Photodegradable and size-tunable single-chain nanoparticles prepared from a single main-chain coumarin-containing polymer precursor

Fan, Weizheng; Tong, Xia; Yan, Qiang; Fu, Shangyi; Zhao, Yue

doi:10.1039/c4cc06629d

Cited by 66 publications

(59 citation statements)

References 43 publications

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“…UV light‐induced cycloadditions often constitute an alternative, convenient, atom‐efficient reaction class for single‐chain folding that can be carried out quantitatively at ambient temperature without the need for any metal catalyst. A number of photoinduced reactions have been examined for SCNP formation, including the light‐induced Diels–Alder reaction (DA; strictly speaking, the photochemical provision of an ene or diene species, which subsequently under goes a rapid ambient temperature DA reaction), the photoinduced nitrile‐imine mediated tetrazole‐ene cycloaddition, the photodimerization of anthracene, as well as the photodimerization of coumarin . Light‐triggered protocols, especially at higher wavelengths, are particularly attractive if, during the self‐folding process, temperature‐sensitive molecules are to be included into the SCNP.…”

Section: Repeat Unit Folding: Latest Developmentsmentioning

confidence: 99%

Single‐Chain Folding of Synthetic Polymers: A Critical Update

Altintas

Barner‐Kowollik

2015

Macromol. Rapid Commun.

215

194

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The current contribution serves as a critical update to a previous feature article from us (Macromol. Rapid Commun. 2012, 33, 958−971), and highlights the latest advances in the preparation of single chain polymeric nanoparticles and initial—yet promising—attempts towards mimicking the structure of natural biomacromolecules via single‐chain folding of well‐defined linear polymers via so‐called single chain selective point folding and repeat unit folding. The contribution covers selected examples from the literature published up to ca. September 2015. Our aim is not to provide an exhaustive review but rather highlight a selection of new and exciting examples for single‐chain folding based on advanced macromolecular precision chemistry. Initially, the discussion focuses on the synthesis and characterization of single‐chain folded structures via selective point folding. The second part of the feature article addresses the folding of well‐defined single‐chain polymers by means of repeat unit folding. The current state of the art in the field of single‐chain folding indicates that repeat unit folding‐driven nanoparticle preparation is well‐advanced, while initial encouraging steps towards building selective point folding systems have been taken. In addition, a summary of the—in our view—open key questions is provided that may guide future biomimetic design efforts.

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Section: Repeat Unit Folding: Latest Developmentsmentioning

confidence: 99%

Single‐Chain Folding of Synthetic Polymers: A Critical Update

Altintas

Barner‐Kowollik

2015

Macromol. Rapid Commun.

215

194

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“…Especially, to achieve single‐chain folding via intramolecular noncovalent interaction is analogous to many folding process in nature, and it is envisaged as a simple pattern to mimic the behavior of biomacromolecules such as proteins, which exist in a well‐defined secondary, tertiary, and quaternary structure, resulting from accurate molecular weight, tacticity, monomer sequence, and so forth . Diverse crosslinking strategies, including covalent bonding, dynamic covalent bonding, and supramolecular interaction, have been adopted to achieve intramolecular collapsing. Especially, to prepare single‐chain nanoparticles via intramolecular noncovalent interaction is analogous to many folding process in nature and pave the way to understanding the behavior of biomacromolecules.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Nanoparticles via Single-Chain Folding Driven by Ferrous Ions

Wang

Jin

et al. 2016

Macromol. Rapid Commun.

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Single-chain nanoparticles can be obtained via single-chain folding assisted by intramolecular crosslinking reversibly or irreversibly. Single-chain folding is also an efficient route to simulate biomacromolecules. In present study, poly(N-hydroxyethylacrylamide-co-4'-(propoxy urethane ethyl acrylate)-2,2':6',2''-terpyridine) (P(HEAm-co-EMA-Tpy)) is synthesized via reversible addition fragmentation chain transfer polymerization. Single-chain folding and intramolecular crosslinking of P(HEAm-co-EMA-Tpy) are achieved via metal coordination chemistry. The intramolecular interaction is characterized on ultraviolet/visible spectrophotometer (UV-vis spectroscopy), proton nuclear magnetic resonance ((1)H NMR), and differential scanning calorimetry (DSC). The supramolecular crosslinking mediated by Fe(2+) plays an important role in the intramolecular collapsing of the single-chain and the formation of the nanoparticles. The size and morphology of the nanoparticles can be controlled reversibly via metal coordination chemistry, which can be characterized by dynamic light scattering (DLS), transmission electron microscope (TEM), and atomic force microscope (AFM).

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“…For the purpose of stabilization of the micellar aggregates prepared in a controlled manner we had introduced the photo crosslinkable coumarin derivative hymecromone. Coumarin is already well‐known as photo‐crosslinker for stabilization of polymeric particles such as micelles from amphiphilic copolymers . First, coumarin undergoes a dimerization performing a [2+2] photocycloaddition by UV‐light irradiation.…”

Section: Resultsmentioning

confidence: 99%

Size Tunable Core Crosslinked Micelles from HPMA‐Based Amphiphilic Block Copolymers

Krämer

Kim

Zentel

2017

Macro Chemistry & Physics

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A variety of core crosslinkable hydroxypropylmethacrylamide‐based block copolymers are synthesized by reversible addition‐fragmentation chain transfer (RAFT) polymerization, which are composed of hydroxypropyl‐methacrylate as hydrophilic block combined with a statistical hydrophobic block from laurylmethacrylate and the photo crosslinkable monomer. It is discovered that the self‐assembled micellar aggregates from these systems vary strongly in size depending not only on the velocity of the polarity switch (nanoprecipitation or slow dialysis) but also on the solvent from which they were dialyzed. In this way micellar aggregates with an Rh varying between 15 and 80 nm can be prepared from the same block copolymer. In addition, a new hydrophobic crosslinkable hymecromone moiety is introduced. In this way the differently sized nanoparticles can be effectively stabilized by photo‐crosslinking, leading to a high stability of the photo crosslinkable polymeric micelles against disintegration by detergents.

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Photodegradable and size-tunable single-chain nanoparticles prepared from a single main-chain coumarin-containing polymer precursor

Cited by 66 publications

References 43 publications

Single‐Chain Folding of Synthetic Polymers: A Critical Update

Single‐Chain Folding of Synthetic Polymers: A Critical Update

Supramolecular Nanoparticles via Single-Chain Folding Driven by Ferrous Ions

Size Tunable Core Crosslinked Micelles from HPMA‐Based Amphiphilic Block Copolymers

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