Polymerization-induced emission (PIE) of multifunctional polyamides synthesized by Ugi polymerization and targeted imaging of lysosomes

Meng, Xue; Hao, Tingting; Zhang, Da; Zhao, Rong Hui; Yiu, Hongmei; zhang, peng fei; Deng, Kui Lin

doi:10.1039/d2tb02639b

“…110 112 Deng et al prepared a series of polyamide derivatives (PAMs) containing pendent morpholine groups, which endow polymerization-induced emission, and applied them to target imaging trackers and as real-time monitors of changes of Fe 3+ concentration in lysosomes. 113 Tomalia, Klajnert-Maculewicz et al showed that a functionalized PAMAM dendrimer forms a polyplex with double stranded DNA and is nontoxic for HeLa and HMEC-1 cells up to a concentration of 10 mg/mL. The unique intrinsic luminescence properties of the dendrimer revealed that it accumulates in endosomal compartments.…”

Section: Room-temperature Phosphorescence (Rtp)mentioning

confidence: 99%

“…Ding et al investigated peptidomimetic polyurea derivatives with AIE characteristics for conformation-assisted deformation, discoloration, and intracellular drug delivery with effective cancer theranosis in vitro and in vivo . Deng et al prepared a series of polyamide derivatives (PAMs) containing pendent morpholine groups, which endow polymerization-induced emission, and applied them to target imaging trackers and as real-time monitors of changes of Fe 3+ concentration in lysosomes . Tomalia, Klajnert-Maculewicz et al showed that a functionalized PAMAM dendrimer forms a polyplex with double stranded DNA and is nontoxic for HeLa and HMEC-1 cells up to a concentration of 10 mg/mL.…”

Section: Macromolecules With Nonconventional Luminescencementioning

confidence: 99%

Recent Progress in Nonconventional Luminescent Macromolecules and their Applications

Jiang,

Zhu,

Li

et al. 2024

Macromolecules

5

0

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Water‐Involved Carbon‐Nitrogen Triple‐Bond Monomer Based Polymerization toward Processable Functional Polyamides under Ambient Conditions

Li,

Jing,

Xia

et al. 2024

Angewandte Chemie

0

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Polyamide plays a pivotal role in engineering thermoplastics. Constrained by the harsh conditions and arduous procedures for its industrial synthesis, developing facile synthesis of polyamides is still challengeable and holds profound significance. Herein, we successfully utilized water as one of the monomers to synthesize functional polyamides under ambient conditions. A powerful multicomponent polymerization of water, isocyanides, and chlorooximes was established in phosphate‐buffered saline. Soluble and thermally stable polyamides with high weight‐average molecular weights (up to 53900) were obtained in excellent yields (up to 95%). The polymerization exhibits unique polymerization‐induced emission characteristics, successfully converting non‐emissive monomers into unconventional emissive polymers. Notably, the resultant polyamides could undergo effective post‐modification via the hydroxyl‐yne click reaction. By incorporating various functional groups into the polyamide, its emission color could be fine‐tuned from blue to green and to red. Remarkably, the refractive index (n) of the polyamide at 589 nm could be increased from 1.6173 to 1.7227 and the Δn could be unprecedentedly as high as 0.1054 for non‐heavy atom‐containing polymers after post‐modification, and its micron‐thick films exhibited excellent transparency in the visible region. Thus, this work not only establishes a powerful polymerization toward novel polyamides but also opens up an avenue for their versatile functionalization.

show abstract

Water‐Involved Carbon‐Nitrogen Triple‐Bond Monomer Based Polymerization toward Processable Functional Polyamides under Ambient Conditions

Li,

Jing,

Xia

et al. 2024

Angew Chem Int Ed

0

View full text Add to dashboard Cite

Polyamide plays a pivotal role in engineering thermoplastics. Constrained by the harsh conditions and arduous procedures for its industrial synthesis, developing facile synthesis of polyamides is still challengeable and holds profound significance. Herein, we successfully utilized water as one of the monomers to synthesize functional polyamides under ambient conditions. A powerful multicomponent polymerization of water, isocyanides, and chlorooximes was established in phosphate‐buffered saline. Soluble and thermally stable polyamides with high weight‐average molecular weights (up to 53900) were obtained in excellent yields (up to 95%). The polymerization exhibits unique polymerization‐induced emission characteristics, successfully converting non‐emissive monomers into unconventional emissive polymers. Notably, the resultant polyamides could undergo effective post‐modification via the hydroxyl‐yne click reaction. By incorporating various functional groups into the polyamide, its emission color could be fine‐tuned from blue to green and to red. Remarkably, the refractive index (n) of the polyamide at 589 nm could be increased from 1.6173 to 1.7227 and the Δn could be unprecedentedly as high as 0.1054 for non‐heavy atom‐containing polymers after post‐modification, and its micron‐thick films exhibited excellent transparency in the visible region. Thus, this work not only establishes a powerful polymerization toward novel polyamides but also opens up an avenue for their versatile functionalization.

show abstract

Polymerization-induced emission (PIE) of multifunctional polyamides synthesized by Ugi polymerization and targeted imaging of lysosomes

Abstract: In this paper, a series of polyamide derivatives (PAMs) containing morpholine groups were prepared by Ugi polymerization from dialdehyde, diacid, N-(2-aminoethyl)-morpholine and isonitrile compounds as the novel multi-responsive fluorescent sensors....

Cited by 6 publications

References 45 publications

Recent Progress in Nonconventional Luminescent Macromolecules and their Applications

Recent Progress in Nonconventional Luminescent Macromolecules and their Applications

Water‐Involved Carbon‐Nitrogen Triple‐Bond Monomer Based Polymerization toward Processable Functional Polyamides under Ambient Conditions

Water‐Involved Carbon‐Nitrogen Triple‐Bond Monomer Based Polymerization toward Processable Functional Polyamides under Ambient Conditions

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