Towards the Generation of Self‐Healing Materials by Means of a Reversible Photo‐induced Approach

Froimowicz, Pablo; Frey, Holger; Landfester, Katharina

doi:10.1002/marc.201000643

Cited by 202 publications

(137 citation statements)

References 32 publications

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“…One approach to recognize lighttriggered self-healing materials is to disperse immobilized photo-reactive moieties in polymers in which photo-crosslinking reactions are responsible for the healing of cracks. Froimowicz et al reported a self-healing hydrogel film by exploiting reversible photo-induced dimerization of anthracene on a dendritic polymer scaffold [83]. Recovery of the film was observed overnight after two treatments of UV light (254 nm as the first treatment and 366 nm as the second treatment).…”

Section: Self-healing Materials With Optical-responsive Propertiesmentioning

confidence: 99%

Functional self-healing materials and their potential applications in biomedical engineering

Chen

Huang

et al. 2017

Adv Compos Hybrid Mater

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With the development of smart materials, stimulus-responsive self-repairing materials attract more and more research attention. Although self-healing materials including concretes, rubbers, and hydrogels have been extensively investigated in the past decades, novel functionalities or properties such as shape memory, sol-gel transition, adhesion, anti-biofouling, and electronic/magnetic property have been introduced to self-repairing systems in recent years in order to broaden the scope of their applications in energy, drug delivery, tissue adhesion, cell culture, etc. In this paper, we first present an overview of the general strategies to prepare self-healing materials and the characterization methods to assess their healing performance. Then, we mainly focus on reviewing recent progress in novel self-healing materials possessing unique functionalities and their potential applications in biomedical engineering. Finally, the challenges and scope for future development are also discussed.

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Section: Self-healing Materials With Optical-responsive Propertiesmentioning

confidence: 99%

Functional self-healing materials and their potential applications in biomedical engineering

Chen

Huang

et al. 2017

Adv Compos Hybrid Mater

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“…195,225,318 Incorporation of these into hydrophilic polymers or dendrimers was recently shown to enable the formation of hydrogels upon irradiation induced crosslinking. 319 Such light-sensitive materials exhibit highly interesting self-healable properties. 196,224,[319][320] Transferring this concept to microgels containing cinnamoyl groups on the surface is assumed to give rise to the light-induced formation of macroscopic hydrogels by interparticular crosslinking upon photo-dimerization.…”

Section: Surface Modification Of Phema and P(hema-co-maa) Microgels Wmentioning

confidence: 99%

“…319 Such light-sensitive materials exhibit highly interesting self-healable properties. 196,224,[319][320] Transferring this concept to microgels containing cinnamoyl groups on the surface is assumed to give rise to the light-induced formation of macroscopic hydrogels by interparticular crosslinking upon photo-dimerization. Primarily, the successful functionalization of microgels with cinnamoyl groups has to be achieved.…”

Section: Surface Modification Of Phema and P(hema-co-maa) Microgels Wmentioning

confidence: 99%

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

Klinger

2013

Springer Theses

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This thesis focuses on the design, synthesis and characterization of novel photo-sensitive microgels and nanoparticles as potential materials for the loading and light-triggered release/accessibility of functional compounds. In order to realize this concept, different approaches to irradiation-dependent response mechanisms have been investigated.Novel light-cleavable divinyl functionalized monomeric crosslinkers based on o-nitrobenzyl derivatives were synthesized and used for the preparation of either PMMA or hydroxyl functionalized PHEMA microgels swellable and degradable in organic solvents. By the introduction of anionic MAA moieties into the PHEMA microgels, this concept was successfully transferred to double stimuli-responsive p(HEMA-co-MAA) hydrogel nanoparticles exhibiting a pH-dependent swelling and light-induced degradation behavior in aqueous media. This sensitivity to two orthogonal triggers is proposed to combine a pHinduced post-formation loading mechanism with a pH-and light-triggered release. In addition, a new class of enzyme-and light-sensitive PAAm microgels based on (meth-)acrylate functionalized dextrans as photo-and enzymatically degradable macromolecular crosslinkers was developed by introducing a photo-labile linker between the enzymatically degradable dextran chain and the polymerizable vinyl moieties. Here, the water solubility of the crosslinkers is assumed to enable an in situ loading approach of hydrophilic compounds.A different approach to the loading of microgels is based on photo-labile covalent microgel-drug conjugates. The first step to the realization of this concept was achieved by the development of a novel functional monomer consisting of a doxorubicin molecule covalently attached to a radically polymerizable methacrylate group via a photo-cleavable linker.Moreover, in order to enable the release of hydrophobic substances in aqueous media, hydrophobic nanoparticles consisting of a photo-resist polymer were designed to be degradable upon irradiation in water. Light-triggered conversion of the initial hydrophobic polymer into hydrophilic PMAA induced in situ particle dissolution and release of nile red.Since the introduction of a stimuli-responsive shell around a microgel is assumed to prevent leakage of embedded compounds, studies on non-stimuli-responsive shell formation around preformed microgel seed particles and the formation of microgel cores in polymeric shells were conducted to investigate potential synthetic pathways to this approach.In a last attempt, the surface of PHEMA and p(HEMA-co-MAA) microgels was functionalized with cinnamoyl groups in order to trigger the (reversible) particles interaction with each other by light-induced [2+2] cycloaddition reactions.

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“…12,13 Although various applications including photolithography 9 and the fabrication of liquid crystals 14 have been examined, there are only a few reports on photoinduced mendable materials using photodimerization. 15,16 Chung et al 15 developed a photomendable polymer using cinnamate dimer. A double network polymer was synthesized through the simultaneous processes of photoinduced radical polymerization of methacrylate monomers and photodimerization of the cinnamoyl groups in 1,1,1-tris-(cinnamoyloxymethyl) ethane.…”

Section: Introductionmentioning

confidence: 99%

“…Cracks in this polymer were repaired with 280 nm irradiation, which promoted the recovery of the 1,1,1-tris-(cinnamoyloxymethyl) ethane-based network structure. Froimwicz et al 16 presented a photomendable hyper-branched polymer based on anthracene dimers. The surface scratches of this polymer were mended in two steps.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced mendable network polymer from poly(butylene adipate) end-functionalized with cinnamoyl groups

Oya

Sukarsaatmadja

Ishida

et al. 2012

Polym J

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A network polymer with photoinduced mending abilities was prepared from cinnamoyl-telechelic prepolymer of poly(butylene adipate), PBAC 2 , and a tetra-cinnamoyl linker, C 4 , by photodimerization. The photodimerization reaction of the cinnamoyl groups was analyzed using both ultraviolet (UV)/visible (vis) and infrared (IR) spectroscopy. In the reaction, the isomerization of the cinnamate group from the trans to the cis conformation competes with the dimerization reaction of cinnamates. The fractions of dimer and isomer populations estimated from the UV/vis spectra revealed that dimerization was the more preferred reaction at temperatures higher than the melting point of PBAC 2 . When a film of the network polymer was damaged by tapping, the cinnamate dimers dissociated to form cinnamate monomers due to the reversibility of the dimerization. To recover the network structure, these monomers could be dimerized once again through a photoirradiation process. These results show that cracks in the network polymer can be recovered through photoirradiation.

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Towards the Generation of Self‐Healing Materials by Means of a Reversible Photo‐induced Approach

Cited by 202 publications

References 32 publications

Functional self-healing materials and their potential applications in biomedical engineering

Functional self-healing materials and their potential applications in biomedical engineering

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

Photoinduced mendable network polymer from poly(butylene adipate) end-functionalized with cinnamoyl groups

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