Research progress of photoinduced reversible deactivation radical polymerization in the presence of alkyliodidie

doi:10.16085/j.issn.1000-6613.2019-2031

Abstract

Abstract:

Photoinduced reversible deactivation radical polymerization in the presence of alkyl iodidie has many attractive features such as simple system composition, wide range wavelengths of light source. This paper summarized the photoinduced RDRP with iodocompounds and cross applications of this polymerization method in recent years, including photoinduced iodine transfer polymerization, photoinduced reversible complexation mediated polymerization. This paper gave a review of the basic mechanism of polymerization, applicability to different-wavelength light sources. Moreover, the preparation of polymer “brush” and polymerization induced self-assembly by photoinduced reversible complexation mediated polymerization were also discussd.

Key words: reversible deactivation radical polymerization (RDRP), photoinduced iodine transfer polymerization, photoinduced reversible complexation mediated polymerization

摘要：

碘代化合物存在下光引发的可逆-休眠自由基聚合（reversible deactivation radical polymerization, RDRP）具有体系组成简单、适用光源波长范围宽等优点，近年来受到广泛关注。本文主要介绍了最近几年碘代化合物存在下光引发的可逆-休眠自由基聚合的研究进展，以及该聚合方法与其他研究方向的交叉应用。具体包括：光引发的碘转移聚合、光引发的可逆络合聚合以及这些聚合方法在其它研究方向的应用。概述了聚合机理、聚合适用的光源，以及上述聚合方法作为工具实现聚合物“刷”的制备和诱导自组装（polymerization-induced self-Assembly，PISA），实现了不同聚合物形貌的设计。

关键词: 可逆-休眠自由基聚合, 光引发的碘转移聚合, 光引发的可逆络合聚合

CLC Number:

Xu ZHANG, Kelong CHEN. Research progress of photoinduced reversible deactivation radical polymerization in the presence of alkyliodidie[J]. Chemical Industry and Engineering Progress, 2020, 39(S1): 1-11.

张旭, 陈珂龙. 碘代化合物存在下光引发的可逆-休眠自由基聚合研究进展[J]. 化工进展, 2020, 39(S1): 1-11.

Figures/Tables 17

References 69

1	OTSU T, YOSHIDA M. Role of initiator-transfer agent-terminator (Iniferter) in radical polymerizations-polymer design by organic disulfides as iniferters[J]. Macromolecular Rapid Communications, 1982, 3( 2): 127- 132.
2	HAWKER C J, BOSMAN A W, HARTH E. New polymer synthesis by nitroxide mediated living radical polymerization[J]. Chemical Reviews, 2001, 101: 3661- 3688.
3	NICOLAS J, GUILLANEUF Y, BERTIN D, et al. Nitroxide-mediated polymerization[J]. Polymer Science, 2013, 38: 63- 235.
4	MATYJASZEWSKI K, PATTEN T E, XIA J. Controlled/"living" radical polymerization. kinetics of the homogeneous atom transfer radical polymerization of styrene[J]. Journal of the American Chemistry Society, 1997, 119: 674- 680.
5	MATYJASZEWSKI K, XIA J. Atom transfer radical polymerization[J]. Chemical Reviews, 2001, 101: 2921- 2990.
6	FAVIER A, M-T CHARREYRE. Experimental requirements for an efficient control of free-radical polymerizations via the reversible addition-fragmentation chain transfer (PAFT) process[J]. Macromolecular Rapid Communications, 2006, 27( 9): 653- 692.
7	CHIEFARI J, CHONG Y K B, ERCOLE F, et al. Living free-radical polymerization by reversible addition-fragmentation chain transfer: the RAFT process[J]. Macromolecules, 1998, 31: 5559- 5562.
8	JENKINS A D, JONES R G, MOAD G. Terminology for reversible-deactivation radical polymerization previously called "controlled" radical or "living" radical polymerization (IUPAC recommendations 2010)[J]. Pure and Applied Chemistry, 2009, 82( 2): 483- 491.
9	MATYJASZEWSKI K. Controlled radical polymerization: state-of-the-art in 2011[J]. ACS Symposium Series, 2015, 1100: 1- 17.
10	CHEN M, MACLEOD M J, JOHNSON J A. Visible-light-controlled living radical polymerization from a trithiocarbonate iniferter mediated by an organic photoredox catalyst[J]. ACS Macro. Letters, 2015, 4( 5): 566- 569.
11	PERKOWSKI A J, YOU W, NICEWICZ D A. Visible light photoinitiated metal-free living cationic polymerization of 4-methoxystyrene[J]. Journal of the American Chemister Society, 2015, 137( 24): 7580- 7583.
12	WOLPERS A, VANA P. UV light as external switch and boost of molar-mass control in iodine-mediated polymerization[J]. Macromolecules, 2014, 47( 3): 954- 963.
13	YOSHIDA E. Effects of initiators and photo-acid generators on nitroxide-mediated photo-living radical polymerization of methyl methacrylate[J]. Colloid and Polymer Science, 2010, 288( 8): 901- 905.
14	YOSHIDA E. Nitroxide-mediated photo-living radical polymerization of methyl methacrylate in solution[J]. Colloid and Polymer Science, 2010, 288( 16/17): 1639- 1643.
15	DEBUIGNE A, SCHOUMACHER M, WILLET N, et al. New functional poly(N-vinylpyrrolidone) based ( co)polymers via photoinitiated cobalt-mediated radical polymerization[J]. Chem. Commun. (Camb), 2011, 47( 47): 12703- 12705.
16	DETREMBLEUR C, D-L VERSACE, PIETTE Y, et al. Synthetic and mechanistic inputs of photochemistry into the bis-acetylacetonatocobalt- mediated radical polymerization of n-butyl acrylate and vinyl acetate[J]. Polymer Chemistry, 2012, 3( 7): 1856- 1866.
17	NAKAMURA Y, ARIMA T, TOMITA S, et al. Photoinduced switching from living radical polymerization to a radical coupling reaction mediated by organotellurium compounds[J]. Journal of the American Chemistry Society, 2012, 134( 12): 5536- 5539.
18	PAN X, MALHOTRA N, SIMAKOVA A, et al. Photoinduced atom transfer radical polymerization with ppm-level Cu catalyst by visible light in aqueous media[J]. Journal of the American Chemistry Society, 2015, 137( 49): 15430- 15433.
19	FU L, WANG Z, LATHWAL S, et al. Synthesis of polymer bioconjugates via photoinduced atom transfer radical polymerization under blue light irradiation[J]. ACS Macro. Letters, 2018, 7( 10): 1248- 1253.
20	LEI L, LI F, ZHAO H, et al. One-pot synthesis of block copolymers by ring-opening polymerization and ultraviolet light-induced ATRP at ambient temperature[J]. Journal of Polymer Science Part A: Polymer Chemistry, 2018, 56( 7): 699- 704.
21	WANG L, LI R, ZHANG K. Atom transfer radical polymerization (ATRP) catalyzed by visible light-absorbed small molecule organic semiconductors[J]. Macromol. Rapid Commun., 2018, 39( 18): e1800466.
22	NI B, WANG D, ZHANG H, et al. Visible light controlled polymerization of azide‐derived monomers: a facile, metal‐free pet‐ATRP route to construct azide polymers[J]. Macromolecular Chemistry and Physics, 2019, 220( 7): 1800529.
23	ROLLAND M, WHITFIELD R, MESSMER D, et al. Effect of polymerization components on oxygen-tolerant photo-ATRP[J]. ACS Macro. Letters, 2019, 1546- 1551.
24	XU J, JUNG K, ATME A, et al. A robust and versatile photoinduced living polymerization of conjugated and unconjugated monomers and its oxygen tolerance[J]. Journal of the American Chemistry Society, 2014, 136( 14): 5508- 5519.
25	XU J, JUNG K, BOYER C. Oxygen tolerance study of photoinduced electron transfer-reversible addition-fragmentation chain transfer (PET-RAFT) polymerization mediated by Ru(bpy) ₃Cl ₂[J]. Macromolecules, 2014, 47( 13): 4217- 4229.
26	BOYER C, VALADE D, SAUGUET L, et al. Iodine transfer polymerization (ITP) of vinylidene fluoride (VDF). influence of the defect of VDF chaining on the control of ITP[J]. Macromolecules, 2005, 38( 25): 10353- 10362.
27	BOUTEVIN B, FURET Y, HERVAUD Y, et al. Etude de la télomérisation et de la cotélomérisation du fluorure de vinylidéne (VF2). Part I. Cotélomérisation du VF2 avec l′acétate de vinyleetle 2-hydroxyéthylmercaptan[J]. Journal of Fluorine Chemistry, 1994, 69( 1): 11- 18.
28	WANG Y A, SHI Y, FU Z F, et al. Hexamethylphosphoramide as a highly reactive catalyst for reversible-deactivation radical polymerization of MMA with in-situ formed alkyl iodide initiator[J]. Polymer Chemistry, 2017, 8: 6073- 6085.
29	ASANDEI A D, ADEBOLU O I, SIMPSON C P, et al. Visible-light hypervalent iodide carboxylate photo(trifluoro)methylations and controlled radical polymerization of fluorinated alkenes[J]. Angew. Chem. Int. Ed. Engl., 2013, 52( 38): 10027- 10030.
30	GOTO A, SUZUKI T, OHFUJI H, et al. Reversible complexation mediated living radical polymerization (RCMP) using organic catalysts[J]. Macromolecules, 2011, 44( 22): 8709- 8715.
31	GOTO A, OHTSUKI A, OHFUJI H, et al. Reversible generation of a carbon-centered radical from alkyl iodide using organic salts and their application as organic catalysts in living radical polymerization[J]. Journal of the American Chemistry Society, 2013, 135( 30): 11131- 11139.
32	GOTO A, TANISHIMA M, NAKAJIMA Y, et al. Living radical polymerizations using sodium iodide and potassium iodide as catalysts[J]. Macromolecules, 2015, 1187: 171- 182.
33	LEI L, TANISHIMA M, GOTO A, et al. Living radical polymerization via organic superbase catalysis[J]. Polymers, 2014, 6( 3): 860- 872.
34	WANG W, BAI L, CHEN H, et al. PMDETA as an efficient catalyst for bulk reversible complexation mediated polymerization (RCMP) in the absence of additional metal salts and deoxygenation[J]. RSC Advances, 2016, 6( 99): 97455- 97462.
35	WANG C G, HANINDITA F, GOTO A. Biocompatible choline iodide catalysts for green living radical polymerization of functional polymers[J]. ACS Macro. Letters, 2018, 7( 2): 263- 268.
36	OHTSUKI A, GOTO A, KAJI H. Visible-light-induced reversible complexation mediated living radical polymerization of methacrylates with organic catalysts[J]. Macromolecules, 2012, 46( 1): 96- 102.
37	TONNAR J, LACROIX-DESMAZES P, BOUTEVIN B. Living radical ab initio emulsion polymerization of n-butyl acrylate by reverse iodine transfer polymerization[J]. ACS Symposium, 2006, 944( 3): 281- 282.
38	LACROIX-DESMAZES P, TONNAR J, BOUTEVIN B. Reverse iodine transfer polymerization (RITP) in emulsion[J]. Macromolecular Symposia, 2007, 248( 1): 150- 157.
39	GOTO A, NAGASAWA K, SHINJO A, et al. Reversible chain transfer catalyzed polymerization of methyl methacrylate with in-situ formed alkyl iodide initiator[J]. Australian Journal of Chemistry, 2009, 62: 1492- 1495.
40	LIU X, XU Q, ZHANG L, et al. Visible-light-induced living radical polymerization using in situ bromine-iodine transformation as an internal boost[J]. Polymer Chemistry, 2017, 8( 16): 2538- 2551.
41	XIAO L, SAKAKIBARA K, TSUJII Y, et al. Organocatalyzed living radical polymerization viain situ halogen exchange of alkyl bromides to alkyl iodides[J]. Macromolecules, 2017, 50( 5): 1882- 1891.
42	BAI L, ZHANG L, PAN J, et al. Developing a synthetic approach with thermoregulated phase-transfer catalysis: facile access to metal-mediated living radical polymerization of methyl methacrylate in aqueous/organic biphasic system[J]. Macromolecules, 2013, 46( 6): 2060- 2066.
43	PAN J, ZHANG L, BAI L, et al. Atom transfer radical polymerization of methyl methacrylate with a thermo-responsive ligand: construction of thermoregulated phase-transfer catalysis in an aqueous-organic biphasic system[J]. Polymer Chemistry, 2013, 4( 9): 2876.
44	DU X, PAN J, CHEN M, et al. Thermo-regulated phase separable catalysis (TPSC)-based atom transfer radical polymerization in a thermo-regulated ionic liquid[J]. Chem. Commun. (Camb), 2014, 50( 66): 9266- 9269.
45	DING M, JIANG X, PENG J, et al. Diffusion-regulated phase-transfer catalysis for atom transfer radical polymerization of methyl methacrylate in an aqueous/organic biphasic system[J]. Macromolecular Rapid Communications, 2015, 36( 6): 538- 546.
46	JIANG X, LIU Y, DING M, et al. AGET ATRP of methyl methacrylate based on thermoregulated phase transfer catalysis in organic/aqueous biphasic system: facile and highly efficient in situ catalyst/ligand separation and recycling[J]. Macromolecular Chemistry and Physics, 2015, 216( 11): 1171- 1179.
47	ZHANG B, JIANG X, ZHANG L, et al. Fe(Ⅲ)-mediated ICAR ATRP in a p-xylene/PEG-200 biphasic system: facile and highly efficient separation and recycling of an iron catalyst[J]. Polymer Chemistry, 2015, 6( 37): 6616- 6622.
48	MIYAKE G M, THERIOT J C. Perylene as an organic photocatalyst for the radical polymerization of functionalized vinyl monomers through oxidative quenching with alkyl bromides and visible light[J]. Macromolecules, 2014, 47( 23): 8255- 8261.
49	TREAT N J, SPRAFKE H, KRAMER J W, et al. Metal-free atom transfer radical polymerization[J]. Journal of the American Chemistry Society, 2014, 136( 45): 16096- 16101.
50	OGAWA K A, GOETZ A E, BOYDSTON A J. Metal-free ring-opening metathesis polymerization[J]. Journal of the American Chemistry Society, 2015, 137( 4): 1400- 1403.
51	PAN X, LAMSON M, YAN J, et al. Photoinduced metal-free atom transfer radical polymerization of acrylonitrile[J]. ACS Macro. Letters, 2015, 4( 2): 192- 196.
52	LIU X D, ZHANG L, CHENG Z P, et al. Catalyst-free iodine-mediated living radical polymerization under irradiation over a wide visible-light spectral scope[J]. Polymer Chemistry, 2016, 7( 21): 3576- 3588.
53	LIU X, ZHANG L, CHENG Z, et al. Straightforward catalyst/solvent-free iodine-mediated living radical polymerization of functional monomers driven by visible light irradiation[J]. Chem. Commun. (Camb), 2016, 52( 72): 10850- 10853.
54	NI Y, TIAN C, ZHANG L, et al. Photocontrolled iodine-mediated green reversible-deactivation radical polymerization of methacrylates: effect of water in the polymerization system[J]. ACS Macro Letters, 2019, 8( 11): 1419- 1425.
55	OHTSUKI A, LEI L, TANISHIMA M, et al. Photocontrolled organocatalyzed living radical polymerization feasible over a wide range of wavelengths[J]. Journal of American Chemistry Society, 2015, 137( 16): 5610- 5617.
56	BARKER I A, DOVE A P. Triarylsulfonium hexafluorophosphate salts as photoactivated acidic catalysts for ring-opening polymerisation[J]. Chem. Commun. (Camb), 2013, 49( 12): 1205- 1207.
57	RUBIO A, DESNOS G, SEMSARILAR M. Nanostructured membranes from soft and hard nanoparticles prepared via RAFT-mediated PISA[J]. Macromolecular Chemistry and Physics, 2018, 219( 20): 1800351.
58	COUTURAUD B, GEORGIOU P G, VARLAS S, et al. Poly(pentafluorophenyl methacrylate)-based nano-objects developed by photo-PISA as scaffolds for post-polymerization functionalization[J]. Macromol Rapid Commun, 2019, 40( 2): e1800460.
59	MELLOT G, BEAUNIER P, GUIGNER J M, et al. Beyond simple ab diblock copolymers: application of bifunctional and trifunctional RAFT agents to PISA in water[J]. Macromol. Rapid Commun., 2019, 40( 2): e1800315.
60	YAO X, PENG R, DING J. Cell-material interactions revealed via material techniques of surface patterning[J]. Adv. Mater., 2013, 25( 37): 5257- 5286.
61	DURAND N, AMEDURI B, BOUTEVIN B. Synthesis and characterization of functional fluorinated telomers[J]. Journal of Polymer Science Part A: Polymer Chemistry, 2011, 49( 1): 82- 92.
62	WANG C G, CHEN C, SAKAKIBARA K, et al. Facile fabrication of concentrated polymer brushes with complex patterning by photocontrolled organocatalyzed living radical polymerization[J]. Angew. Chem. Int. Ed. Engl., 2018, 57( 41): 13504- 13508.
63	SARKAR J, XIAO L, JACKSON A W, et al. Synthesis of transition-metal-free and sulfur-free nanoparticles and nanocapsules via reversible complexation mediated polymerization (RCMP) and polymerization induced self-assembly (PISA)[J]. Polymer Chemistry, 2018, 9( 39): 4900- 4907.
64	WANG G, SCHMITT M, WANG Z, et al. Polymerization-induced self-assembly (PISA) using ICAR ATRP at low catalyst concentration[J]. Macromolecules, 2016, 49( 22): 8605- 8615.
65	WANG G, WANG Z, LEE B, et al. Polymerization-induced self-assembly of acrylonitrile via ICAR ATRP[J]. Polymer, 2017, 129: 57- 67.
66	CAO M, ZHANG Y, WANG J, et al. ICAR ATRP polymerization-induced self-assembly using a mixture of macroinitiator/stabilizer with different molecular weights[J]. Macromol. Rapid Commun., 2019, 40( 20): e1900296.
67	CHEN L, LI P, LU X, et al. Binary polymer brush patterns from facile initiator stickiness for cell culturing[J]. Faraday Discuss, 2019, 219: 189- 202.
68	WANG J, WU Z, WANG G, et al. In situ crosslinking of nanoparticles in polymerization-induced self-assembly via arget ATRP of glycidyl methacrylate[J]. Macromol. Rapid Commun., 2019, 40( 2): e1800332.
69	XU Q, TIAN C, ZHANG L, et al. Photo-controlled polymerization-induced self-assembly (Photo-PISA): a novel strategy using in situ bromine-iodine transformation living radical polymerization[J]. Macromol. Rapid Commun., 2019, 40( 2): e1800327.

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