Diastereoselective syntheses and oxygenation of silyl fulleroids

Kabe, Yoshio; Hachiya, Houjin; Saito, Tomohisa; Shimizu, Daisuke; Ishiwata, Masakatsu; Suzuki, Kazuharu; Yakushigawa, Yuko; Andō, Wataru

doi:10.1016/j.jorganchem.2009.01.046

Cited by 11 publications

(8 citation statements)

References 112 publications

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“…Oxygenation of the silyl homofullerene was also observed to form the silyl enol ether 27 via 1,3-silyl migration of a diketone intermediate. [38] This is the first example of singlet oxygenation of a monohomofullerene.…”

Section: Oxidation With Singlet Oxygenmentioning

confidence: 90%

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Gan¹,

Yang²,

Zhang³

et al. 2010

Advanced Materials

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Open-cage fullerenes can act as hosts for small molecules such as water, nitrogen, or hydrogen, forming endohedral fullerenes. Following a brief summary of carbon, nitrogen, and oxygen insertion in the fullerene framework to form homofullerenes, methods of creating a hole in the fullerene surface are surveyed. Techniques of hole enlargement and the insertion of atoms or molecules through the orifice to form endohedral fullerenes are described. Finally, the possibility of subsequent closure of the hole is considered.

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Section: Oxidation With Singlet Oxygenmentioning

confidence: 90%

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Gan¹,

Yang²,

Zhang³

et al. 2010

Advanced Materials

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“…Most of the known methods employ singlet oxygen oxidation as a key step, which undergoes a 2 + 2 cycloaddition to form a dioxetane intermediate followed by ring-opening rearrangement to form fullerenediones. This process is well-established and successfully applied to the synthesis of a number of open-cage fullerene derivatives. − Opening of the fullerene cage results in remarkable change of the physical properties, such as their redox potentials. Recently, Murata and co-workers found that open-cage fullerenes can improve the open-circuit voltage of fullerene-based solar cells .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes

Yu¹,

Xie

Zhang

et al. 2011

J. Org. Chem.

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Oxidation of the fullerenediol C(60)(OH)(2)(O)(OAc)(OOtBu)(3) with PhI(OAc)(2) yields the open-cage fullerene derivative C(60)(O)(2)(O)(OAc)(OOtBu)(3)2 with an 11-membered orifice. Compound 2 reacts with aniline to form a new open-cage derivative with a 14-membered orifice, which yields an 18-membered open-cage fullerene derivative upon addition of another molecule of aniline. Two different types of aniline derivatives with either electron-donating or electron-withdrawing substituents can be added sequentially, affording an unsymmetrical moiety in the open-cage structure. Reduction potentials of the 18-membered open-cage fullerene derivatives can be fine-tuned by changing the substituents on the aniline. The results provide new insights about the mechanism of open-cage reactions of fullerene-mixed peroxide.

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“…Moreover, a suitable and efficient Pd(OAc) 2 -catalyzed Nheteroannulation transformation of [60]fullerene with benzoyl hydrazone esters was accomplished for the synthesis of novel Nunsubstituted 2-fulleropyrrolines (249). Under benign conditions, the self-sensitized photo-oxidation of 2-fulleropyrrolines was first designed to produce ketoamide fullerene adduct.…”

Section: Self-sensitized Photooxidation Of Fullerene Derivativesmentioning

confidence: 99%

“…The 1 O 2 self‐photooxidation of silyl fulleroids has also been studied (249). Specifically, the silyl fulleroids 82 having the silyl group above the five‐membered ring were self‐photooxygenated to afford the diketone intermediate 83 .…”

Section: C60‐sensitized Photooxygenationsmentioning

confidence: 99%

Singlet Oxygen: Discovery, Chemistry, C₆₀‐Sensitization^†

Orfanopoulos

2021

Photochem & Photobiology

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This review article refers to the discovery of excited molecular oxygen, in particular on its lower singlet excited state ( 1 D g , 1 O 2 ). After a short report on singlet oxygen generation, the review is focused on the chemistry of this reactive species. Specifically, the three major reactions of 1 O 2 with unsaturated organic substrates, namely the [4 + 2] and [2 +2] cycloadditions as well as the ene reaction, are reviewed. The proposed mechanisms of these reactions, through the years, based on experimental and computational work, have been presented. Selected examples of singlet oxygen-synthetic applications are also mentioned. The [60]fullerene and fullereno-materials photosensitized oxidations in homogeneous, as well as in heterogeneous conditions, are also comprehensively discussed.Finally, the self-sensitized photooxidation of open cage fullerenes as well as fullerenes bearing oxidizable groups is reported.

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Diastereoselective syntheses and oxygenation of silyl fulleroids

Cited by 11 publications

References 112 publications

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes

Singlet Oxygen: Discovery, Chemistry, C₆₀‐Sensitization^†

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Diastereoselective syntheses and oxygenation of silyl fulleroids

Cited by 11 publications

References 112 publications

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes

Singlet Oxygen: Discovery, Chemistry, C60‐Sensitization†

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Singlet Oxygen: Discovery, Chemistry, C₆₀‐Sensitization^†