Synthesis of thiophene-containing acyclic alkoxyamine for nitroxide-mediated radical polymerization of acrylates and styrene

Chu, Ya-Fen; Han, Yu-Min; Chen, Wenhua; Chu, Yuan-Hua; Lin, Chien‐Chu; Huang, Yishen; Nakamura, Yasuyuki; Huang, Chih‐Feng

doi:10.1016/j.polymer.2021.124062

Cited by 4 publications

(1 citation statement)

References 56 publications

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“…56,57 Nowadays, ATRP is one of the most widely used methods in fundamental research, 58 application studies, 25,59 and industrial production. 60 Besides ATRP, two other CRPs, reversible addition-fragmentation chain transfer (RAFT) polymerization 9,61,62 and nitroxide-mediated radical polymerization (NMP), 8,63 are also extensively investigated. CRPs are one of the most potent platforms for obtaining specific macromolecules, including functional linear/branched polymers, periodic copolymers, block copolymers (BCPs), and conducting surface modifications.…”

Section: Introductionmentioning

confidence: 99%

Combinations (Є) among controlled/living polymerizations and utilizations of efficient chemical reactions for the synthesis of novel polymeric materials

Huang,

Ejeta,

Kuo

et al. 2023

Polym. Chem.

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Section: Introductionmentioning

confidence: 99%

Combinations (Є) among controlled/living polymerizations and utilizations of efficient chemical reactions for the synthesis of novel polymeric materials

Huang,

Ejeta,

Kuo

et al. 2023

Polym. Chem.

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α‐Hydrogen spirocyclic alkoxyamines synthesis: ESR verified Nitroxides generation and their potential application in NMP polymerization

Guerrero‐Caicedo,

Pardo‐Tamayo,

Romero

et al. 2023

ChemistrySelect

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Herein, we report a synthetic methodology towards the construction of new cylic alkoxyamines without the prior obtention of their respective nitroxides. These systems are constituted by an indene core connected to a pyrrolidine nucleus through a spiro carbon atom, containing an adjacent α‐hydrogen to the N atom, in order to exhibit the 1‐azaspiro[4.4]nonane frame. Alkoxyamines were synthesised by a free radical‐based spirocyclization, starting from functionalized oxime ethers, involving aryl and neutral alkoxyaminyl radicals in 16–40 % yields. Then, the novel spirocyclic aminoxyl radicals (nitroxides) were detected in ESR spectra, when alkoxyamines were subjected by the thermal homolytic cleavage of their −C−O−N− bond. In general, the temperatures found were in accordance with the increase in the stability of the carbon‐centred radical for the same type of nitroxides. In addition, a spirocyclic alkoxyamine 8 b with α‐hydrogen was employed as initiators/mediators in the styrene bulk homopolymerization, obtaining high conversions and relatively narrow dispersity (Ð~1.5). This suggests that the synthetic methodology used in this research work to obtain α‐hydrogen spirocyclic alkoxyamines would have the potential to be applied in nitroxide‐mediated polymerization (NMP).

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Energy transfer photocatalyst enabled by covalent organic framework induced reversible complexation-mediated polymerization under white LED light irradiation and the mechanism study

Zhao

Lü

et al. 2022

Materials Today Chemistry

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Synthesis of thiophene-containing acyclic alkoxyamine for nitroxide-mediated radical polymerization of acrylates and styrene

Cited by 4 publications

References 56 publications

Combinations (Є) among controlled/living polymerizations and utilizations of efficient chemical reactions for the synthesis of novel polymeric materials

Combinations (Є) among controlled/living polymerizations and utilizations of efficient chemical reactions for the synthesis of novel polymeric materials

α‐Hydrogen spirocyclic alkoxyamines synthesis: ESR verified Nitroxides generation and their potential application in NMP polymerization

Energy transfer photocatalyst enabled by covalent organic framework induced reversible complexation-mediated polymerization under white LED light irradiation and the mechanism study

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