Synthesis of 2-Pyrenylphosphines via Phospho-Fries Rearrangement

doi:10.6023/cjoc202009056

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1153-1160.DOI: 10.6023/cjoc202009056 Previous Articles Next Articles

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磷杂Fries重排反应用于合成2-芘基膦化合物

兰新婵¹, 王丽丽¹^,^*(), 段征¹^,^*(), François Mathey¹

1 郑州大学化学学院绿色催化研究中心国际磷化学实验室河南省有机磷功能分子国际联合实验室郑州 450001

收稿日期:2020-09-28 修回日期:2020-11-03 发布日期:2020-11-12
通讯作者: 王丽丽, 段征
基金资助:
国家自然科学基金(21672193); 国家自然科学基金(21272218); 国家工信部(Z135060009002); 河南省博士后基金(001803004); 河南省科技攻关项目(202102310327); 高等学校学科创新引智计划(D20003); 郑州大学资助项目

Synthesis of 2-Pyrenylphosphines via Phospho-Fries Rearrangement

Xinchan Lan¹, Lili Wang¹^,^*(), Zheng Duan¹^,^*(), François Mathey¹

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

Received:2020-09-28 Revised:2020-11-03 Published:2020-11-12
Contact: Lili Wang, Zheng Duan
About author:
* Corresponding authors. E-mail: wanglili@zzu.edu.cn;
duanzheng@zzu.edu.cn
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, François Mathey. Synthesis of 2-Pyrenylphosphines via Phospho-Fries Rearrangement[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1153-1160.

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Fig. & Tab. 7

References 11

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Compound	λ_abs^a/nm	λ_ex/nm	λ_em^a/nm		τ^b/ns		Φ_f^c
1-Pyrenol	335, 347, 364, 384	280	385, 405, 428		14.0		0.38
1a	326, 342	280	378, 398, 418		25.1		0.23
1b	326, 342	280	379, 398, 418		23.8		0.19
1c	326, 342	280	378, 397, 417		27.0		0.23
1d	329, 345	280	380, 399, 419		16.9		0.23
Compound	λ_abs^a/nm	λ_ex/nm		λ_em^a/nm		τ^b/ns		Φ_f^c
1e	328, 344	280		379, 398, 462		24.8		0.16
2a	335, 351, 383, 405	280		411, 433, 456		9.1		0.39
2b	335, 350, 384, 405	280		385, 408, 431, 457		10.6		0.39
2c	335, 351, 387, 408	280		415,438, 463		9.1		0.40
2d	338, 354, 385, 407	280		397, 418, 439		7.8		0.004
2e	338, 355, 386, 409	280		386, 418, 439		2.0		0.10
4a	254, 342	310		471		7.7		0.04
4b	252, 348	330		461		2.7		0.11
4c	249, 345	310		463		3.4		0.13

Compound	λ_abs^a/nm	λ_ex/nm	λ_em^a/nm		τ^b/ns		Φ_f^c
1-Pyrenol	335, 347, 364, 384	280	385, 405, 428		14.0		0.38
1a	326, 342	280	378, 398, 418		25.1		0.23
1b	326, 342	280	379, 398, 418		23.8		0.19
1c	326, 342	280	378, 397, 417		27.0		0.23
1d	329, 345	280	380, 399, 419		16.9		0.23
Compound	λ_abs^a/nm	λ_ex/nm		λ_em^a/nm		τ^b/ns		Φ_f^c
1e	328, 344	280		379, 398, 462		24.8		0.16
2a	335, 351, 383, 405	280		411, 433, 456		9.1		0.39
2b	335, 350, 384, 405	280		385, 408, 431, 457		10.6		0.39
2c	335, 351, 387, 408	280		415,438, 463		9.1		0.40
2d	338, 354, 385, 407	280		397, 418, 439		7.8		0.004
2e	338, 355, 386, 409	280		386, 418, 439		2.0		0.10
4a	254, 342	310		471		7.7		0.04
4b	252, 348	330		461		2.7		0.11
4c	249, 345	310		463		3.4		0.13

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磷杂Fries重排反应用于合成2-芘基膦化合物

Synthesis of 2-Pyrenylphosphines via Phospho-Fries Rearrangement

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