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Progress in Chemistry 2019, Vol. 31 Issue (6): 791-799 DOI: 10.7536/PC181040 Previous Articles   Next Articles

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: Online: Published:
  • 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)
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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
Fig. 1 Structures of organocatalysts in metal-free ATRP[59]
Fig. 2 Proposed mechanism for metal-free ATRP with 10-phenylphenothiazine(PTH) photocatalyst[39]
Fig. 3 Structures of phenothiazine catalysts studied in metal-free ATRP[60]
Fig. 4 Metal-free light-mediated ATRP using perylene as an organic photocatalyst[38]
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]
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]
Fig. 7 Proposed mechanism for metal-free photo-ATRP mediated by ?uorescein(FL) in the presence of tertiary-amine reducing agent[41]
Fig. 8 Proposed mechanism of photoinduced, metal-free ATRP using dye/amine initiating system[66]
Fig. 9 Proposed mechanism of photomediated ATRP with 4CzIPN organic molecules as catalysts[68]
Fig. 10 Proposed mechanism of photomediated ATRP with benzaldehydic organic molecules as catalysts[42]
Fig. 11 Photomediated flow reactors offer significant advantages to batch systems[82]
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]
Fig. 13 Flow setup for the synthesis of a semifluorinated block copolymer[86]
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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