Photoredox catalyst-mediated atom transfer radical addition for polymer functionalization under visible light

Xu, Jiangtao; Atme, Amir; Martins, Ana Flavia Marques; Jung, Kenward; Boyer, Cyrille

doi:10.1039/c4py00193a

Cited by 40 publications

(42 citation statements)

References 49 publications

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“…To expand these approaches to particular applications where the reactions need to be conducted at low temperatures (e.g., polymerization of monomers with low ceiling temperatures or biochemical applications), 132 a photoinduced radical polymerization process becomes an excellent candidate. 83,[133][134][135] Many works have recently been reported in this field such as photo-ATRP 69,70,75,78,80,84,[86][87][88]110,132,[136][137][138][139][140][141][142][143][144][145][146][147][148][149][150][151][152][153] or photo-RAFT. [72][73][74]76,85, The CuCs-based PISs proposed so far are capable of initiating photo-ATRP.…”

Section: Copper Complexes As Photoinitiators Of Controlled Radical Pomentioning

confidence: 99%

“…fragmentation chain transfer polymerization (photo-RAFT). [72][73][74][75][76] Even though Ru-or Ir-based complexes exhibit excellent photoinitiation ability for polymerization reactions under visible lights, they are based on rare transition metals (Ru or Ir): it is highly interesting to develop metal-free compounds or low-cost metalbased complexes. Many metal-free compounds that have been proposed so far exhibit a high efficiency as PIs of polymerization under visible lights (see refs.…”

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confidence: 99%

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Copper and iron complexes as visible‐light‐sensitive photoinitiators of polymerization

Xiao

Zhang

Campolo

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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International audienceThe utilization of visible lights for the fabrication of polymeric materials is recognized as a promising and environmentally friendly approach. This process relies on the photochemical generation of reactive species (e.g., radicals, radical cations, or cations) from well-designed photoinitiators (PIs) or photoinitiating systems (PISs) to initiate the polymerization reactions of different monomers (acrylates, methacrylates, epoxides, and vinyl ethers). In spite of the fact that metal complexes such as ruthenium- or iridium-based complexes have found applications in organic and polymer synthesis, the search of other low-cost metal-based complexes as PISs is emerging and attracting increasing attentions. Particularly, the concept of the photoredox catalysis has appeared recently as a unique tool for polymer synthesis upon soft conditions (use of light emitting diodes and household lamp). This highlight focuses on recently designed copper and iron complexes as PI catalysts in the application of photoinduced polymerizations (radical, cationic, interpenetrated polymer networks, and thiol-ene) or controlled radical polymerization under visible light irradiatio

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Section: Copper Complexes As Photoinitiators Of Controlled Radical Pomentioning

confidence: 99%

mentioning

confidence: 99%

Copper and iron complexes as visible‐light‐sensitive photoinitiators of polymerization

Xiao

Zhang

Campolo

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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“…[33] These resultsi ndicatet hat the use of such am acroinitiator successfully initiates the chain-extension reaction. [34] However, the initiation efficiency of the macroinitiator is poor, as confirmed by decreased control of the molecular weight of the obtained products.T his might result from the impact of steric hindrance from the long polymer chain and the limited chain-endf unctionality, [35] leadingt oaloss of the living nature of the polymerizations.…”

Section: Entrymentioning

confidence: 99%

Visible‐Light‐Driven Hydrogen Production and Polymerization using Triarylboron‐Functionalized Iridium(III) Complexes

Yang

Yuan

et al. 2018

Chemistry An Asian Journal

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The development of novel iridium(III) complexes has continued as an important area of research owing to their highly tunable photophysical properties and versatile applications. In this report, three heteroleptic dimesitylboron-containing iridium(III) complexes, [Ir(p-B-ppy) (N^N)] {p-B-ppy=2-(4-dimesitylborylphenyl)pyridine; N^N=dipyrido[3,2-a:2',3'-c]phenazine (dppz) (1), dipyrido[3,2-d:2',3'-f]quinoxaline (dpq) (2), and 1,10-phenanthroline (phen) (3)}, were prepared and fully characterized electrochemically, photophysically, and computationally. Altering the conjugated length of the N^N ligands allowed us to tailor the photophysical properties of these complexes, especially their luminescence wavelength, which could be adjusted from λ=583 to 631 nm in CH Cl . All three complexes were evaluated as visible-light-absorbing sensitizers for the photogeneration of hydrogen from water and as photocatalysts for the photopolymerization of methyl methacrylate. The results showed that all of them were active in both photochemical reactions. High activity for the photosensitizer (over 1158 turnover numbers with 1) was observed, and the system generated hydrogen even after 20 h. Additionally, poly(methyl methacrylate) with a relatively narrow molecular-weight distribution was obtained if an initiator (i.e., ethyl α-bromophenylacetate) was used. The living character of the photoinduced polymerization was confirmed on the basis of successful chain-extension experiments.

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“…These last decades, controlled/living radical polymerization (CRP) has been the subject of intense efforts and great attention . More recently, the use of light in CRP has been introduced . The controlled radical photopolymerization (CRP2) benefits of different advantages compared with CRP, including a spatial and temporal control of the polymerization reaction but also the possibility to carry out the polymer synthesis at room temperature to avoid undesired side reactions.…”

Section: Introductionmentioning

confidence: 99%

Iron complexes as potential photocatalysts for controlled radical photopolymerizations: A tool for modifications and patterning of surfaces

Telitel

Dumur

Campolo

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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International audienceThis article reports on the presumably first use of iron complexes (FeC) as potential photocatalysts for controlled radical photopolymerization reactions (CRP2). Three compounds were designed and investigated. Good linear evolutions of the molecular weight (Mn) with the conversion were observed. A comparison was provided with a reference iridium (III) complex [Ir(ppy)3 where ppy stands for 2-phenylpyridine]. The on/off photopolymerization experiments highlight the presence of dormant species and a re-initiation on demand upon irradiation. This unique re-initiation property was used for the modification of surfaces (hydrophilic/hydrophobic properties) and surface patterning as well as the synthesis of a block co-polymer (PMMA-b-PBA). A comparative analysis of the behavior of these iron complexes in thermally and photochemically activated polymerization was provided. The chemical mechanisms were studied by steady state photolysis, laser flash photolysis, cyclic voltammetry, luminescence quenching, and electron spin resonance experiments. A catalytic cycle was proposed with two steps: (i) the oxidation of the FeC excited state by an alkyl halide and (ii) the reduction by the oxidized form (FeC°+) by an amine or the macroradicals leading to the regeneration of the catalyst

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Photoredox catalyst-mediated atom transfer radical addition for polymer functionalization under visible light

Abstract: A facile method for post-functionalization of polymers with side olefin groups was developed by visible light-mediated atom transfer radical addition (ATRA) employing a photoredox catalyst, fac-Ir(ppy)3.

Cited by 40 publications

References 49 publications

Copper and iron complexes as visible‐light‐sensitive photoinitiators of polymerization

Copper and iron complexes as visible‐light‐sensitive photoinitiators of polymerization

Visible‐Light‐Driven Hydrogen Production and Polymerization using Triarylboron‐Functionalized Iridium(III) Complexes

Iron complexes as potential photocatalysts for controlled radical photopolymerizations: A tool for modifications and patterning of surfaces

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