Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates

Yu, Yun; Yang, Xiao‐Yu; Ueno, Hiroshi; Okada, Hiroshi; Shibuya, Hiromasa; Choi, Yeong Suk; Jin, Yong

doi:10.1021/acs.joc.9b00549

Cited by 10 publications

(1 citation statement)

References 62 publications

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“…In this type of fullerene chemistry, C 60 first formed the Fullerenyl cations, including fullerenyl radical cations and organofullerenyl cations, via KO t Bu or Cu(II) salts, which later were attacked by aryl boronic acids, affording symmetric or unsymmetric adducts. [27][28] Electrochemical functionalization of fullerenes as a novel and powerful synthetic protocol has been widely used in recent years due to its mild reaction conditions, high regioselectivity and good yield. As shown in Fig.…”

Section: The Cycloaddition Reactions Of Fullerenes Usually Include [2...mentioning

confidence: 99%

Exploring the Inner and Outer Spaces of Fullerenes

Chen

Niu

Zhuang³

et al. 2019

The Electrochemical Society Interface

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Fullerene is the first molecular form of the elemental carbon, and its discovery more than three decades ago substantially revolutionalized nanoscience. One of the most intriguing structural feature of fullerene is its hollow interior which forms a closed cage; such a sub-nanomater inner space offers unique opportunities to entrap atoms, ions, or clusters, affording endohedral fullerenes. Meanwhile, the spherical skeleton of fullerene consists of a conjugated π system, enabling the feasibility of exohedral functionalizations of fullerene to utilize its outer space. Herein, we present a brief overview on recent advance in both endohedral and exohedral functionalizations of fullerenes as well as their potential applications in versatile fields.

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Section: The Cycloaddition Reactions Of Fullerenes Usually Include [2...mentioning

confidence: 99%

Exploring the Inner and Outer Spaces of Fullerenes

Chen

Niu

Zhuang³

et al. 2019

The Electrochemical Society Interface

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Synthesis of n‐type [60]Fullerene Derivatives with Sterically Bulky tert‐Butyl Groups for Vacuum Deposition Processes

Shibuya

Choi

et al. 2022

Chemistry An Asian Journal

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[60]Fullerene derivatives with high thermal stability can be used for vacuum deposition under heating to fabricate thin films for organic electronic devices. Here, we investigated the thermal stability of [60]fullerene derivatives with various bulky substituents for thermal evaporation under vacuum by means of thermogravimetric analysis under reduced and normal pressure. We found sterically bulky groups such as tert‐butyl groups of [60]fullerene derivatives lowered the vacuum deposition temperature. Also, we performed isothermal thermogravimetric analysis to examine the long‐term thermal stability of the designed compounds under heating conditions. Furthermore, we investigated the UV‐Vis absorption patterns of the deposited films. Absorption in the blue wavelength range, which was attributed to intermolecular HOMO–LUMO transitions among the molecular orbitals of adjacent [60]fullerenes, was dramatically modified. These results were associated with the prevention of aggregation among neighboring [60]fullerene by the sterically bulky groups. This concept could contribute to expanding the use of evaporable [60]fullerene derivatives in organic thin‐film electronics research fields.

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Synthesis and Characterization of Ionic Li⁺@C₇₀ Endohedral Fullerene

Ueno,

Kitabatake,

Mabuchi

et al. 2023

Chemistry A European J

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Ion‐endohedral‐fullerene has attracted growing interest due to the unique electronic and structural characteristics arising from its distinctive ionic nature. Although there has been only one reported ion‐encapsulated fullerene, Li+@C60, a significant number of fundamental and applied studies have been conducted, making a substantial impact not only in chemistry and physics but also across various interdisciplinary research fields. Nevertheless, studies on ion‐endohedral fullerenes are still in their infancy due to the limitations in variety, and hence, it remains an open question how the size and symmetry of fullerene, as well as the motion and position of the encapsulated ion, affect their physical/chemical properties. Herein, we report the synthesis of lithium‐ion‐endohedral [70]fullerene (Li+@C70 X−, X=PF6− and TFSI−), a novel ionic endohedral fullerene. X‐ray crystallography confirmed the encapsulation of Li+ by C70 cage as well as its ion‐pair structure stabilized by external TFSI− counter anion. The encapsulated Li+ drastically lowered the orbital energy of the C70 cage by Coulomb interactions but did not affect the orbital energy gap and degeneracy. DFT studies were also performed, which supported the experimentally observed electronic effects caused by the encapsulated Li+.

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Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates

Cited by 10 publications

References 62 publications

Exploring the Inner and Outer Spaces of Fullerenes

Exploring the Inner and Outer Spaces of Fullerenes

Synthesis of n‐type [60]Fullerene Derivatives with Sterically Bulky tert‐Butyl Groups for Vacuum Deposition Processes

Synthesis and Characterization of Ionic Li⁺@C₇₀ Endohedral Fullerene

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Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates

Cited by 10 publications

References 62 publications

Exploring the Inner and Outer Spaces of Fullerenes

Exploring the Inner and Outer Spaces of Fullerenes

Synthesis of n‐type [60]Fullerene Derivatives with Sterically Bulky tert‐Butyl Groups for Vacuum Deposition Processes

Synthesis and Characterization of Ionic Li+@C70 Endohedral Fullerene

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Synthesis and Characterization of Ionic Li⁺@C₇₀ Endohedral Fullerene