et al. 2017

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Solution phase photochemical reaction of fullerene with perfluorinated alkyldiiodides I-R-I can be efficiently initiated by visible range irradiation that targets solely the fullerene component. Photoinduced electron transfer from fullerene onto the diiodide component effects dissociative formation of alkyl radicals RI subsequently consumed by C to give the principal detectable radical intermediate CRI. Experimentally established second-order kinetics with respect to the fullerene concentration evidence that fullerene plays its two roles of photocatalyst and reactant in a decoupled fashion, which suggests its catalytic ability to be of potential use in more complex photochemical systems. The main final product of the photochemical transformation observed is the singly linked dimer of the intermediates, I-R-C-C-R-I. Side reactions of CRI with the environment lead to quenching of the unpaired electron density by ortho- or para- attachment of hydrogen or iodine. The outlined kinetic findings are discussed in detail.

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Synthesis, X-ray Structure and Mass Spectrum of Cs-C60(CF3)6

Cited by 9 publications

References 14 publications

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Unstable Isomer of C₉₀ Fullerene Isolated as Chloro Derivatives, C₉₀(1)Cl_10/12

Fullerene as Photocatalyst: Visible-Light Induced Reaction of Perfluorinated α,ω-Diiodoalkanes with C₆₀

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Synthesis, X-ray Structure and Mass Spectrum of Cs-C60(CF3)6

Cited by 9 publications

References 14 publications

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Unstable Isomer of C90 Fullerene Isolated as Chloro Derivatives, C90(1)Cl10/12

Fullerene as Photocatalyst: Visible-Light Induced Reaction of Perfluorinated α,ω-Diiodoalkanes with C60

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Product

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Unstable Isomer of C₉₀ Fullerene Isolated as Chloro Derivatives, C₉₀(1)Cl_10/12

Fullerene as Photocatalyst: Visible-Light Induced Reaction of Perfluorinated α,ω-Diiodoalkanes with C₆₀