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Kabachnik–Fields反应
Polymer Chemistry · 2013 ·Vol. 5 ·期 6 ·1857-1862 · IF 5.231

‘One pot’ synthesis of well-defined poly(aminophosphonate)s: time for the Kabachnik–Fields reaction on the stage of polymer chemistry

Yaling Zhang,Yuan Zhao,Bin Yang,Chongyu Zhu,Yen Wei,Lei Tao

A multicomponent reaction (MCR) has been carried out on the platform of controlled radical polymerization (CRP) to construct a ‘one pot’ MCR-CRP system for the facile preparation of well-defined functional polymers. In the current work, a novel ‘one pot’ system has been built through a combination of the Kabachnik–Fields (KF) reaction and reversible addition fragmentation chain transfer (RAFT) polymerization. Compared to a traditional stepwise method and polymer post-polymerization modification, this novel ‘one pot’ system exhibited distinct advantages to much more facilely and efficiently prepared well-defined poly(aminophosphonate)s (polyAPPs). A series of unique polyAPPs have also been successfully prepared through this KF–RAFT system, suggesting this novel method is a general and versatile approach to prepare well-defined organophosphorous polymers.

研究领域: 高分子化学 · 材料科学
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ULTRASONICS SONOCHEMISTRY · 2016 · IF 4.556

Ultrasonic-assisted Kabachnik-Fields reaction for rapid fabrication of AIE-active fluorescent organic nanoparticles

Zi Long,Meiying Liu,Ruming Jiang,Guangjiang Zeng,Qing Wan,Hongye Huang,Fengjie Deng,Yiqun Wan,Xiaoyong Zhang,Yen Wei

Aggregation-induced emission (AIE)-active fluorescent organic nanoparticles (FNPs) have been extensively explored for fluorescence “turn-on” bio-imaging applications with the unique advantages over conventional FNPs. Transformation of AIE-active molecules into FNPs can greatly expand their biomedical application potential. Here we reported a novel “one-pot” strategy for fabricating AIE-active FNPs through an ultrasonic-assisted, catalysts-free and solvent-free Kabachnik-Fields (KF) reaction for the first time. The KF reaction can be completed within 10   min to generate AIE-active PTH-CHO-PEI-DEP FNPs through mixing polyethylenimine and aldehyde group containing AIE dyes and diethyl phosphate. These PTH-CHO-PEI-DEP FNPs were confirmed by proton nuclear magnetic resonance ( 1 H NMR) spectroscopy, transmission electron microscopy (TEM) and fluorescence spectroscopy etc. The cell uptake behavior as well as cell viability of PTH-CHO-PEI-DEP FNPs was examined to evaluate their potential for biomedical application. We demonstrated that the amphiphilic α-aminophosphonate polymers could self-assemble into PTH-CHO-PEI-DEP FNPs in aqueous solution and showed excellent water dispersibility. TEM image shows the size of PTH-CHO-PEI-DEP FNPs is 100–200   nm. More importantly, the PTH-CHO-PEI-DEP FNPs emit strong green fluorescence and desirable biocompatibility, making them very suitable for biomedical applications. Finally, thus smart FNPs design together with their excellent performance will open a new avenue in the development of FNPs for following biological processes such as carcinogenesis.

研究领域: 材料科学 · 生物医学工程 · 化学
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RUSSIAN CHEMICAL BULLETIN · 2024 ·Vol. 73 ·期 9 ·2725-2729 · IF 1.7

A novel route for the synthesis of phosphonate-containing siloxanes by the catalyst-free Kabachnik—Fields reaction

Yang Zhihui,Wang Xiaochen,Wang Yuanrong,Yang Jinyun,Lu Haifeng

A new route for the synthesis of siloxanes containing substituents with the phosphonate and amino groups based on the catalyst-free Kabachnik—Fields reaction was developed. The synthesis was accomplished under mild conditions using 3-aminopropylsilanes, cyclic ketones, and diethyl phosphite as the starting materials to give the corresponding 1-(3-silylpropylamino)cycloalkylphosphonates in high yields.

研究领域: 有机化学 · 药物化学 · 材料化学 · 分子合成 · 功能材料
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Materials Science & Engineering C-Materials for Biological Applications · 2017 · IF 4.164

Microwave-assisted multicomponent reactions for rapid synthesis of AIE-active fluorescent polymeric nanoparticles by post-polymerization method

Qian-yong Cao,Ruming Jiang,Meiying Liu,Qing Wan,Dazhuang Xu,Jianwen Tian,Hongye Huang,Yuanqing Wen,Xiaoyong Zhang,Yen Wei

The development of simple and effective methods for synthesis of fluorescent polymeric nanoparticles (FPNs) with aggregation-induced emission (AIE) plays an important role for the biomedical applications of AIE-active FPNs. In present work, we developed a facile strategy for the fabrication of AIE-active FPNs by a post-polymerization method based on the microwave-assisted Kabachnik–Fields (KF) reaction, which can conjugate with poly(PEGMA-NH 2 ), AIE-active dye (TPE-CHO) and diethyl phosphate (DP) under microwave irradiation within 5   min. The characterization results confirm that PEGMA-TPE FPNs are successfully prepared through the microwave-assisted KF reaction. The resultant AIE-active FPNs show high water dispersity, intensive fluorescence and low cytotoxicity. These features make these AIE-active FPNs great potential for biomedical applications. Moreover, the microwave-assisted KF reaction is simple, fast, atom economy that should be a general strategy for the fabrication of various multifunctional AIE-active FPNs. We believe this work will open up a new avenue for the preparation of AIE-active functional materials with great potential for different applications.

研究领域: 材料科学 · 生物医学工程 · 化学
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