Chemical Communications

, volume 57 , issue 77 , pages 9886-9889

FeCl₃-promoted regioselective synthesis of BODIPY dimers through oxidative aromatic homocoupling reactions

Zhengxin Kang ^{1, 2}

Qing-Hua Wu ^{1, 3}

Qinghua Wu ^{2, 4}

Xing Guo ^{1, 2}

Long Wang ¹

Yin Ye ^{1, 2}

Changjiang Yu ^{1, 2}

Hua Wang ¹

Erhong Hao ^{1, 2}

Lijuan Jiao ^{1, 2}

Hide authors affiliations Show authors affiliations: 4 affiliations

Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, China |

Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, 241002, China |

School of Pharmacy, Anhui University of Chinese Medicine, Hefei, China |

⁴

School of Pharmacy, Anhui University of Chinese Medicine, Hefei, 230012, China |

Publication type: Journal Article

Publication date: 2021-08-25

Royal Society of Chemistry (RSC)

Chemical Communications

scimago Q1

wos Q2

SJR: 1.037

CiteScore: 7.4

Impact factor: 4.2

ISSN: 13597345, 1364548X

DOI: 10.1039/d1cc04098g

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PubMed ID: 34494065

Materials Chemistry

Metals and Alloys

Surfaces, Coatings and Films

General Chemistry

Ceramics and Composites

Electronic, Optical and Magnetic Materials

Catalysis

Abstract

The direct 3,3′-dimerization of BODIPYs lacking substituent groups in the 1,2,6, and 7 positions was developed by oxidative coupling with FeCl3. This regioselective dimerization was achieved for BODIPYs substituted only in the 5-position with Cl or aryl groups. Further functionalization of the 5,5′-dichloride dimer gave the corresponding pyrrole or 4-(2-aminoethyl)morpholine disubstituted dimers 2f and 2g, respectively. While dimer 2f exhibited intense NIR absorption/emission maxima at 773/827 nm in toluene, dimer 2g showed favorable lysosome-targeting NIR fluorescence in living cells.

Found

2 citations

Krasnovskaya Olga

53 publications, 883 citations, 10 reviews

h-index: 17

Lomonosov Moscow State University

1 citation

Beloglazkina Elena

DSc in Chemistry, professor

297 publications, 3 268 citations, 11 reviews

h-index: 29

Lomonosov Moscow State University

1 citation

Ksenofontov Alexander

🥼 🤝

PhD in Chemistry

104 publications, 1 120 citations, 54 reviews

h-index: 17

G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences

Research interests

Computational chemistry

Coordination Chemistry

1 citation

Kalyagin Aleksandr

PhD in Chemistry

12 publications, 295 citations

h-index: 8

G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences

1 citation

Berezin Mikhail

DSc in Chemistry, professor

159 publications, 1 634 citations

h-index: 19

G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences

Research interests

Porphyrins

Synthesis

1 citation

Antina Elena

DSc in Chemistry

207 publications, 2 277 citations

h-index: 22

G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences

1 citation

Kalinkina Valeria

3 publications, 20 citations

h-index: 3

G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences

Ivanovo State University of Chemistry and Technology

1 citation

Kuzmin Vladimir

393 publications, 2 915 citations

h-index: 27

Emanuel Institute of Biochemical Physics of the Russian Academy of Sciences

1 citation

Sherudillo Artem

🤝

7 publications, 7 citations

h-index: 2

G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences

Research interests

BODIPY

Fluorescence

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GOST |

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Kang Z. et al. FeCl3-promoted regioselective synthesis of BODIPY dimers through oxidative aromatic homocoupling reactions // Chemical Communications. 2021. Vol. 57. No. 77. pp. 9886-9889.

GOST all authors (up to 50) Copy

Kang Z., Wu Q., Wu Q., Guo X., Wang L., Ye Y., Yu C., Wang H., Hao E., Jiao L. FeCl3-promoted regioselective synthesis of BODIPY dimers through oxidative aromatic homocoupling reactions // Chemical Communications. 2021. Vol. 57. No. 77. pp. 9886-9889.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/d1cc04098g

UR - https://xlink.rsc.org/?DOI=D1CC04098G

TI - FeCl3-promoted regioselective synthesis of BODIPY dimers through oxidative aromatic homocoupling reactions

T2 - Chemical Communications

AU - Kang, Zhengxin

AU - Wu, Qing-Hua

AU - Wu, Qinghua

AU - Guo, Xing

AU - Wang, Long

AU - Ye, Yin

AU - Yu, Changjiang

AU - Wang, Hua

AU - Hao, Erhong

AU - Jiao, Lijuan

PY - 2021

DA - 2021/08/25

PB - Royal Society of Chemistry (RSC)

SP - 9886-9889

IS - 77

VL - 57

PMID - 34494065

SN - 1359-7345

SN - 1364-548X

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2021_Kang,

author = {Zhengxin Kang and Qing-Hua Wu and Qinghua Wu and Xing Guo and Long Wang and Yin Ye and Changjiang Yu and Hua Wang and Erhong Hao and Lijuan Jiao},

title = {FeCl3-promoted regioselective synthesis of BODIPY dimers through oxidative aromatic homocoupling reactions},

journal = {Chemical Communications},

year = {2021},

volume = {57},

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

month = {aug},

url = {https://xlink.rsc.org/?DOI=D1CC04098G},

number = {77},

pages = {9886--9889},

doi = {10.1039/d1cc04098g}

}

MLA

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MLA Copy

Kang, Zhengxin, et al. “FeCl3-promoted regioselective synthesis of BODIPY dimers through oxidative aromatic homocoupling reactions.” Chemical Communications, vol. 57, no. 77, Aug. 2021, pp. 9886-9889. https://xlink.rsc.org/?DOI=D1CC04098G.

Publisher

Royal Society of Chemistry (RSC)

Journal

Chemical Communications

scimago Q1

wos Q2

SJR

1.037

CiteScore

7.4

Impact factor

4.2

ISSN

13597345 (Print)

1364548X (Electronic)

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