Visible Light Controlled Polymerization of Azide‐Derived Monomers: A Facile, Metal‐Free PET‐ATRP Route to Construct Azide Polymers

Ni, Bangqing; Wang, Danke; Hen, Zhang; Li, Pengqi; Niu, Tengfei

doi:10.1002/macp.201800529

Cited by 4 publications

(6 citation statements)

References 45 publications

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“…Using FT-IR, these authors demonstrated the presence of the desired azide functionality within the product polymer, supporting the tolerance of this method to these functional groups. 173 In other work, researchers disclosed the polymerization of 2-([4,6-dichloro-triazin-2-yl]oxy)ethyl methacrylate, 94 pyrenyl methacrylate, 94 and even fluorescein-o-methacrylate. 174 In addition, several bifunctional monomers have been reported in O-ATRP, such as allyl methacrylate, 171 methacrylate-based inimers (monomers that can also serve as initiators), 175 and dimethacrylate monomers to achieve polymer cross-linking.…”

Section: Methacrylatesmentioning

confidence: 99%

“…In all three cases, polymerizations were performed with 20 mol % of the methacrylate and gave moderate polymerization control (Đ ∼ 1.3−1.4), although the methacrylate content in the product polymer ranged from 25% (ethyl vinyl ether) to 67% (itaconic acid). 173 In another example, Chen and co-workers synthesized statistical copolymers of acrylonitrile (95 mol %) and itaconic acid (5 mol %), which showed good polymerization control (M n = 74 kDa, Đ = 1.2). However, only one example of this polymerization was reported, after which this system was not investigated further.…”

Section: Other Monomersmentioning

confidence: 99%

“…In 2019, Ni and Niu reported the successful polymerization of several azide containing methacrylates with good polymerization control ( M n = 11.9–22.6 kDa, Đ = 1.2–1.3, I * = 70% to 100%). Using FT-IR, these authors demonstrated the presence of the desired azide functionality within the product polymer, supporting the tolerance of this method to these functional groups …”

Section: Monomers Polymerized By O-atrpmentioning

confidence: 99%

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Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

2021

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The development of photoinduced organocatalyzed atom transfer radical polymerization (O-ATRP) has received considerable attention since its introduction in 2014. Expanding on many of the advantages of traditional ATRP, O-ATRP allows well-defined polymers to be produced under mild reaction conditions using organic photoredox catalysts. As a result, O-ATRP has opened access to a range of sensitive applications where the use of a metal catalyst could be of concern, such as electronics, certain biological applications, and the polymerization of coordinating monomers. However, key limitations of this method remain and necessitate further investigation to continue the development of this field. As such, this review details the achievements made to-date as well as future research directions that will continue to expand the capabilities and application landscape of O-ATRP. CONTENTS 4.5. Styrene and 4-Vinylpyridine 4.6. Vinyl Cyclopropanes 4.7. Other Monomers 5. Applications of O-ATRP 5.1. Synthesis of Block Copolymers 5.2. Synthesis of Graft Polymers 5.3. Synthesis of Hyperbranched Polymers 5.4. Synthesis of Star Polymers 5.5. Surface-initiated O-ATRP 5.6. Synthesis of Polymers in Continuous Flow 5.7. Metal Sensitive Applications of O-ATRP 6. Conclusions and Future Directions Author Information Corresponding Author Author Notes Biographies Acknowledgments References

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Section: Methacrylatesmentioning

confidence: 99%

Section: Other Monomersmentioning

confidence: 99%

Section: Monomers Polymerized By O-atrpmentioning

confidence: 99%

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Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

2021

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“…47 As a result of our inability to control polymerization using RAFT, synthesis of 2 was attempted using ATRP. Others have recently demonstrated the controlled synthesis of block copolymers with an aryl azide backbone or aryl azide initiator using ATRP methodology, 64,65 but to the best of our knowledge there have been no reports on the synthesis of self-immolative aryl azides and use in stimuli-responsive polymer backbones. For ATRP synthesis of 2, polyethylene glycol (PEG) macroinitiator (mPEG-Br) 6 was first synthesized using a literature procedure, 66 and reacted with methacrylate 4 under various ATRP conditions ( Table 2, Entries 1-6).…”

Section: Synthesismentioning

confidence: 99%

Synthesis and formulation of self‐immolative PEG‐aryl azide block copolymers and click‐to‐release reactivity with trans‐cyclooctene

Dadhwal

Lee

Goswami

et al. 2021

Journal of Polymer Science

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Self-immolative aryl azides can react with trans-cyclooctenes (TCO), triphenylphosphines or hydrogen sulfide (H 2 S) to activate prodrugs, imaging probes and drug delivery systems. To date, the synthesis of polymers containing these aryl azide self-immolative linkers and their reactivity with a strained alkene (i.e., in a bioorthogonal reaction) has not been explored. Also, due to the instability of aryl azides towards light and high temperatures, the polymerization methods compatible with aryl azides are limited. Through systematic investigation of the reversible addition-fragmentation chain transfer (RAFT) and atom transfer radical polymerization (ATRP) methods, a self-immolative PEG-aryl azide block copolymer (PEG 45-b-ABOC 28 2) and a non-responsive 4-fluoroaryl block copolymer (PEG 45-b-FBOC 24 3) was prepared. ATRP provided the desired polymers in a highly controlled manner, whereas the RAFT conditions led to higher levels of aryl azide polymer degradation. The ATRP derived polymers 2 and 3 were formulated into nanoparticles of approximately 200 nm diameter, and particle triggering was demonstrated by the [3+2]cycloaddition reaction of TCO with PEG 45-b-ABOC 28 2 in solution (pure polymer) and as a formulated nanoparticle. Preliminary in vitro cell viability studies suggested that the stimuli-responsive aryl azide polymers/nanoparticles are not cytotoxic up to 200 μg/ml concentrations.

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“…Polymers containing azido functionality either at the chain end(s) or as pendant groups have attracted a great deal of attention as azido group is capable of undergoing the celebrated CuAAC click reaction, thus allowing access to modified polymers . With regard to step‐growth polymers, both postfunctionalization and functional monomer approaches have been put to use to obtain a range of azido‐functionalized aliphatic and aromatic polymers.…”

Section: Introductionmentioning

confidence: 99%

A new cardo bisphenol monomer containing pendant azido group and the resulting aromatic polyesters

Maher

Nagane

Jadhav

et al. 2019

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

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Expanding on our strategy to synthesize aromatic stepgrowth polymers containing pendant clickable azido groups via functional monomer approach, we have now designed and synthesized a new cardo bisphenol, viz., 2-(2-azidoethyl)-3, 3-bis(4-hydroxyphenyl) isoindolin-1-one (PPH-N 3 ). PPH-N 3 was conveniently synthesized starting from commercially available phenolphthalein by a three-step route in an overall yield of 65% using simple organic transformations. Aromatic (co)polyesters bearing pendant azido groups were synthesized by low-temperature solution polycondensation of PPH-N 3 or different molar ratios of PPH-N 3 and bisphenol-A (BPA) with aromatic diacid chlorides in dry dichloromethane in the presence of triethylamine (TEA) as a base. The formation of medium to reasonably high-molecular-weight (co)polyesters was evidenced from intrinsic viscosity and number-average molecular-weight measurements that were in the range 0.52-0.85 dL/g and 16,700-28,200, respectively. Tough, transparent, and flexible films could be cast from chloroform solutions of these (co)polyesters. (Co)polyesters were characterized using FTIR, 1 H NMR, 13 C NMR spectroscopy, XRD, and TGA. The thermal curing reaction of (co)polyesters involving decomposition of azido groups was studied by DSC analysis. The chemical modification of a representative copolyester containing pendant azido groups was carried out quantitatively using catalyst-free azide-maleimide cycloaddition reaction with two maleimides, namely, Nmethylmaleimide and N-hexylmaleimide.Additional supporting information may be found in the online version of this article.

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Visible Light Controlled Polymerization of Azide‐Derived Monomers: A Facile, Metal‐Free PET‐ATRP Route to Construct Azide Polymers

Cited by 4 publications

References 45 publications

Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

Synthesis and formulation of self‐immolative PEG‐aryl azide block copolymers and click‐to‐release reactivity with trans‐cyclooctene

A new cardo bisphenol monomer containing pendant azido group and the resulting aromatic polyesters

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