Cyclic Polymers with Pendent Carbazole Units: Enhanced Fluorescence and Redox Behavior

Zhu, Xing; Zhou, Nianchen; Zhang, Zhengbiao; Sun, Baoquan; Yang, Yonggang; Zhu, Jian; Zhu, Xiulin

doi:10.1002/anie.201101303

Cited by 93 publications

(80 citation statements)

References 45 publications

(21 reference statements)

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“…A series of combinations between CP and click reactions have been developed to successfully prepare cyclic polymers, such as atom transfer radical polymerization (ATRP)/coppercatalyzed azide-alkyne cycloaddition reaction (CuAAC) [8][9][10][11][12] , ATRP/UV-induced strain promoted azide-alkyne cycloaddition reaction (SPAAC) 13 , ATRP/ring-closing metathesis coupling 14,15 , ATRP/Diels-Alder reaction 16,17 , reversible addition-fragmentation chain transfer polymerization (RAFT)/CuAAC 18,19 , RAFT/thiol-ene reaction 20 ,…”

Section: Introductionmentioning

confidence: 99%

A ring-closure method for preparing cyclic polymers from unconjugated vinyl monomers

et al. 2015

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A unique ring-closure method was developed specifically focusing on the preparation of cyclic polymers derived from unconjugated vinyl monomers, which was established on the combination of reversible addition−fragmentaƟon chain transfer polymerization (RAFT)/macromolecular design via the interchange of xanthate (MADIX) and light-induced strain promoted azide-alkyne cycloaddition (SPAAC) reaction. By virtue of a specifically designed xanthate agent 1 as the reversible chain transfer agent to polymerize the unconjugated vinyl monomers, well-defined telechelic polymers were produced by RAFT/MADIX polymerization technique bearing the cyclopropenone-masked dibenzocyclooctyne and azide end groups. Under UV irradiation on a highly diluted solution of the resultant linear polymer precursors, the dibenzocyclooctyne end group was quantitatively released from cyclopropenone-masked dibenzocyclooctyne, which intramolecularly reacted with azide end group in situ to ring-close the linear polymers and produce the corresponding cyclic polymers based on the SPAAC click reaction. In addition, this novel ring-closure method produced the cyclic polymer chain with a cleavable S-C(S)O bond within the xanthate group, which facilitated the resultant cyclic polymers to be efficiently cleaved back to their linear counterparts under a mild aminolysis or reduction reaction condition.A unique ring-closure method was developed specifically focusing on the preparation of cyclic polymers derived from unconjugated vinyl monomers by combining RAFT/MADIX living polymerization technique and UV-induced SPAAC click reaction.

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Section: Introductionmentioning

confidence: 99%

A ring-closure method for preparing cyclic polymers from unconjugated vinyl monomers

et al. 2015

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“…It was first introduced to cyclic polymer chemistry by Laurent and Grayson in 2006 . Significant achievements have been made following the introduction, and plenty of cyclic polymers have since been reported . The click reaction has also been applied to construct multiring complex topologies from azide–alkyne multifunctional cyclic polymers .…”

Section: Generalization Of Existing Synthetic Stylesmentioning

confidence: 99%

“…Recently, cyclic poly(4‐vinylbenzyl)carbazole (PVBCZ) has been synthesized by successive combination of atom‐transfer radical polymerization and an intramolecular end‐to‐end click reaction . Cyclic PVBCZ displayed an enhanced fluorescence with a remarkably longer fluorescence life time in comparison with its linear counterpart.…”

Section: Potential Applications Of Cyclic Polymersmentioning

confidence: 99%

Advanced Developments in Cyclic Polymers: Synthesis, Applications, and Perspectives

Zhu

Hosmane

2015

ChemistryOpen

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Due to the topological effect, cyclic polymers demonstrate different and unique physical and biological properties in comparison with linear counterparts having the same molecular-weight range. With advanced synthetic and analytic technologies, cyclic polymers with different topologies, e.g. multicyclic polymers, have been reported and well characterized. For example, various cyclic DNA and related structures, such as cyclic duplexes, have been prepared conveniently by click chemistry. These types of DNA have increased resistance to enzymatic degradation and have high thermodynamic stability, and thus, have potential therapeutic applications. In addition, cyclic polymers have also been used to prepare organic–inorganic hybrids for applications in catalysis, e.g. catalyst supports. Due to developments in synthetic technology, highly pure cyclic polymers could now be produced in large scale. Therefore, we anticipate discovering more applications in the near future. Despite their promise, cyclic polymers are still less explored than linear polymers like polyolefins and polycarbonates, which are widely used in daily life. Some critical issues, including controlling the molecular weight and finding suitable applications, remain big challenges in the cyclic-polymer field. This review briefly summarizes the commonly used synthetic methodologies and focuses more on the attractive functional materials and their biological properties and potential applications.

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“…13, iii). Compared to living anionic polymerization techniques [182,183], CRP such as NMP [184], ATRP [185,186], and RAFT [187] polymerization are more attractive for the synthesis of linear polymer precursors for the unimolecular heterodifunctional approach. One significant advantage of this approach over the bimolecular homodifunctional coupling is that the complementary functionalities are tethered to each other, eliminating problems associated with inexact stoichiometries.…”

Section: Unimolecular Heterodifunctional Approachmentioning

confidence: 99%

“…One significant advantage of this approach over the bimolecular homodifunctional coupling is that the complementary functionalities are tethered to each other, eliminating problems associated with inexact stoichiometries. Later, a diverse number of cyclic (co)polymers, including cyclic poly(N-isopropylacrylamide) [180], poly(methyl acrylate-bstyrene) [188], poly(e-caprolactone) [189] and poly(4-vinylbenzyl-carbazole) [186], have been prepared in high purity via analogous approaches. Compared to the unimolecular homodifunctional approach, the effective concentration of reactive functional pairs on different chains is reduced by half, and this lowers the chance of oligomerization.…”

Section: Unimolecular Heterodifunctional Approachmentioning

confidence: 99%

Synthetic Strategies towards Well‐Defined Complex Polymeric Architectures through Covalent Chemistry

Ren

Qiao

2014

Chemie Ingenieur Technik

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Macromolecular architecture is a key factor determining the materials properties of polymers. Exploration of novel structural arrangements has become a viable means to develop advanced functional nanomaterials. Recent developments in polymer chemistry have forged robust synthetic platforms for innovative polymeric materials with highly regulated structures, functionalities, and compositions. This review summarizes the latest synthetic strategies for well-defined polymer architectures through covalent chemistry, with the focus on four main types of well-defined macromolecular constructs.

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Cyclic Polymers with Pendent Carbazole Units: Enhanced Fluorescence and Redox Behavior

Cited by 93 publications

References 45 publications

A ring-closure method for preparing cyclic polymers from unconjugated vinyl monomers

A ring-closure method for preparing cyclic polymers from unconjugated vinyl monomers

Advanced Developments in Cyclic Polymers: Synthesis, Applications, and Perspectives

Synthetic Strategies towards Well‐Defined Complex Polymeric Architectures through Covalent Chemistry

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