Synthesis of C<sub>60</sub>(O)<sub>3</sub>: An Open-Cage Fullerene with a Ketolactone Moiety on the Orifice

Xin, Nana; Yang, Xiaobing; Zhou, Zishuo; Zhang, Jianxin; Zhang, Showxin; Gan, Liangbing

doi:10.1021/jo3026302

Cited by 26 publications

(6 citation statements)

References 49 publications

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“…The distance between the two flagpole hydrogen atoms is shorter in 2b (2.154 Å) than that in 3a (2.279 Å) because of the steric effect of the phenyl groups in 2b . The geometry of the fullerene‐fused 1,4‐diphenylcyclohexene ring in 2b is similar to those observed for the DA adducts of oxafulleroids C 60 O 3 18 and C 60 O 4 19…”

Section: Resultssupporting

confidence: 63%

Regioselective Diels–Alder Reactions Directed by Carbonyl Groups on the Rim of Open‐Cage Fullerene Derivatives

Zhang

et al. 2013

Eur J Org Chem

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A C60 fullerene open‐cage derivative with an 18‐membered orifice reacts with electron‐rich dienes on the rim of the orifice selectively. Both the mono and the bis adduct have been obtained in good yields by controlling the ratio of the reactants and the reaction time. Single‐crystal structures show a head‐to‐tail and back‐to‐back dimer for the mono adduct of 1,4‐diphenylbutadine and a head‐to‐tail polymeric chain for the bis adduct of 2,3‐dimethylbutadiene.

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Section: Resultssupporting

confidence: 63%

Regioselective Diels–Alder Reactions Directed by Carbonyl Groups on the Rim of Open‐Cage Fullerene Derivatives

Zhang

et al. 2013

Eur J Org Chem

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“…Epoxides with formula C 60 O 5 or C 60 O 6 have been observed elsewhere after 1-3 minutes of ozonolysis [66], but were short-lived. IR evidence of cage rupture was found for high degree of oxygenation [67]. The softer oxidation conditions employed in our work could also account for their nondetection.…”

Section: Identification Of Transformation Productssupporting

confidence: 50%

Transformation of C60 fullerene aggregates suspended and weathered under realistic environmental conditions

Sanchís

Aminot

Abad

et al. 2018

Carbon

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The occurrence, fate and behaviour of carbon nanomaterials in the aquatic environment are dominated by their functionalization, association with organic material and aggregation behaviour. In particular, the degradation of fullerene aggregates in the aquatic environment is a primary influence on their mobility, sorption potential and toxicity. However, the degradation and kinetics of water suspensions of fullerenes remain poorly understood. In the present work, first, an analytical method based on liquid chromatography and high-resolution mass spectrometry (LC-HRMS) for the determination of C 60 fullerene and their environmental transformation products was developed. Secondly, a series of C 60 fullerene water suspensions were degraded under relevant environmental conditions, controlling the salinity, the humic substances content, the pH and the sunlight irradiation. Up to ten transformation products were tentatively identified, including epoxides and dimers with two C 60 units linked via one or two adjacent furane-like rings. Fullerenols were not observed under these environmentally relevant conditions. The kinetics of generation of each transformation product were studied with and without simulated sunlight conditions. The ionic strength of the media, its pH and the humic substances content were observed to modulate the kinetics of generation.

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“…The distances between the two carbonyl oxygen atoms and the two carbon atoms are 2.581 and 2.636 Å, respectively. The DIB oxidation could be extended to analogous fullerene derivatives with a diol moiety to form open‐cage compounds such as 7 , 8 and 9 . Treatment of 1 with PPh 3 /I 2 gave the ketolactone compound 9 in one step.…”

Section: Peroxide‐mediated Cage Openingmentioning

confidence: 99%

Peroxide‐Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open‐Cage Fulleroid C₅₅O₅

Gan

2014

The Chemical Record

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Replacement of a pentagon in [60]fullerene with five oxygen atoms yields the open-cage compound C55O5 with five carbonyl groups on the rim of the orifice. Our attempts to synthesize such a target molecule starting from C60 have led us to prepare the fullerene-mixed peroxides such as C60(OO-t-Bu)6 with all the peroxo addends surrounding the same pentagon. Further investigations of the peroxide chemistry have generated various open-cage fullerene derivatives, including the carbon monoxide encapsulated endohedral compound CO@C59O6. This Personal Account mainly discusses peroxide-based processes resulting in selective cleavage of the fullerene skeleton bonds.

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Synthesis of C₆₀(O)₃: An Open-Cage Fullerene with a Ketolactone Moiety on the Orifice

Cited by 26 publications

References 49 publications

Regioselective Diels–Alder Reactions Directed by Carbonyl Groups on the Rim of Open‐Cage Fullerene Derivatives

Regioselective Diels–Alder Reactions Directed by Carbonyl Groups on the Rim of Open‐Cage Fullerene Derivatives

Transformation of C60 fullerene aggregates suspended and weathered under realistic environmental conditions

Peroxide‐Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open‐Cage Fulleroid C₅₅O₅

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Synthesis of C60(O)3: An Open-Cage Fullerene with a Ketolactone Moiety on the Orifice

Cited by 26 publications

References 49 publications

Regioselective Diels–Alder Reactions Directed by Carbonyl Groups on the Rim of Open‐Cage Fullerene Derivatives

Regioselective Diels–Alder Reactions Directed by Carbonyl Groups on the Rim of Open‐Cage Fullerene Derivatives

Transformation of C60 fullerene aggregates suspended and weathered under realistic environmental conditions

Peroxide‐Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open‐Cage Fulleroid C55O5

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Synthesis of C₆₀(O)₃: An Open-Cage Fullerene with a Ketolactone Moiety on the Orifice

Peroxide‐Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open‐Cage Fulleroid C₅₅O₅