

FOLLOWUS
a.Istanbul Technical University, Department of Chemistry, Maslak, 34469 Istanbul, Turkey
b.Center of Excellence for Advanced Materials Research (CEAMR) and Department of Chemistry, Faculty of Science, King Abdulaziz University, 21589 Jeddah, Saudi Arabia
yusuf@itu.edu.tr
Received:01 October 2019,
Revised:2019-10-28,
Accepted:29 October 2019,
Online First:27 November 2019,
Published:2020-03
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Yilmaz, G.; Yagci, Y. Mechanistic transformations involving radical and cationic polymerizations. Chinese J. Polym. Sci. 2020, 38, 205–212.
Gorkem Yilmaz, Yusuf Yagci. Mechanistic Transformations Involving Radical and Cationic Polymerizations[J]. Chinese Journal of Polymer Science, 2020, 38(3): 205-212.
Yilmaz, G.; Yagci, Y. Mechanistic transformations involving radical and cationic polymerizations. Chinese J. Polym. Sci. 2020, 38, 205–212. DOI: 10.1007/s10118-020-2367-0.
Gorkem Yilmaz, Yusuf Yagci. Mechanistic Transformations Involving Radical and Cationic Polymerizations[J]. Chinese Journal of Polymer Science, 2020, 38(3): 205-212. DOI: 10.1007/s10118-020-2367-0.
Mechanistic transformation approach has been widely applied in polymer synthesis due to its unique feature combining structurally different polymers prepared by different polymerization mechanisms. Reported methods for the formation of block and graft copolymers through mechanistic transformation involve almost all polymerizations modes. However
certain polymerization processes require extensive purification processes
which can be time-consuming and problematic. Recent developments on controlled/living polymerizations involving radical and cationic mechanisms with the ability to control molecular weight and functionality led to new pathways for mechanistic transformations. In this mini-review
we systematically discussed relevant advances in the field through three main titles namely (i) from radical to cationic mechanism
(ii) from cationic to radical mechanism
and (iii) application of specific catalyst systems for both radical and cationic polymerizations.
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 .
Wang, J. S.; Matyjaszewski, K. . Controlled/"living" radical polymerization. Halogen atom-transfer radical polymerization promoted by a Cu(I)Cu(II) redox process . Macromolecules , 1995 . 28 7901 - 7910 . DOI: 10.1021/ma00127a042 http://doi.org/10.1021/ma00127a042 .
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 .
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 .
Sawamoto, M. . Modern cationic vinyl polymerization . Prog. Polym. Sci. , 1991 . 16 111 - 172 . DOI: 10.1016/0079-6700(91)90008-9 http://doi.org/10.1016/0079-6700(91)90008-9 .
Kamigaito, M.; Ando, T.; Sawamoto, M. . Metal-catalyzed living radical polymerization . Chem. Rev. , 2001 . 101 3689 - 3745 . DOI: 10.1021/cr9901182 http://doi.org/10.1021/cr9901182 .
Guo, X.; Choi, B.; Feng, A.; Thang, S. H. . Polymer synthesis with more than one form of living polymerization method . Macromol. Rapid Commun. , 2018 . 39 1800479 DOI: 10.1002/marc.201800479 http://doi.org/10.1002/marc.201800479 .
Higashimura, T.; Aoshima, S.; Sawamoto, M. . New initiators for living cationic polymerization of vinyl compounds . Makromol. Chem. Makromol. Symp. , 1988 . 13-4 457 - 471 . .
Sawamoto, M.; Okamoto, C.; Higashimura, T. . Hydrogen iodide zinc iodide—a new initiating system for living cationic polymerization of vinyl ethers at room-temperature . Macromolecules , 1987 . 20 2693 - 2697 . DOI: 10.1021/ma00177a010 http://doi.org/10.1021/ma00177a010 .
Yagci, Y.; Schnabel, W. . Light-induced cationic polymerization . Makromol. Chem. Macromol. Symp. , 1988 . 13-14 161 - 174 . DOI: 10.1002/masy.19880130113 http://doi.org/10.1002/masy.19880130113 .
Kolb, H. C.; Finn, M. G.; Sharpless, K. B. . Click chemistry: diverse chemical function from a few good reactions . Angew. Chem. Int. Ed. , 2001 . 40 2004 - 2021 . DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 http://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 .
Barner-Kowollik, C.; Du Prez, F. E.; Espeel, P.; Hawker, C. J.; Junkers, T.; Schlaad, H.; van Camp, W. . "Clicking" polymers or just efficient linking: what is the difference? . Angew. Chem. Int. Ed. , 2011 . 50 60 - 62 . DOI: 10.1002/anie.201003707 http://doi.org/10.1002/anie.201003707 .
Yagci, Y.; Tasdelen, M. A. . Mechanistic transformations involving living and controlled/living polymerization methods . Prog. Polym. Sci. , 2006 . 31 1133 - 1170 . DOI: 10.1016/j.progpolymsci.2006.07.003 http://doi.org/10.1016/j.progpolymsci.2006.07.003 .
Burgess, F. J.; Cunliffe, A. V.; MacCallum, J. R.; Richards, D. H. . Reactions to effect the transformation of anionic polymerization into cationic polymerization: 2. Synthesis and reactivities of anionically generated xylelene bromide-terminated polymers . Polymer , 1977 . 18 726 - 732 . .
Burgess, F. J.; Cunliffe, A. V.; MacCallum, J. R.; Richards, D. H. . Reaction to effect the transformation of anionic polymerization into cationic polymerization: 1. Synthesis and reactivities of anionically generated bromine terminated polymers . Polymer , 1977 . 18 719 - 725 . .
Schäfer, M.; C., Wieland P.; Nuyken, O. . Synthesis of new graft copolymers containing polyisobutylene by a combination of the 1,1-diphenylethylene technique and cationic polymerization . J. Polym. Sci., Part A: Polym. Chem. , 2002 . 40 3725 - 3733 . DOI: 10.1002/pola.10472 http://doi.org/10.1002/pola.10472 .
Düz, A. B.; Hizal, G.; Yagci, Y. . Block copolymers by transformation of living ring opening polymerization into an initer process . Eur. Polym. J. , 2000 . 36 1373 - 1378 . DOI: 10.1016/S0014-3057(99)00189-5 http://doi.org/10.1016/S0014-3057(99)00189-5 .
Kumagai, S.; Nagai, K.; Satoh, K.; Kamigaito, M. . In-situ direct mechanistic transformation from raft to living cationic polymerization for (meth)acrylate-vinyl ether block copolymers . Macromolecules , 2010 . 43 7523 - 7531 . DOI: 10.1021/ma101420u http://doi.org/10.1021/ma101420u .
Kahveci, M. U.; Acik, G.; Yagci, Y. . Synthesis of block copolymers by combination of atom transfer radical polymerization and visible light-induced free radical promoted cationic polymerization . Macromol. Rapid Commun. , 2012 . 33 309 - 313 . DOI: 10.1002/marc.201100641 http://doi.org/10.1002/marc.201100641 .
Yagci, Y. . Block copolymers by combinations of cationic and radical routes 1. A new difunctional azo-oxocarbenium initiator for cationic polymerization . Polym. Commun. , 1985 . 26 7 - 8 . .
Galli, G.; Chiellini, E.; Yagci, Y.; Serhatli, E. I.; Laus, M.; Bignozzi, M. C.; Angeloni, A. S. . Block copolymers with crystalline and side-chain liquid crystalline blocks . Makromol. Chem. Rapid Commun. , 1993 . 14 185 - 193 . DOI: 10.1002/marc.1993.030140307 http://doi.org/10.1002/marc.1993.030140307 .
Hizal, G.; Tasdemir, H.; Yagci, Y. . Block copolymers by combination of cationic and radical routes: 5. Polymerization of styrene initiated by 4,4′-azobis(4-cyanopentanoyl chloride) . Polymer , 1990 . 31 1803 - 1806 . .
Yagci, Y.; Onen, A.; Schnabel, W. . Block copolymers by combination radical and promoted cationic polymerization routes . Macromolecules , 1991 . 24 4620 - 4623 . DOI: 10.1021/ma00016a023 http://doi.org/10.1021/ma00016a023 .
Hepuzer, Y.; Yagci, Y.; Biedron, T.; Kubisa, P. . Photoactive epichlorohydrin 2. Photoinitiated free-radical and promoted cationic polymerization by using polyepichlorohydrin with benzoin terminal groups . Angew. Makromol. Chem. , 1996 . 237 163 - 171 . .
Onen, A.; Yagci, Y.; Schnabel, W. . Synthesis of benzoin terminated poly(tetrahydrofuran)s . Angew. Makromol. Chem. , 1996 . 243 143 - 149 . DOI: 10.1002/apmc.1996.052430112 http://doi.org/10.1002/apmc.1996.052430112 .
Hizal, G.; Yagci, Y.; Schnabel, W. . N-alkoxy pyridinium ion terminated polytetrahydrofurans—synthesis and their use in photoinitiated block copolymerization . Polymer , 1994 . 35 4443 - 4448 . DOI: 10.1016/0032-3861(94)90105-8 http://doi.org/10.1016/0032-3861(94)90105-8 .
Le, D.; Phan, T. N. T.; Autissier, L.; Charles, L.; Gigmes, D. . A well-defined block copolymer synthesis via living cationic polymerization and nitroxide-mediated polymerization using carboxylic acid-based alkoxyamines as a dual initiator . Polym. Chem. , 2016 . 7 1659 - 1667 . DOI: 10.1039/C5PY01934F http://doi.org/10.1039/C5PY01934F .
Yamada, K.; Miyazaki, M.; Ohno, K.; Fukuda, T.; Minoda, M. . Atom transfer radical polymerization of poly(vinyl ether) macromonomers . Macromolecules , 1999 . 32 290 - 293 . DOI: 10.1021/ma981415w http://doi.org/10.1021/ma981415w .
Li, M.; Zhang, L.; Tao, M.; Cheng, Z.; Zhu, X. . Living cationic polymerization of bisazobenzene-containing vinyl ether and synthesis of a graft copolymer by combination with ATRP . Polym. Chem. , 2014 . 5 4076 - 4082 . DOI: 10.1039/C4PY00162A http://doi.org/10.1039/C4PY00162A .
Zhu, Y.; Storey, R. F. . Synthesis of polyisobutylene-based miktoarm star polymers from a dicationic monoradical dual initiator . Macromolecules , 2012 . 45 5347 - 5357 . DOI: 10.1021/ma3007762 http://doi.org/10.1021/ma3007762 .
Sugihara, S.; Konegawa, N.; Maeda, Y. . HCl·Et 2 O-catalyzed metal-free RAFT cationic polymerization: one-pot transformation from metal-free living cationic polymerization to RAFT radical polymerization 1 . Macromolecules , 2015 . 48 5120 - 5131 . DOI: 10.1021/acs.macromol.5b01071 http://doi.org/10.1021/acs.macromol.5b01071 .
Sugihara, S.; Yamashita, K.; Matsuzuka, K.; Ikeda, I.; Maeda, Y. . Transformation of living cationic polymerization of vinyl ethers to RAFT polymerization mediated by a carboxylic RAFT agent . Macromolecules , 2012 . 45 794 - 804 . DOI: 10.1021/ma201988n http://doi.org/10.1021/ma201988n .
Yoshida, E.; Sugita, A. . Synthesis of poly(tetrahydrofuran) with a nitroxyl radical at the chain end and its application to living radical polymerization . Macromolecules , 1996 . 29 6422 - 6426 . DOI: 10.1021/ma9605210 http://doi.org/10.1021/ma9605210 .
Yildirim, T. G.; Hepuzer, Y.; Hizal, G.; Yagci, Y. . Synthesis of block copolymers by transformation of photosensitized cationic polymerization to stable free radical polymerization . Polymer , 1999 . 40 3885 - 3890 . DOI: 10.1016/S0032-3861(98)00633-8 http://doi.org/10.1016/S0032-3861(98)00633-8 .
Kajiwara, A.; Matyjaszewski, K. . Formation of block copolymers by transformation of cationic ring-opening polymerization to atom transfer radical polymerization (ATRP) . Macromolecules , 1998 . 31 3489 - 3493 . DOI: 10.1021/ma971445j http://doi.org/10.1021/ma971445j .
Puglisi, A.; Murtezi, E.; Yilmaz, G.; Yagci, Y. . Synthesis of block copolymers by mechanistic transformation from photoinitiated cationic polymerization to a RAFT process . Polym. Chem. , 2017 . 8 7307 - 7310 . DOI: 10.1039/C7PY01707C http://doi.org/10.1039/C7PY01707C .
Uchiyama, M.; Satoh, K.; Kamigaito, M. . Cationic RAFT polymerization using ppm concentrations of organic acid . Angew. Chem. Int. Ed. , 2015 . 54 1924 - 1928 . DOI: 10.1002/anie.201410858 http://doi.org/10.1002/anie.201410858 .
Ciftci, M.; Yoshikawa, Y.; Yagci, Y. . Living cationic polymerization of vinyl ethers through a photoinduced radical oxidation/addition/deactivation sequence . Angew. Chem. Int. Ed. , 2017 . 56 519 - 523 . DOI: 10.1002/anie.201609357 http://doi.org/10.1002/anie.201609357 .
Ciftci, M.; Yagci, Y. . Block copolymers by mechanistic transformation from proad to iniferter process . Macromol. Rapid Commun. , 2018 . 39 .
Li, J.; Zhang, M.; Pan, X.; Zhang, Z.; Perrier, S.; Zhu, J.; Zhu, X. . Visible light induced controlled cationic polymerization by in situ generated catalyst from manganese carbonyl . Chem. Commun. , 2019 . 55 7045 - 7048 . DOI: 10.1039/C9CC03317C http://doi.org/10.1039/C9CC03317C .
Aoshima, H.; Satoh, K.; Kamigaito, M. . In situ direct mechanistic transformation from FeCl 3 -catalyzed living cationic to radical polymerizations . Macromol. Symp. , 2013 . 323 64 - 74 . DOI: 10.1002/masy.201100115 http://doi.org/10.1002/masy.201100115 .
Satoh, K.; Hashimoto, H.; Kumagai, S.; Aoshima, H.; Uchiyama, M.; Ishibashi, R.; Fujiki, Y.; Kamigaito, M. . One-shot controlled/living copolymerization for various comonomer sequence distributions via dual radical and cationic active species from RAFT terminals . Polym. Chem. , 2017 . 8 5002 - 5011 . DOI: 10.1039/C7PY00324B http://doi.org/10.1039/C7PY00324B .
Peterson, B. M.; Kottisch, V.; Supej, M. J.; Fors, B. P. . On demand switching of polymerization mechanism and monomer selectivity with orthogonal stimuli . ACS Cent. Sci. , 2018 . 4 1228 - 1234 . DOI: 10.1021/acscentsci.8b00401 http://doi.org/10.1021/acscentsci.8b00401 .
Uchiyama, M.; Satoh, K.; McKenzie, T. G.; Fu, Q.; Qiao, G. G.; Kamigaito, M. . Diverse approaches to star polymers via cationic and radical RAFT cross-linking reactions using mechanistic transformation . Polym. Chem. , 2017 . 8 5972 - 5981 . DOI: 10.1039/C7PY01401E http://doi.org/10.1039/C7PY01401E .
Guerre, M.; Uchiyama, M.; Folgado, E.; Semsarilar, M.; Ameduri, B.; Satoh, K.; Kamigaito, M.; Ladmiral, V. . Combination of cationic and radical RAFT polymerizations: a versatile route to well-defined poly(ethyl vinyl ether)-block-poly(vinylidene fluoride) block copolymers . ACS Macro Lett. , 2017 . 6 393 - 398 . DOI: 10.1021/acsmacrolett.7b00150 http://doi.org/10.1021/acsmacrolett.7b00150 .
Guerre, M.; Uchiyama, M.; Lopez, G.; Ameduri, B.; Satoh, K.; Kamigaito, M.; Ladmiral, V. . Synthesis of PEVE- b -P(CTFE- alt -EVE) block copolymers by sequential cationic and radical RAFT polymerization . Polym. Chem. , 2018 . 9 352 - 361 . DOI: 10.1039/C7PY01924F http://doi.org/10.1039/C7PY01924F .
Aoshima, H.; Uchiyama, M.; Satoh, K.; Kamigaito, M. . Interconvertible living radical and cationic polymerization through reversible activation of dormant species with dual activity . Angew. Chem. Int. Ed. , 2014 . 53 10932 - 10936 . DOI: 10.1002/anie.201406590 http://doi.org/10.1002/anie.201406590 .
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