Challenges and Recent Developments of Photoflow-Reversible Deactivation Radical Polymerization (RDRP)

Zhuo-Ran Zhong; Yi-Nan Chen; Yang Zhou; Mao Chen

doi:10.1007/s10118-021-2529-8

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Challenges and Recent Developments of Photoflow-Reversible Deactivation Radical Polymerization (RDRP)

FEATURE ARTICLE | Updated：2021-01-05

- Challenges and Recent Developments of Photoflow-Reversible Deactivation Radical Polymerization (RDRP)
- Challenges and Recent Developments of Photoflow-Reversible Deactivation Radical Polymerization (RDRP)
- Chinese Journal of Polymer Science 2021年39卷第9期页码：1069-1083
- Affiliations：
  
  State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, China
- Author bio：
  
  chenmao@fudan.edu.cn
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 21704016 and 21971044).
- DOI：10.1007/s10118-021-2529-8
  中图分类号：
- 收稿：2020-10-21，
  
  修回：2020-11-19，
  
  录用：2020-11-20，
  
  网络首发：2021-01-05，
  
  纸质出版：2021-07-18
- Accepted：
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Zhong, Z. R.; Chen, Y. N.; Zhou, Y.; Chen, M. Challenges and recent developments of photoflow-reversible deactivation radical polymerization (RDRP). Chinese J. Polym. Sci. 2021, 39, 1069–1083

Zhuo-Ran Zhong, Yi-Nan Chen, Yang Zhou, et al. Challenges and Recent Developments of Photoflow-Reversible Deactivation Radical Polymerization (RDRP)[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1069-1083.
Zhong, Z. R.; Chen, Y. N.; Zhou, Y.; Chen, M. Challenges and recent developments of photoflow-reversible deactivation radical polymerization (RDRP). Chinese J. Polym. Sci. 2021, 39, 1069–1083 DOI： 10.1007/s10118-021-2529-8.

Zhuo-Ran Zhong, Yi-Nan Chen, Yang Zhou, et al. Challenges and Recent Developments of Photoflow-Reversible Deactivation Radical Polymerization (RDRP)[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1069-1083. DOI： 10.1007/s10118-021-2529-8.

摘要

Abstract

Photo-controlled reversible-deactivation radical polymerization (photo-RDRP) has been investigated as a “green” and spatiotemporally controlling pathway for polymer synthesis. While the combination of photo-RDRP and flow chemistry has offered opportunities to increase light intensity and enable uniform light irradiation

problems associated with flow approaches still remain for photoflow-RDRP

which has hindered merging flow polymerization with other cutting-edge techniques. Herein

we summarize challenges and recent achievements in photoflow-RDRP including the development of (a) droplet/slug-flow to regulate residence time distribution

(b) mixing techniques to tailor polymer

and (d) computer-aided synthesis. We hope this work will provide informative knowledge to people in related fields and stimulate novel ideas to promote polymer synthesis in both academia and industry.

关键词

Keywords

references

Steinbacher, J. L.; McQuade, D. T. . Polymer chemistry in flow: new polymers, beads, capsules, and fibers . J. Polym. Sci., Part A: Polym. Chem. , 2006 . 44 6505 - 6533 . DOI: 10.1002/pola.21630 http://doi.org/10.1002/pola.21630 .

DeMello, A. J. . Control and detection of chemical reactions in microfluidic systems . Nature , 2006 . 442 394 - 402 . DOI: 10.1038/nature05062 http://doi.org/10.1038/nature05062 .

Geyer, K.; Codee, J. D.; Seeberger, P. H. . Microreactors as tools for synthetic chemists-the chemists' round-bottomed flask of the 21 st century? . Chem. Eur. J. , 2006 . 12 8434 - 8442 . DOI: 10.1002/chem.200600596 http://doi.org/10.1002/chem.200600596 .

Watts, P.; Wiles, C. . Recent advances in synthetic micro reaction technology . Chem. Commun. , 2007 . 443 - 467 . .

Voicu, D.; Scholl, C.; Li, W.; Jagadeesan, D.; Nasimova, I.; Greener, J.; Kumacheva, E. . Kinetics of multicomponent polymerization reaction studied in a microfluidic format . Macromolecules , 2012 . 45 4469 - 4475 . DOI: 10.1021/ma300444k http://doi.org/10.1021/ma300444k .

Knox, S. T.; Parkinson, S.; Stone, R.; Warren, N. J. . Benchtop flow-NMR for rapid online monitoring of RAFT and free radical polymerisation in batch and continuous reactors . Polym. Chem. , 2019 . 10 4774 - 4778 . DOI: 10.1039/C9PY00982E http://doi.org/10.1039/C9PY00982E .

Wilms, D.; Klos, J.; Frey, H. . Microstructured reactors for polymer synthesis: a renaissance of continuous flow processes for tailor-made macromolecules? . Macromol. Chem. Phys. , 2008 . 209 343 - 356 . DOI: 10.1002/macp.200700588 http://doi.org/10.1002/macp.200700588 .

Geacintov, C.; Smid, J.; Szwarc, M. . Kinetics of anionic polymerization of styrene in tetrahydrofuran . J. Am. Chem. Soc. , 1962 . 84 2508 - 2514 . DOI: 10.1021/ja00872a012 http://doi.org/10.1021/ja00872a012 .

Matyjaszewski, K., Comparison and classification of controlled/living radical polymerizations. In Controlled/living radical polymerization , American Chemical Society, Washington, DC, 2000 , Vol. 768, pp 2−26.

Braunecker, W. A.; Matyjaszewski, K. . Controlled/living radical polymerization: features, developments, and perspectives . Prog. Polym. Sci. , 2007 . 32 93 - 146 . DOI: 10.1016/j.progpolymsci.2006.11.002 http://doi.org/10.1016/j.progpolymsci.2006.11.002 .

Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P. T.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. . Living free-radical polymerization by reversible addition-fragmentation chain transfer: the RAFT process . Macromolecules , 1998 . 31 5559 - 5562 . DOI: 10.1021/ma9804951 http://doi.org/10.1021/ma9804951 .

Wang, J. S.; Matyjaszewski, K. . Controlled living radical polymerization—atom-transfer radical polymerization in the presence of transition-metal complexes . J. Am. Chem. Soc. , 1995 . 117 5614 - 5615 . DOI: 10.1021/ja00125a035 http://doi.org/10.1021/ja00125a035 .

Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. . Polymerization of methyl-methacrylate with the carbon-tetrachloride dichlorotris(triphenylphosphine)ruthenium(ii) methylaluminum bis(2,6-di- tert -butylphenoxide) initiating system-possibility of living radical polymerization . Macromolecules , 1995 . 28 1721 - 1723 . DOI: 10.1021/ma00109a056 http://doi.org/10.1021/ma00109a056 .

Hawker, C. J.; Bosman, A. W.; Harth, E. . New polymer synthesis by nitroxide mediated living radical polymerizations . Chem. Rev. , 2001 . 101 3661 - 3688 . DOI: 10.1021/cr990119u http://doi.org/10.1021/cr990119u .

Yagci, Y.; Jockusch, S.; Turro, N. J. . Photoinitiated polymerization: advances, challenges, and opportunities . Macromolecules , 2010 . 43 6245 - 6260 . DOI: 10.1021/ma1007545 http://doi.org/10.1021/ma1007545 .

Tehfe, M. A.; Louradour, F.; Lalevee, J.; Fouassier, J. P. . Photopolymerization reactions: on the way to a green and sustainable chemistry . Appl. Sci. , 2013 . 3 490 - 514 . DOI: 10.3390/app3020490 http://doi.org/10.3390/app3020490 .

Yamago, S.; Nakamura, Y. . Recent progress in the use of photoirradiation in living radical polymerization . Polymer , 2013 . 54 981 - 994 . DOI: 10.1016/j.polymer.2012.11.046 http://doi.org/10.1016/j.polymer.2012.11.046 .

Gong, H.; Ma, M.; Zhou, Y.; Zhao, Y.; Gu, Y.; Chen, M. . Photoredox controlled living polymerization . J. Funct. Polym. , 2019 . 32 271 - 291 . .

Shen, L. L.; Lu, Q. Z.; Zhu, A. Q.; Lv, X. Q.; An, Z. S. . Photocontrolled RAFT polymerization mediated by a supramolecular catalyst . ACS Macro Lett. , 2017 . 6 625 - 631 . DOI: 10.1021/acsmacrolett.7b00343 http://doi.org/10.1021/acsmacrolett.7b00343 .

Yang, Y. Q.; An, Z. S. . Visible light induced aqueous RAFT polymerization using a supramolecular perylene diimide/cucurbit 7 uril complex . Polym. Chem. , 2019 . 10 2801 - 2811 . DOI: 10.1039/C9PY00393B http://doi.org/10.1039/C9PY00393B .

Li, S. Z.; Han, G.; Zhang, W. Q. . Photoregulated reversible addition-fragmentation chain transfer (RAFT) polymerization . Polym. Chem. , 2020 . 11 1830 - 1844 . DOI: 10.1039/D0PY00054J http://doi.org/10.1039/D0PY00054J .

Corrigan, N.; Almasri, A.; Taillades, W.; Xu, J.; Boyer, C. . Controlling molecular weight distributions through photoinduced flow polymerization . Macromolecules , 2017 . 50 8438 - 8448 . DOI: 10.1021/acs.macromol.7b01890 http://doi.org/10.1021/acs.macromol.7b01890 .

Pan, X. C.; Tasdelen, M. A.; Laun, J.; Junkers, T.; Yagci, Y.; Matyjaszewski, K. . Photomediated controlled radical polymerization . Prog. Polym. Sci. , 2016 . 62 73 - 125 . DOI: 10.1016/j.progpolymsci.2016.06.005 http://doi.org/10.1016/j.progpolymsci.2016.06.005 .

Cambie, D.; Bottecchia, C.; Straathof, N. J.; Hessel, V.; Noel, T. . Applications of continuous-flow photochemistry in organic synthesis, material science, and water treatment . Chem. Rev. , 2016 . 116 10276 - 10341 . DOI: 10.1021/acs.chemrev.5b00707 http://doi.org/10.1021/acs.chemrev.5b00707 .

Nie, H. J.; Li, S. Z.; Qian, S. J.; Han, Z. Q.; Zhang, W. Q. . Switchable reversible addition-fragmentation chain transfer (RAFT) polymerization with the assistance of azobenzenes . Angew. Chem. Int. Ed. , 2019 . 58 11449 - 11453 . DOI: 10.1002/anie.201904991 http://doi.org/10.1002/anie.201904991 .

Zhang, Y. X.; He, J.; Dai, X. C.; Yu, L. L.; Tan, J. B.; Zhang, L. . Combining the power of heat and light: temperature-programmed photoinitiated RAFT dispersion polymerization to tune polymerization-induced self-assembly . Polym. Chem. , 2019 . 10 3902 - 3911 . DOI: 10.1039/C9PY00534J http://doi.org/10.1039/C9PY00534J .

Shanmugam, S.; Xu, J. T.; Boyer, C. . A logic gate for external regulation of photopolymerization . Polym. Chem. , 2016 . 7 6437 - 6449 . DOI: 10.1039/C6PY01361A http://doi.org/10.1039/C6PY01361A .

Chen, M.; Deng, S.; Gu, Y.; Lin, J.; MacLeod, M. J.; Johnson, J. A. . Logic-controlled radical polymerization with heat and light: multiple-stimuli switching of polymer chain growth via a recyclable, thermally responsive gel photoredox catalyst . J. Am. Chem. Soc. , 2017 . 139 2257 - 2266 . DOI: 10.1021/jacs.6b10345 http://doi.org/10.1021/jacs.6b10345 .

Wu, C.; Chen, H.; Corrigan, N.; Jung, K.; Kan, X.; Li, Z.; Liu, W.; Xu, J.; Boyer, C. . Computer-guided discovery of a pH-responsive organic photocatalyst and application for pH and light dual-gated polymerization . J. Am. Chem. Soc. , 2019 . 141 8207 - 8220 . DOI: 10.1021/jacs.9b01096 http://doi.org/10.1021/jacs.9b01096 .

Anastasaki, A.; Nikolaou, V.; Pappas, G. S.; Zhang, Q.; Wan, C.; Wilson, P.; Davis, T. P.; Whittaker, M. R.; Haddleton, D. M. . Photoinduced sequence-control via one pot living radical polymerization of acrylates . Chem. Sci. , 2014 . 5 3536 - 3542 . DOI: 10.1039/C4SC01374C http://doi.org/10.1039/C4SC01374C .

Tanaka, J.; Hakkinen, S.; Boeck, P. T.; Cong, Y.; Perrier, S.; Sheiko, S. S.; You, W. . Orthogonal cationic and radical RAFT polymerizations to prepare bottlebrush polymers . Angew. Chem. Int. Ed. , 2020 . 59 7203 - 7208 . DOI: 10.1002/anie.202000700 http://doi.org/10.1002/anie.202000700 .

Zhao, Y.; Ma, M.; Lin, X.; Chen, M. . Photoorganocatalyzed divergent reversible-deactivation radical polymerization towards linear and branched fluoropolymers . Angew. Chem. Int. Ed. , 2020 . 59 21470 - 21474 . DOI: 10.1002/anie.202009475 http://doi.org/10.1002/anie.202009475 .

Han, S.; Gu, Y.; Ma, M.; Chen, M. . Light-intensity switch enabled nonsynchronous growth of fluorinated raspberry-like nanoparticles . Chem. Sci. , 2020 . 11 10431 - 10436 . DOI: 10.1039/D0SC04141F http://doi.org/10.1039/D0SC04141F .

Sebra, R. P.; Reddy, S. K.; Masters, K. S.; Bowman, C. N.; Anseth, K. S. . Controlled polymerization chemistry to graft architectures that influence cell-material interactions . Acta Biomater. , 2007 . 3 151 - 161 . DOI: 10.1016/j.actbio.2006.07.010 http://doi.org/10.1016/j.actbio.2006.07.010 .

Jiang, K. M.; Han, S. T.; Ma, M. Y.; Zhang, L.; Zhao, Y. C.; Chen, M. . Photoorganocatalyzed reversible-deactivation alternating copolymerization of chlorotrifluoroethylene and vinyl ethers under ambient conditions: facile access to main-chain fluorinated copolymers . J. Am. Chem. Soc. , 2020 . 142 7108 - 7115 . DOI: 10.1021/jacs.0c01016 http://doi.org/10.1021/jacs.0c01016 .

Bai, H. D.; Huang, Z. H.; Yang, W. T. . Visible light-induced living surface grafting polymerization for the potential biological applications . J. Polym. Sci., Part A: Polym. Chem. , 2009 . 47 6852 - 6862 . DOI: 10.1002/pola.23724 http://doi.org/10.1002/pola.23724 .

Li, A.; Ramakrishna, S. N.; Nalam, P. C.; Benetti, E. M.; Spencer, N. D. . Stratified polymer grafts: synthesis and characterization of layered ‘brush’ and ‘gel’ structures . Adv. Mater. Interfaces , 2014 . 1 1300007 DOI: 10.1002/admi.201300007 http://doi.org/10.1002/admi.201300007 .

Zhang, Z.; Corrigan, N.; Bagheri, A.; Jin, J.; Boyer, C. . A versatile 3D and 4D printing system through photocontrolled RAFT polymerization . Angew. Chem. Int. Ed. , 2019 . 58 17954 - 17963 . DOI: 10.1002/anie.201912608 http://doi.org/10.1002/anie.201912608 .

Quan, Q.; Wen, H.; Han, S.; Wang, Z.; Shao, Z.; Chen, M. . Fluorous-core nanoparticle-embedded hydrogel synthesized via tandem photo-controlled radical polymerization: facilitating the separation of perfluorinated alkyl substances from water . ACS Appl. Mater. Interfaces , 2020 . 12 24319 - 24327 . DOI: 10.1021/acsami.0c04646 http://doi.org/10.1021/acsami.0c04646 .

Su, Y.; Straathof, N. J.; Hessel, V.; Noel, T. . Photochemical transformations accelerated in continuous-flow reactors: basic concepts and applications . Chem. Eur. J. , 2014 . 20 10562 - 10589 . DOI: 10.1002/chem.201400283 http://doi.org/10.1002/chem.201400283 .

Junkers, T.; Wenn, B. . Continuous photoflow synthesis of precision polymers . React. Chem. Eng. , 2016 . 1 60 - 64 . DOI: 10.1039/C5RE00042D http://doi.org/10.1039/C5RE00042D .

Tonhauser, C.; Nataello, A.; Lowe, H.; Frey, H. . Microflow technology in polymer synthesis . Macromolecules , 2012 . 45 9551 - 9570 . DOI: 10.1021/ma301671x http://doi.org/10.1021/ma301671x .

Diehl, C.; Laurino, P.; Azzouz, N.; Seeberger, P. H. . Accelerated continuous flow RAFT polymerization . Macromolecules , 2010 . 43 10311 - 10314 . DOI: 10.1021/ma1025253 http://doi.org/10.1021/ma1025253 .

Zaquen, N.; Kadir, A. M. N. B. P. H. A.; Iasa, A.; Corrigan, N.; Junkers, T.; Zetterlund, P. B.; Boyer, C. . Rapid oxygen tolerant aqueous RAFT photopolymerization in continuous flow reactors . Macromolecules , 2019 . 52 1609 - 1619 . DOI: 10.1021/acs.macromol.8b02628 http://doi.org/10.1021/acs.macromol.8b02628 .

Rubens, M.; Latsrisaeng, P.; Junkers, T. . Visible light-induced iniferter polymerization of methacrylates enhanced by continuous flow . Polym. Chem. , 2017 . 8 6496 - 6505 . DOI: 10.1039/C7PY01157A http://doi.org/10.1039/C7PY01157A .

Huang, W.; Zhai, J.; Hu, X.; Duan, J.; Fang, Z.; Zhu, N.; Guo, K. . Continuous flow photoinduced phenothiazine derivatives catalyzed atom transfer radical polymerization . Eur. Polym. J. , 2020 . 126 109565 DOI: 10.1016/j.eurpolymj.2020.109565 http://doi.org/10.1016/j.eurpolymj.2020.109565 .

Marathianos, A.; Liarou, E.; Anastasaki, A.; Whitfield, R.; Laurel, M.; Wemyss, A. M.; Haddleton, D. M. . Photo-induced copper-RDRP in continuous flow without external deoxygenation . Polym. Chem. , 2019 . 10 4402 - 4406 . DOI: 10.1039/C9PY00945K http://doi.org/10.1039/C9PY00945K .

Buss, B. L.; Miyake, G. M. . Photoinduced controlled radical polymerizations performed in flow: methods, products, and opportunities . Chem. Mater. , 2018 . 30 3931 - 3942 . DOI: 10.1021/acs.chemmater.8b01359 http://doi.org/10.1021/acs.chemmater.8b01359 .

Reis, M. H.; Leibfarth, F. A.; Pitet, L. M. . Polymerizations in continuous flow: recent advances in the synthesis of diverse polymeric materials . ACS Macro Lett. , 2020 . 9 123 - 133 . DOI: 10.1021/acsmacrolett.9b00933 http://doi.org/10.1021/acsmacrolett.9b00933 .

Zhu, N.; Hu, X.; Fang, Z.; Guo, K. . Continuous flow photoinduced reversible deactivation radical polymerization . ChemPhotoChem , 2018 . 2 831 - 838 . DOI: 10.1002/cptc.201800032 http://doi.org/10.1002/cptc.201800032 .

Bally, F.; Serra, C. A.; Hessel, V.; Hadziioannou, G. . Micromixer-assisted polymerization processes . Chem. Eng. Sci. , 2011 . 66 1449 - 1462 . DOI: 10.1016/j.ces.2010.07.026 http://doi.org/10.1016/j.ces.2010.07.026 .

Hornung, C. H.; Guerrero-Sanchez, C.; Brasholz, M.; Saubern, S.; Chiefari, J.; Moad, G.; Rizzardo, E.; Thang, S. H. . Controlled RAFT polymerization in a continuous flow microreactor . Org. Process. Res. Dev. , 2011 . 15 593 - 601 . DOI: 10.1021/op1003314 http://doi.org/10.1021/op1003314 .

Parida, D.; Serra, C.; Gómez, R.; Garg, D.; Hoarau, Y.; Bouquey, M.; Muller, R.; Ibarra-Gómez, R.; Bouquey, M.; Muller, R. . Atom transfer radical polymerization in continuous microflow: effect of process parameters . J. Flow. Chem. , 2014 . 4 92 - 96 . DOI: 10.1556/JFC-D-14-00003 http://doi.org/10.1556/JFC-D-14-00003 .

Muller, M.; Cunningham, M. F.; Hutchinson, R. A. . Continuous atom transfer radical polymerization in a tubular reactor . Macromol. React. Eng. , 2008 . 2 31 - 36 . DOI: 10.1002/mren.200700029 http://doi.org/10.1002/mren.200700029 .

Taylor, G. . Dispersion of soluble matter in solvent flowing slowly through a tube . Proc. Math. Phys. Eng. Sci. , 1997 . 219 186 - 203 . .

Russum, J. P.; Jones, C. W.; Schork, F. J. . Impact of flow regime on polydispersity in tubular RAFT miniemulsion polymerization . AlChE J. , 2006 . 52 1566 - 1576 . DOI: 10.1002/aic.10730 http://doi.org/10.1002/aic.10730 .

Hu, X.; Zhu, N.; Fang, Z.; Guo, K. . Continuous flow ring-opening polymerizations . React. Chem. Eng. , 2017 . 2 20 - 26 . DOI: 10.1039/c6re00206d http://doi.org/10.1039/c6re00206d .

Danckwerts, P. V. Continuous flow systems. . Continuous flow systems. Distribution of residence times . Chem. Eng. Sci. , 1995 . 50 3855 DOI: 10.1016/0009-2509(96)81810-0 http://doi.org/10.1016/0009-2509(96)81810-0 .

Reis, M. H.; Varner, T. P.; Leibfarth, F. A. . The influence of residence time distribution on continuous-flow polymerization . Macromolecules , 2019 . 52 3551 - 3557 . DOI: 10.1021/acs.macromol.9b00454 http://doi.org/10.1021/acs.macromol.9b00454 .

Song, Y.; Song, J.; Shang, M.; Xu, W.; Liu, S.; Wang, B.; Lu, Q.; Su, Y. . Hydrodynamics and mass transfer performance during the chemical oxidative polymerization of aniline in microreactors . Chem. Eng. J. , 2018 . 353 769 - 780 . DOI: 10.1016/j.cej.2018.07.166 http://doi.org/10.1016/j.cej.2018.07.166 .

Tumarkin, E.; Kumacheva, E. . Microfluidic generation of microgels from synthetic and natural polymers . Chem. Soc. Rev. , 2009 . 38 2161 - 2168 . DOI: 10.1039/b809915b http://doi.org/10.1039/b809915b .

Xu, S. Q.; Nie, Z. H.; Seo, M.; Lewis, P.; Kumacheva, E.; Stone, H. A.; Garstecki, P.; Weibel, D. B.; Gitlin, I.; Whitesides, G. M. . Generation of monodisperse particles by using microfluidics: control over size, shape, and composition . Angew. Chem. Int. Ed. , 2005 . 44 724 - 728 . DOI: 10.1002/anie.200462226 http://doi.org/10.1002/anie.200462226 .

Daniloska, V.; Tomovska, R.; Asua, J. M. . Designing tubular reactors to avoid clogging in high solids miniemulsion photopolymerization . Chem. Eng. J. , 2013 . 222 136 - 141 . DOI: 10.1016/j.cej.2013.02.015 http://doi.org/10.1016/j.cej.2013.02.015 .

Liu, Z.; Lu, Y.; Yang, B.; Luo, G. . Controllable preparation of poly(butyl acrylate) by suspension polymerization in a coaxial capillary microreactor . Ind. Eng. Chem. Res. , 2011 . 50 11853 - 11862 . DOI: 10.1021/ie201497b http://doi.org/10.1021/ie201497b .

Corrigan, N.; Manahan, R.; Lew, Z. T.; Yeow, J.; Xu, J. T.; Boyer, C. . Copolymers with controlled molecular weight distributions and compositional gradients through flow polymerization . Macromolecules , 2018 . 51 4553 - 4563 . DOI: 10.1021/acs.macromol.8b00673 http://doi.org/10.1021/acs.macromol.8b00673 .

Corrigan, N.; Zhernakov, L.; Hashim, M. H.; Xu, J.; Boyer, C. . Flow mediated metal-free PET-RAFT polymerisation for upscaled and consistent polymer production . React. Chem. Eng. , 2019 . 4 1216 - 1228 . DOI: 10.1039/C9RE00014C http://doi.org/10.1039/C9RE00014C .

Zhou, Y.; Gu, Y.; Jiang, K. M.; Chen, M. . Droplet-flow photopolymerization aided by computer: overcoming the challenges of viscosity and facilitating the generation of copolymer libraries . Macromolecules , 2019 . 52 5611 - 5617 . DOI: 10.1021/acs.macromol.9b00846 http://doi.org/10.1021/acs.macromol.9b00846 .

Kohler, J. M.; Li, S. N.; Knauer, A. . Why is micro segmented flow particularly promising for the synthesis of nanomaterials? . Chem. Eng. Technol. , 2013 . 36 887 - 899 . DOI: 10.1002/ceat.201200695 http://doi.org/10.1002/ceat.201200695 .

Noel, T.; Buchwald, S. L. . Cross-coupling in flow . Chem. Soc. Rev. , 2011 . 40 5010 - 5029 . DOI: 10.1039/c1cs15075h http://doi.org/10.1039/c1cs15075h .

Horie, T.; Sumino, M.; Tanaka, T.; Matsushita, Y.; Ichimura, T.; Yoshida, J. . Photodimerization of maleic anhydride in a microreactor without clogging . Org. Process Res. Dev. , 2010 . 14 405 - 410 . DOI: 10.1021/op900306z http://doi.org/10.1021/op900306z .

DesLauriers, P. J.; McDaniel, M. P.; Rohlfing, D. C.; Krishnaswamy, R. K.; Secora, S. J.; Benham, E. A.; Maeger, P. L.; Wolfe, A. R.; Sukhadia, A. M.; Beaulieu, B. B. . A comparative study of multimodal vs. bimodal polyethylene pipe resins for PE-100 applications . Polym. Eng. Sci. , 2005 . 45 1203 - 1213 . .

Kukalyekar, N.; Balzano, L.; Peters, G. W. M.; Rastogi, S.; Chadwick, J. C. . Characteristics of bimodal polyethylene prepared via co-immobilization of chromium and iron catalysts on an MgCl 2 -based support . Macromol. React. Eng. , 2009 . 3 448 - 454 . DOI: 10.1002/mren.200900021 http://doi.org/10.1002/mren.200900021 .

Ramsey, B. L.; Pearson, R. M.; Beck, L. R.; Miyake, G. M. . Photoinduced organocatalyzed atom transfer radical polymerization using continuous flow . Macromolecules , 2017 . 50 2668 - 2674 . DOI: 10.1021/acs.macromol.6b02791 http://doi.org/10.1021/acs.macromol.6b02791 .

Kuroki, A.; Martinez-Botella, I.; Hornung, C. H.; Martin, L.; Williams, E. G. L.; Locock, K. E. S.; Hartlieb, M.; Perrier, S. . Looped flow RAFT polymerization for multiblock copolymer synthesis . Polym. Chem. , 2017 . 8 3249 - 3254 . DOI: 10.1039/C7PY00630F http://doi.org/10.1039/C7PY00630F .

Gong, H.; Zhao, Y.; Shen, X.; Lin, J.; Chen, M. . Organocatalyzed photocontrolled radical polymerization of semifluorinated (meth)acrylates driven by visible light . Angew. Chem. Int. Ed. , 2018 . 57 333 - 337 . DOI: 10.1002/anie.201711053 http://doi.org/10.1002/anie.201711053 .

Morsbach, J.; Müller, A. H. E.; Berger-Nicoletti, E.; Frey, H. . Living polymer chains with predictable molecular weight and dispersity via carbanionic polymerization in continuous flow: mixing rate as a key parameter . Macromolecules , 2016 . 49 5043 - 5050 . DOI: 10.1021/acs.macromol.6b00975 http://doi.org/10.1021/acs.macromol.6b00975 .

Endo, Y.; Furusawa, M.; Shimazaki, T.; Takahashi, Y.; Nakahara, Y.; Nagaki, A. . Molecular weight distribution of polymers produced by anionic polymerization enables mixability evaluation . Org. Process Res. Dev. , 2019 . 23 635 - 640 . DOI: 10.1021/acs.oprd.8b00403 http://doi.org/10.1021/acs.oprd.8b00403 .

Nagaki, A.; Miyazaki, A.; Yoshida, J. I. . Synthesis of polystyrenes-poly(alkyl methacrylates) block copolymers via anionic polymerization using an integrated flow microreactor system . Macromolecules , 2010 . 43 8424 - 8429 . DOI: 10.1021/ma101663x http://doi.org/10.1021/ma101663x .

Nagaki, A.; Kawamura, K.; Suga, S.; Ando, T.; Sawamoto, M.; Yoshida, J. . Cation pool-initiated controlled/living polymerization using microsystems . J. Am. Chem. Soc. , 2004 . 126 14702 - 14703 . DOI: 10.1021/ja044879k http://doi.org/10.1021/ja044879k .

Wang, E.; Chen, M. . Catalyst shuttling enabled by a thermoresponsive polymeric ligand: facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium . Chem. Sci. , 2019 . 10 8331 - 8337 . DOI: 10.1039/C9SC02171J http://doi.org/10.1039/C9SC02171J .

Zhong, F.; Zhou, Y.; Chen, M. . The influence of mixing on chain extension by photo-controlled/living radical polymerization under continuous-flow conditions . Polym. Chem. , 2019 . 10 4879 - 4886 . DOI: 10.1039/C9PY01063G http://doi.org/10.1039/C9PY01063G .

Yeow, J.; Boyer, C. . Photoinitiated polymerization-induced self-assembly (photo-PISA): new insights and opportunities . Adv. Sci. , 2017 . 4 1700137 DOI: 10.1002/advs.201700137 http://doi.org/10.1002/advs.201700137 .

Warren, N. J.; Armes, S. P. . Polymerization-induced self-assembly of block copolymer nano-objects via RAFT aqueous dispersion polymerization . J. Am. Chem. Soc. , 2014 . 136 10174 - 10185 . DOI: 10.1021/ja502843f http://doi.org/10.1021/ja502843f .

Zeng, R. M.; Chen, Y.; Zhang, L.; Tan, J. B. . R-RAFT or Z-RAFT? Well-defined star block copolymer nano-objects prepared by RAFT-mediated polymerization-induced self-assembly . Macromolecules , 2020 . 53 1557 - 1566 . DOI: 10.1021/acs.macromol.0c00123 http://doi.org/10.1021/acs.macromol.0c00123 .

Li, H. H.; Xu, Q. H.; Xu, X.; Zhang, L. F.; Cheng, Z. P.; Zhu, X. L. . One-step photocontrolled polymerization-induced self-assembly (photo-PISA) by using in situ bromine-iodine transformation reversible-deactivation radical polymerization . Polymers , 2020 . 12 150 DOI: 10.3390/polym12010150 http://doi.org/10.3390/polym12010150 .

Zaquen, N.; Yeow, J.; Junkers, T.; Boyer, C.; Zetterlund, P. B. . Visible light-mediated polymerization-induced self-assembly using continuous flow reactors . Macromolecules , 2018 . 51 5165 - 5172 . DOI: 10.1021/acs.macromol.8b00887 http://doi.org/10.1021/acs.macromol.8b00887 .

Zaquen, N.; Azizi, W. A. A. W.; Yeow, J.; Kuchel, R. P.; Junkers, T.; Zetterlund, P. B.; Boyer, C. . Alcohol-based PISA in batch and flow: exploring the role of photoinitiators . Polym. Chem. , 2019 . 10 2406 - 2414 . DOI: 10.1039/C9PY00166B http://doi.org/10.1039/C9PY00166B .

Quan, Q.; Gong, H.; Chen, M. . Preparation of semifluorinated poly(meth)acrylates by improved photo-controlled radical polymerization without the use of a fluorinated RAFT agent: facilitating surface fabrication with fluorinated materials . Polym. Chem. , 2018 . 9 4161 - 4171 . DOI: 10.1039/C8PY00990B http://doi.org/10.1039/C8PY00990B .

Zaquen, N.; Zu, H.; Kadir, A. M. N. B. P. H. A.; Junkers, T.; Zetterlund, P. B.; Boyer, C. . Scalable aqueous reversible addition-fragmentation chain transfer photopolymerization-induced self-assembly of acrylamides for direct synthesis of polymer nanoparticles for potential drug delivery applications . ACS Appl. Polym. Mater. , 2019 . 1 1251 - 1256 . .

Liu, D.; Cai, W.; Zhang, L.; Boyer, C.; Tan, J. . Efficient photoinitiated polymerization-induced self-assembly with oxygen tolerance through fual-wavelength type I photoinitiation and photoinduced deoxygenation . Macromolecules , 2020 . 53 1212 - 1223 . DOI: 10.1021/acs.macromol.9b02710 http://doi.org/10.1021/acs.macromol.9b02710 .

Lin, B.; Hedrick, J. L.; Park, N. H.; Waymouth, R. M. . Programmable high-throughput platform for the rapid and scalable synthesis of polyester and polycarbonate libraries . J. Am. Chem. Soc. , 2019 . 141 8921 - 8927 . DOI: 10.1021/jacs.9b02450 http://doi.org/10.1021/jacs.9b02450 .

van de Walle, M.; De Bruycker, K.; Junkers, T.; Blinco, J. P.; Barner-Kowollik, C. . Scalable synthesis of sequence-defined oligomers via photoflow chemistry . ChemPhotoChem , 2019 . 3 225 - 228 . DOI: 10.1002/cptc.201900031 http://doi.org/10.1002/cptc.201900031 .

Walsh, D. J.; Schinski, D. A.; Schneider, R. A.; Guironnet, D. . General route to design polymer molecular weight distributions through flow chemistry . Nat. Commun. , 2020 . 11 3094 DOI: 10.1038/s41467-020-16874-6 http://doi.org/10.1038/s41467-020-16874-6 .

Harper, K. C.; Moschetta, E. G.; Bordawekar, S. V.; Wittenberger, S. J. . A laser driven flow chemistry platform for scaling photochemical reactions with visible light . ACS Cent. Sci. , 2019 . 5 109 - 115 . DOI: 10.1021/acscentsci.8b00728 http://doi.org/10.1021/acscentsci.8b00728 .

Laudadio, G.; Deng, Y.; van der Wal, K.; Ravelli, D.; Nuño, M.; Fagnoni, M.; Guthrie, D.; Sun, Y.; Noël, T. . C(sp 3 )-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow . Science , 2020 . 369 92 - 96 . DOI: 10.1126/science.abb4688 http://doi.org/10.1126/science.abb4688 .

Ge, L.; Yan, J.; Song, X.; Yan, M.; Ge, S.; Yu, J. . Three-dimensional paper-based electrochemiluminescence immunodevice for multiplexed measurement of biomarkers and point-of-care testing . Biomaterials , 2012 . 33 1024 - 1031 . DOI: 10.1016/j.biomaterials.2011.10.065 http://doi.org/10.1016/j.biomaterials.2011.10.065 .

Yeo, L. Y.; Chang, H. C.; Chan, P. P.; Friend, J. R. . Microfluidic devices for bioapplications . Small , 2011 . 7 12 - 48 . DOI: 10.1002/smll.201000946 http://doi.org/10.1002/smll.201000946 .

Rubens, M.; Vrijsen, J. H.; Laun, J.; Junkers, T. . Precise polymer synthesis by autonomous self-optimizing flow reactors . Angew. Chem. Int. Ed. , 2019 . 58 3183 - 3187 . DOI: 10.1002/anie.201810384 http://doi.org/10.1002/anie.201810384 .

Gentekos, D. T.; Sifri, R. J.; Fors, B. P. . Controlling polymer properties through the shape of the molecular-weight distribution . Nat. Rev. Mater. , 2019 . 4 761 - 774 . DOI: 10.1038/s41578-019-0138-8 http://doi.org/10.1038/s41578-019-0138-8 .

Whitfield, R.; Truong, N. P.; Messmer, D.; Parkatzidis, K.; Rolland, M.; Anastasaki, A. . Tailoring polymer dispersity and shape of molecular weight distributions: methods and applications . Chem. Sci. , 2019 . 10 8724 - 8734 . DOI: 10.1039/C9SC03546J http://doi.org/10.1039/C9SC03546J .

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