An acrylate AIE-active dye with a two-photon fluorescent switch for fluorescent nanoparticles by RAFT polymerization: synthesis, molecular structure and application in cell imaging

Huang, Zengfang; Chen, Yali; Wang, Runze; Zhou, Chaoyue; Liu, Xiaobo; Mao, Liucheng; Yuan, Jinying; Tao, Lei; Wei, Yen

doi:10.1039/c9ra10430e

Cited by 15 publications

(5 citation statements)

References 52 publications

(56 reference statements)

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“…These FPNs can also be produced from a wide range of monomers and impart greater stability compared to those nanoparticles formed from self-assembly, as FPNs prepared via self-assembly are often unstable in physiological solution due to the weak interactions among these amphiphilic fluorescent molecules. Similar studies have also been conducted by the same group and other groups on preparing AIE dyes via RAFT polymerization capable of self-assembly with similar characteristics since 2014 such as AIE crosslinkers, [87][88][89][90][91][92][93][94] AIE pendent groups with non-AIE monomers block copolymers, [95][96][97][98][99][100][101][102][103] AIE end-functionalized block copolymers, [48,49,[104][105][106][107] and AIE-functionalized monomers, [108][109][110][111][112][113][114][115][116][117][118][119] which helped to expand the library of AIE-functionalized polymers.…”

Section: Raft Aie Amphiphilic Block Copolymersmentioning

confidence: 56%

Aggregation-Induced Emission Polymers via Reversible-Deactivation Radical Polymerization

Teo

Fan

Ardana

et al. 2023

Preprint

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Aggregation-Induced Emission (AIE) is a unique phenomenon whereby aggregation of molecules induces fluorescence emission as opposed to the more commonly known Aggregation-Caused Quenching (ACQ). AIE has the potential to be utilized in the large-scale production of AIE-active polymeric materials because of their wide range of practical applications such as stimuli-responsive sensors, biological imaging agents, and drug delivery systems. This is evident from the increasing number of publications over the years since AIE was first discovered. In addition, the ever-growing interest in this field has led many researchers around the world to develop new and creative methods in the design of monomers, initiators and crosslinkers, with the goal of broadening the scope and utility of AIE polymers. One of the most promising approaches to the design and synthesis of AIE polymers is the use of the Reversible-Deactivation Radical Polymerization (RDRP) techniques, which enabled the production of well-controlled AIE materials that are often difficult to achieve by other methods. In this review, a summary of some recent works that utilize RDRP for AIE polymer design and synthesis is presented, including (1) the design of AIE-related monomers, initiators/crosslinkers; the achievements in preparation of AIE polymers using (2) Reversible Addition-Fragmentation Chain Transfer (RAFT) technique; (3) Atom Transfer Radical Polymerization (ATRP) technique; (4) other techniques such as Cu(0)-RDRP technique and Nitroxide-Mediated Polymerization (NMP) technique; (5) the possible applications of these AIE polymers and finally (6) a summary/perspective and the future direction of AIE polymers.

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Section: Raft Aie Amphiphilic Block Copolymersmentioning

confidence: 56%

Aggregation-Induced Emission Polymers via Reversible-Deactivation Radical Polymerization

Teo

Fan

Ardana

et al. 2023

Preprint

View full text Add to dashboard Cite

show abstract

“…These FPNs can also be produced from a wide range of monomers and impart greater stability compared to those nanoparticles formed from self-assembly, as FPNs prepared via self-assembly are often unstable in physiological solution due to the weak interactions among these amphiphilic fluorescent molecules. Similar studies have also been conducted by the same group and other groups on preparing AIE dyes via RAFT polymerization capable of self-assembly with similar characteristics since 2014 such as AIE crosslinkers, [89][90][91][92][93][94][95][96] AIE pendent groups with non-AIE monomers block copolymers, [97][98][99][100][101][102][103][104][105] AIE end-functionalized block copolymers, [51,52,[106][107][108][109] and AIEfunctionalized monomers, [110][111][112][113][114][115][116][117][118][119][120][121] which helped to expand the library of AIE-functionalized polymers.…”

Section: Aie Amphiphilic Polymers Via Raftmentioning

confidence: 80%

Aggregation‐induced emission polymers via reversible‐deactivation radical polymerization

Teo,

Fan,

Ardana

et al. 2023

Aggregate

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Aggregation‐induced emission (AIE) is a unique phenomenon whereby aggregation of molecules induces fluorescence emission as opposed to the more commonly known aggregation‐caused quenching (ACQ). AIE has the potential to be utilized in the large‐scale production of AIE‐active polymeric materials because of their wide range of practical applications such as stimuli‐responsive sensors, biological imaging agents, and drug delivery systems. This is evident from the increasing number of publications over the years since AIE was first discovered. In addition, the ever‐growing interest in this field has led many researchers around the world to develop new and creative methods in the design of monomers, initiators and crosslinkers, with the goal of broadening the scope and utility of AIE polymers. One of the most promising approaches to the design and synthesis of AIE polymers is the use of the reversible‐deactivation radical polymerization (RDRP) techniques, which enabled the production of well‐controlled AIE materials that are often difficult to achieve by other methods. In this review, a summary of some recent works that utilize RDRP for AIE polymer design and synthesis is presented, including (i) the design of AIE‐related monomers, initiators/crosslinkers; the achievements in preparation of AIE polymers using (ii) reversible addition–fragmentation chain transfer (RAFT) technique; (iii) atom transfer radical polymerization (ATRP) technique; (iv) other techniques such as Cu(0)‐RDRP technique and nitroxide‐mediated polymerization (NMP) technique; (v) the possible applications of these AIE polymers, and finally (vi) a summary/perspective and the future direction of AIE polymers.

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“…The development of non-conjugated polymers provides more possibilities for their applications in the biological field such as imaging, detection, trace analysis and so on. [25,26]…”

Section: Chemistryselectmentioning

confidence: 99%

“…In brief, the non‐conjugated AIE‐polymers can be directly prepared from the accessible non‐AIE monomers. The development of non‐conjugated polymers provides more possibilities for their applications in the biological field such as imaging, detection, trace analysis and so on [25,26] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Aggregation‐Induced Emission of Polyamide‐Amines as Fluorescent Switch Controlled by Hg²⁺‐Glutathione

et al. 2022

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In this study, a series of polyamide‐amines (PAAs) were prepared by Michael addition reaction of piperazine derivatives with N, N‐bisacrylamidepiperazine (BAP). An obvious aggregation‐induced emission (AIE) effect was observed for PAAs with fluorescence emission at 425–525 nm and affected by the structure, excitation wavelength, pH value, temperature, PAAs concentration and precipitant (acetone). The piperazine rings and amides groups on PAAs backbone contribute to their AIE by the clusterization‐triggered emission (CTE) mechanism, in accordance with the red‐shift of time‐dependent density functional theory (DFT). The DFT results proved the influence of packing way on aggregation luminescence, clarified the cluster mechanism of luminescences, and the ultraviolet absorption spectrum of PAAs. Additionally, based on the coordination, Hg2+ ions effectively quenched the fluorescence intensity of PAAs and showed enhanced quenching effect with the increase of concentration of Hg2+ ions. And also, a reducing agent, glutathione, can restore the fluorescence of PAAs solution mixed with Hg2+ ions, by which realizes the reversible switching process between fluorescence on and fluorescence off.

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An acrylate AIE-active dye with a two-photon fluorescent switch for fluorescent nanoparticles by RAFT polymerization: synthesis, molecular structure and application in cell imaging

Abstract: This work reported the synthesis of a novel acrylate AIE-active dye with a reversible two-photon fluorescent switch and its amphiphilic PEG-TM polymers via RAFT polymerization, which are attractive for applications in cell imaging.

Cited by 15 publications

References 52 publications

Aggregation-Induced Emission Polymers via Reversible-Deactivation Radical Polymerization

Aggregation-Induced Emission Polymers via Reversible-Deactivation Radical Polymerization

Aggregation‐induced emission polymers via reversible‐deactivation radical polymerization

Synthesis and Aggregation‐Induced Emission of Polyamide‐Amines as Fluorescent Switch Controlled by Hg²⁺‐Glutathione

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An acrylate AIE-active dye with a two-photon fluorescent switch for fluorescent nanoparticles by RAFT polymerization: synthesis, molecular structure and application in cell imaging

Abstract: This work reported the synthesis of a novel acrylate AIE-active dye with a reversible two-photon fluorescent switch and its amphiphilic PEG-TM polymers via RAFT polymerization, which are attractive for applications in cell imaging.

Cited by 15 publications

References 52 publications

Aggregation-Induced Emission Polymers via Reversible-Deactivation Radical Polymerization

Aggregation-Induced Emission Polymers via Reversible-Deactivation Radical Polymerization

Aggregation‐induced emission polymers via reversible‐deactivation radical polymerization

Synthesis and Aggregation‐Induced Emission of Polyamide‐Amines as Fluorescent Switch Controlled by Hg2+‐Glutathione

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Product

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Synthesis and Aggregation‐Induced Emission of Polyamide‐Amines as Fluorescent Switch Controlled by Hg²⁺‐Glutathione