Open Access

Chemical Science

, volume 11 , issue 2 , pages 384-388

Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns

Kai Qing Liu ^{1, 2, 3, 4, 5, 6}

Jun Jie Wang ^{1, 2, 3, 4, 5, 6}

Xing Xing Yan ^{1, 2, 3, 4, 5, 6}

Chuang Niu ^{1, 2, 3, 4, 5, 6}

Guan-Wu Wang ^{1, 2, 3, 4, 5, 6, 7}

Hide authors affiliations Show authors affiliations: 7 affiliations

Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Center for Excellence in Molecular Synthesis of CAS, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China |

Hefei National Laboratory for Physical Sciences at Microscale |

CAS Key Laboratory of Soft Matter Chemistry

⁴

iChEM (Collaborative Innovation Center of Chemistry for Energy Materials)

⁵

Center for Excellence in Molecular Synthesis of CAS

⁶

DEPARTMENT OF CHEMISTRY

⁷

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China |

Publication type: Journal Article

Publication date: 2020-01-01

Royal Society of Chemistry (RSC)

Chemical Science

scimago Q1

wos Q1

SJR: 2.138

CiteScore: 12.6

Impact factor: 7.4

ISSN: 20416520, 20416539

DOI: 10.1039/c9sc02131k

Copy DOI

PubMed ID: 32153753

General Chemistry

Abstract

The efficient and regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns has been achieved. The tetra-functionalized [60]fullerene derivative with an intriguing 1,2,4,17-addition pattern is regioselectively obtained by cyclization reaction of the dianionic species generated electrochemically from a [60]fulleroindoline with 1,2-bis(bromomethyl)benzene at 0 °C, and can be converted to the more stable 1,2,3,4-adduct at 25 °C. Furthermore, the hexa-functionalized [60]fullerene derivative with the 1,2,3,4,9,10-addition pattern displaying a unique “S”-shaped configuration can be synthesized by protonation of the electrochemically generated dianion of the obtained tetra-functionalized 1,2,4,17-adduct. The structures of the tetra- and hexa-functionalized products have been determined by spectroscopic data and single-crystal X-ray analysis.

Found

2 citations

Kraevaya Olga

🥼 🤝

PhD in Chemistry

74 publications, 475 citations, 12 reviews

h-index: 12

Federal Research Center of Problem of Chemical Physics and Medicinal Chemistry RAS

1 citation

Fujiki Michiya

65 publications, 1 391 citations, 168 reviews

h-index: 20

Nara Institute of Science and Technology

Research interests

Circularly polarized luminescence

Symmetry breaking

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GOST |

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Liu K. Q. et al. Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns // Chemical Science. 2020. Vol. 11. No. 2. pp. 384-388.

GOST all authors (up to 50) Copy

Liu K. Q., Wang J. J., Yan X. X., Niu C., Wang G. Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns // Chemical Science. 2020. Vol. 11. No. 2. pp. 384-388.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1039/c9sc02131k

UR - https://xlink.rsc.org/?DOI=C9SC02131K

TI - Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns

T2 - Chemical Science

AU - Liu, Kai Qing

AU - Wang, Jun Jie

AU - Yan, Xing Xing

AU - Niu, Chuang

AU - Wang, Guan-Wu

PY - 2020

DA - 2020/01/01

PB - Royal Society of Chemistry (RSC)

SP - 384-388

IS - 2

VL - 11

PMID - 32153753

SN - 2041-6520

SN - 2041-6539

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2020_Liu,

author = {Kai Qing Liu and Jun Jie Wang and Xing Xing Yan and Chuang Niu and Guan-Wu Wang},

title = {Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns},

journal = {Chemical Science},

year = {2020},

volume = {11},

publisher = {Royal Society of Chemistry (RSC)},

month = {jan},

url = {https://xlink.rsc.org/?DOI=C9SC02131K},

number = {2},

pages = {384--388},

doi = {10.1039/c9sc02131k}

}

MLA

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MLA Copy

Liu, Kai Qing, et al. “Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns.” Chemical Science, vol. 11, no. 2, Jan. 2020, pp. 384-388. https://xlink.rsc.org/?DOI=C9SC02131K.

Publisher

Royal Society of Chemistry (RSC)

Journal

Chemical Science

scimago Q1

wos Q1

SJR

2.138

CiteScore

12.6

Impact factor

7.4

ISSN

20416520 (Print)

20416539 (Electronic)