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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 3: 1153 - 1160

DOI: https://doi.org/10.6023/cjoc202009056

ARTICLES

Synthesis of 2-Pyrenylphosphines via Phospho-Fries Rearrangement

  • Xinchan Lan ,
  • Lili Wang ,
  • Zheng Duan ,
  • Fran?ois Mathey
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  • 1 International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, International Phosphorus Laboratory, Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001
* Corresponding authors. E-mail: ;

Received date: 2020-09-28

  Revised date: 2020-11-03

  Online published: 2020-11-12

Supported by

National Natural Science Foundation of China(21672193); National Natural Science Foundation of China(21272218); Ministry of Industry and Information Technology(Z135060009002); Postdoctoral Research Grant in Henan Province(001803004); Key Scientific and Technological Project of Henan Province(202102310327); Programme of Introducing Talents of Discipline to Universities (111 project)(D20003); Zhengzhou University

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Abstract

The planarity and high fluorescence quantum yield of pyrene make it an important building block in organic optoelectronic material. But 2-pyrene based conjugated materials are less developed due to the intrinsic low reactivity of 2-position. A series of (1-hydroxy)-2-pyrenylphosphine derivatives were synthesized from pyrenyl phosphates via phospho-Fries rearrangement under mild conditions. The pyrenyl phosphate precursors could be easily obtained from the reaction of 1-pyrenol with H-phosphonates or phosphine chlorides. Several pyrenyl phosphates were converted into new pyrene fused 1,3-oxaphospholes from the further reactions with N-arylimide chlorides. This research provides not only a convenient method for the funcationalization of pyrene at 2-position but also new organophosphorus based π-conjugated molecules. The absorption and emission properties of these new pyrene fused molecules were studied.

Key words： Keywords phospho-Fries rearrangement; 2-pyrenylphosphine; 1,3-oxaphosphole; functionalization

Cite this article

Xinchan Lan , Lili Wang , Zheng Duan , Fran?ois Mathey . Synthesis of 2-Pyrenylphosphines via Phospho-Fries Rearrangement[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1153 -1160 . DOI: 10.6023/cjoc202009056

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