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化学进展 2019, Vol. 31 Issue (6): 791-799 DOI: 10.7536/PC181040 前一篇   后一篇

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有机催化原子转移自由基聚合

李宁, 胡欣**(), 方亮, 寇佳慧, 倪亚茹, 陆春华**()   

  1. 南京工业大学 材料科学与工程学院 材料化学工程国家重点实验室 江苏先进无机功能复合材料协同创新中心 江苏先进生物与化学制造协同创新中心 南京 210009
  • 收稿日期:2018-11-01 出版日期:2019-06-15 发布日期:2019-04-26
  • 通讯作者: 胡欣, 陆春华
  • 基金资助:
    国家自然科学基金项目(21604037); 国家自然科学基金项目(51872138); 国家自然科学基金项目(51503098); 江苏省高等学校优势学科建设工程项目; 江苏省高校青蓝工程; 江苏省六大人才高峰项目(XCL-029)
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Organocatalyzed Atom Transfer Radical Polymerization

Ning Li, Xin Hu**(), Liang Fang, Jiahui Kou, Yaru Ni, Chunhua Lu**()   

  1. College of Materials Science and Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Jiangsu Collaborative Innovation Center for Advanced Inorganic Function Composites, Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM), Nanjing Tech University, Nanjing 210009, China
  • Received:2018-11-01 Online:2019-06-15 Published:2019-04-26
  • Contact: Xin Hu, Chunhua Lu
  • About author:
    ** E-mail: (Xin Hu);
    (Chunhua Lu)
  • Supported by:
    National Natural Science Foundation of China(21604037); National Natural Science Foundation of China(51872138); National Natural Science Foundation of China(51503098); Priority Academic Program Development of the Jiangsu Higher Education Institutions(PAPD); Qing Lan Project; Six Talent Peaks Project in Jiangsu Province(XCL-029)

过渡金属催化的原子转移自由基聚合(ATRP)是合成结构可控聚合物的重要方法之一,尽管一系列改进ATRP方法可将催化剂的浓度降至ppm级,但不可避免的金属残留仍然是制约ATRP应用的主要瓶颈。近年来,科学家提出并发展了有机催化原子转移自由基聚合(O-ATRP),从根本上规避了金属催化剂的使用与残留。本文对有机催化原子转移自由基聚合的概念、催化体系和聚合机理进行了介绍,同时综述了该新聚合方法在高分子合成与材料制备方面的应用。

关键词： 有机催化, 原子转移自由基聚合, 光诱导, 功能高分子

Atom transfer radical polymerization(ATRP) is one of the most robust and versatile tools for the synthesis of well-defined polymers. The traditional ATRP have to be conducted with high concentration of metal catalyst to compensate for the unavoidable radical termination reaction. A series of ATRP variants have been developed to reduce the metal catalyst concentration to 100 ppm or below. However, the contamination of the metal residue still remains. Organocatalyzed ATRP(O-ATRP) provides a green and reliable route to functionalized well-defined polymer without metal residue. The development of organic photoredox catalyst system is the key point of O-ATRP. This review highlights the recent progress in O-ATRP, including the various organic photoredox catalyst systems and polymerization mechanism. Moreover, the applications of O-ATRP in polymer synthesis are discussed.

Key words: organocatalyzed, atom transfer radical polymerization(ATRP), photoinduced, functional polymer
()
图1 无金属ATRP的有机催化剂结构式[59]
Fig. 1 Structures of organocatalysts in metal-free ATRP[59]
图2 10-苯基吩噻嗪作为催化剂的无金属ATRP[39]
Fig. 2 Proposed mechanism for metal-free ATRP with 10-phenylphenothiazine(PTH) photocatalyst[39]
图3 吩噻嗪衍生物结构式[60]
Fig. 3 Structures of phenothiazine catalysts studied in metal-free ATRP[60]
图4 二萘嵌苯催化的光诱导ATRP[38]
Fig. 4 Metal-free light-mediated ATRP using perylene as an organic photocatalyst[38]
图5 N-苯基取代基的5,10-二氢吩嗪催化剂结构 (1: 5,10-二对甲氧基苯-5,10-二氢吩嗪;2:5,10-二苯基-5,10-二氢吩嗪;3:5,10-二对三氟甲基苯-5,10-二氢吩嗪;4: 5,10-二对腈基苯-5,10-二氢吩嗪;5: 5,10-二(2-萘基)-5,10-二氢吩嗪;6: 5,10-二(1-萘基)-5,10-二氢吩嗪)以及催化ATRP聚合机理[64]
Fig. 5 PC development for O-ATRP(top and mid).A proposed mechanism for ATRP mediated by a PC via photoexcitation to 1PC*, intersystem crossing(ISC)to the triplet state 3PC*, ET to form the radical cation doublet 2PC·+, and back ET to regenerate PC(bottom) and reversibly terminate polymerization[64]
图6 10-苯基吩口恶嗪,5,10-二苯基二氢吩嗪和10-苯基吩噻嗪的几何重组能和还原电位以及吩口恶嗪衍生物的最大吸收波长以及消光系数[65]
Fig. 6 Geometric reorganization energies and reduction potentials(vs SCE) for 10-phenylphenoxazine, diphenyl dihydrophenazine, and 10-phenylphenothiazine(top). Extinction coefficients at λmax with the visible absorbance spectrum of functionalized phenoxazine(bottom)[65]
图7 荧光素催化的光诱导无金属ATRP[41]
Fig. 7 Proposed mechanism for metal-free photo-ATRP mediated by ?uorescein(FL) in the presence of tertiary-amine reducing agent[41]
图8 染料/胺体系引发光诱导无金属ATRP[66]
Fig. 8 Proposed mechanism of photoinduced, metal-free ATRP using dye/amine initiating system[66]
图9 光诱导4CzIPN催化ATRP机理[68]
Fig. 9 Proposed mechanism of photomediated ATRP with 4CzIPN organic molecules as catalysts[68]
图10 对茴香醛调控的光诱导ATRP机理[42]
Fig. 10 Proposed mechanism of photomediated ATRP with benzaldehydic organic molecules as catalysts[42]
图11 连续流光诱导O-ATRP装置示意图[82]
Fig. 11 Photomediated flow reactors offer significant advantages to batch systems[82]
图12 (a)表面引发无金属ATRP反应结构式;(b)表面引发无金属ATRP示意图;(c)聚合动力学[84]
Fig. 12 (a) Chemical scheme and conditions for metal-free ATRP using α-bromoisobutyrate-based initiator-functionalized silicon substrates.(b) Illustration of surface-initiated, metal-free ATRP.(c) Plot of brush height as a function of irradiation time using varied light intensities in the benchtop chamber[84]
图13 流动化学技术合成含氟嵌段共聚物[86]
Fig. 13 Flow setup for the synthesis of a semifluorinated block copolymer[86]
图14 无金属催化的ATRP原位制备Fe3O4@PMMA核@壳结构纳米杂化材料的合成路线[89]
Fig. 14 Schematic stepwise representation of the synthetic route to core/shell PMMA-capped Fe3O4 nanoparticles by metal-free ATRP based on PTH as photocatalyst[89]
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doi: 10.1021/acsami.7b01863     URL     pmid: 28345352
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摘要

有机催化原子转移自由基聚合