BF3•Et2O Promoted Dienone-Phenol Type Rearrangement to Synthesize Phosphepine with Aggregation Induced Luminescence (AIE) Effect

doi:10.6023/cjoc202204012

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2481-2487.DOI: 10.6023/cjoc202204012 Previous Articles Next Articles

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BF₃•Et₂O促进的双烯酮-酚重排合成具有聚集诱导发光(AIE)效应的磷杂七元环化合物

郭泽, 吴迪, 王丽丽^*(), 段征^*()

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:2022-04-06 修回日期:2022-05-01 发布日期:2022-05-17
通讯作者: 王丽丽, 段征
基金资助:
国家自然科学基金(22171245); 国家自然科学基金(22101262); 国家自然科学基金(21672193); 河南省科技攻关(202102310327); 郑州大学资助项目

BF₃•Et₂O Promoted Dienone-Phenol Type Rearrangement to Synthesize Phosphepine with Aggregation Induced Luminescence (AIE) Effect

Ze Guo, Di Wu, Lili Wang(), Zheng Duan()

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:2022-04-06 Revised:2022-05-01 Published:2022-05-17
Contact: Lili Wang, Zheng Duan
Supported by:
National Natural Science Foundation of China(22171245); National Natural Science Foundation of China(22101262); National Natural Science Foundation of China(21672193); Key Scientific and Technological Project of Henan Province(202102310327); Zhengzhou University

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Abstract

Very recently, phosphepines has emerged as a new luminogen. Further explorations of this new motif in optical materials have been hampered by the lack of general and practical methods for their synthesis and derivation. The rearrangement of dienones promoted by acid or base is widely used in the preparation of phenols. A series of phosphepines with aggregation induced luminescence (AIE) effect were synthesized by the dienone-phenol rearrangement reaction of spirodienone six-membered phosphacycles in the presence of BF₃•Et₂O.

Key words: dienone-phenol rearrangement, phosphepine, aggregation-induced emission (AIE), BF₃•Et₂O

Cite this article

Ze Guo, Di Wu, Lili Wang, Zheng Duan. BF₃•Et₂O Promoted Dienone-Phenol Type Rearrangement to Synthesize Phosphepine with Aggregation Induced Luminescence (AIE) Effect[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2481-2487.

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Fig. & Tab. 8

Scheme 1. Synthesis of phosphepines

Scheme 2. Spirocyclic dienone-phenol rearrangement reactions and their applications in the synthesis of phosphepines

Figure 1. Crystal structures of compounds 3a and 3d

Scheme 3. BF3-promoted dienone-phenol rearrangements for the synthesis of phosphepines

Scheme 4. Plausible mechanisms for the dienone-phenol rearrangements

Figure 2. UV-Vis absorption spectra (a) and fluorescence spectra (b) of 3a~3h in CH2Cl2 at room temperature

Compound	λ_abs/nm	λ_ex/nm	λ_em/nm
3a	315	250	390
3b	309	300	388
3c	308	260	390
3d	308	290	397
3e	313	260	402
3f	321	260	398
3g	314	260	390
3h	310	260	395

Table 1. Photophysical datas of 3a~3h

Figure 3. (a) Fluorescence emission spectra of compound 3h in different ratios of water/THF solution, and (b) fluorescence intensity versus water content

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BF₃•Et₂O促进的双烯酮-酚重排合成具有聚集诱导发光(AIE)效应的磷杂七元环化合物

BF₃•Et₂O Promoted Dienone-Phenol Type Rearrangement to Synthesize Phosphepine with Aggregation Induced Luminescence (AIE) Effect

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