Self‐Healing Supramolecular Gels Formed by Crown Ether Based Host–Guest Interactions

Zhang, Mingming; Xu, Duanfu; Yan, Xuzhou; Chen, Jianzhuang; Dong, Shengyi; Zheng, Bo; Huang, Feihe

doi:10.1002/anie.201203063

Cited by 680 publications

(309 citation statements)

References 71 publications

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“…These properties can be utilized to introduce self-healing behavior in crown ether-based polymers [231]. In 2012, Huang and coworkers presented the first self-healing supramolecular gel with crown ether moieties [247]. For this purpose, poly(methyl methacrylate) containing dibenzo [24]crown-8 (DB24C8) was synthesized and crosslinked with two bis-(ammonium salts) having different end-group sizes (Fig.…”

Section: Self-healing Polymers Based On Reversible Host-guest Interacmentioning

confidence: 99%

“…The host-guest interactions were proven by 1 H NMR Fig. 20 Supramolecular gels based on crown ether interactions [247] spectroscopy, indicating a chemical shift for the aromatic protons after complexation. Moreover, the gels are degradable, triggered by pH stimuli; for example, addition of a base causes deprotonation of the amines, resulting in disintegration of host and guest.…”

Section: Self-healing Polymers Based On Reversible Host-guest Interacmentioning

confidence: 99%

See 1 more Smart Citation

Intrinsic Self-Healing Polymers Based on Supramolecular Interactions: State of the Art and Future Directions

Enke

Döhler

Bode

et al. 2015

Self-Healing Materials

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Supramolecular polymers are an intriguing class of materials with dynamic behavior as a result of the presence of non-covalent bonds. These bonds include hydrogen bonds, metallopolymers, ionomers, host-guest as well as π-π interactions. The strength of these supramolecular bonds can be tuned by varying the binding motifs. Their reversible and dynamic character can be utilized to engineer self-healing polymers. This review briefly presents the preconditions for design of self-healing polymers and summarizes the development of supramolecular self-healing polymers based on various non-covalent interactions. Furthermore, challenges and perspectives for the understanding of self-healing mechanisms and the preparation of novel materials with enhanced properties are discussed.

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Section: Self-healing Polymers Based On Reversible Host-guest Interacmentioning

confidence: 99%

Section: Self-healing Polymers Based On Reversible Host-guest Interacmentioning

confidence: 99%

Intrinsic Self-Healing Polymers Based on Supramolecular Interactions: State of the Art and Future Directions

Enke

Döhler

Bode

et al. 2015

Self-Healing Materials

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“…This was nicely explored by Huang and co-workers who reported an influential example of a self-healing gel, 46 formed as a consequence of supramolecular cross-linking of a dibenzo-24-crown-8-functionalised polymer with ditopic bisammonium 80 crosslinkers. Non-covalent interactions between the crosslinker and the polymer converted the system from a sol to a gel, with the size of the ammonium cation appearing to control the kinetics of assembly process (the larger cation formed gels much more slowly).…”

Section: Healable and Self-healing Materialsmentioning

confidence: 99%

Supramolecular materials

2017

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“…[9][10][11][12][13][14][15][16][17][18] Having the potential to repair the damage caused by mechanical use over time, these polymeric materials are, and will be, highly sought-aer due to considerations for safety, extended use period and energy conservation. [19][20][21][22][23][24] In general, tiny fractures or defects on the surface of the polymeric materials are difficult to correct, but the self-healing property offers a great advantage in this regard, extending the functional use period signicantly.…”

Section: -8mentioning

confidence: 99%

BODIPY based self-healing fluorescent gel formation via acylhydrazone linkage

Özdemir

Sözmen

2016

RSC Adv.

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Polymeric BODIPY derivatives with reactive functional groups undergo reversible formation of covalent bonds leading to self-healing properties. Cross-reactivity of acyl-hydrazine and aldehyde moieties forms the basis of dynamic covalent chemistry leading to sol-gel transition in this series of compounds. In addition, thin layers of absorbers show efficient energy transfer indicating a potential in solar concentration.Self-healing is a very intriguing emergent property which was until recently kept in the domain of biological systems. 1-8Reversible supramolecular interactions and certain covalent transformations which are also reversible under ambient conditions provided an avenue for the realization of self-healing with non-biological smart materials.9-18 Having the potential to repair the damage caused by mechanical use over time, these polymeric materials are, and will be, highly sought-aer due to considerations for safety, extended use period and energy conservation.19-24 In general, tiny fractures or defects on the surface of the polymeric materials are difficult to correct, but the self-healing property offers a great advantage in this regard, extending the functional use period signicantly.25 Judiciously engineered covalent interactions have the potential to result in particularly robust materials with such self-healing capability. Any tear or break in the material will leave behind multiple adhesive/cross-reactive termini, which, on contact, would reinstate the covalent bonds ruptured by the physical effector in the rst place. Cross-linked covalent polymers with self-healing properties are expected to result in particularly durable materials. 26-35During the past decade, the progress made in BODIPY chemistry has attracted considerable attention due to their high quantum yields, ease of derivatization and a multitude of potential applications. 36-42In this study, our goal was to combine the two phenomena namely, through space energy transfer and self-healing ability, to open a new path towards a new generation of solar concentrators. We targeted the synthesis of two gels (G1 and G2), which are to function as energy donor and acceptor layers. To that end, a BODIPY donor monomer M1 with triformyl groups and a BODIPY acceptor monomer M2 were separately synthesized.For the synthesis of M1, rstly triiodo-BODIPY derivative (compound 6) was synthesized and then 4-ethynyl benzaldehyde groups were attached this compound via Sonogashira coupling. The synthesis for the second monomer M2 started with the reaction of known BODIPY dye (compound 2) with 4-(hydroxymethyl) benzaldehyde under Knoevenagel conditions (Scheme 1). Thus, the monomer M2 was designed to have longer absorption and emission wavelengths, compared to the monomer M1 due to extended of conjugation and strong intramolecular charge transfer (ICT) (ESI, † Table S1). M2 was obtained via subsequent formylation with Dess-Martin periodianane. Following that conversion, a bis-acylhydrazine functionalized PEO polymer P1 (polyethyleneoxide, M n ¼ 2000) was pr...

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Self‐Healing Supramolecular Gels Formed by Crown Ether Based Host–Guest Interactions

Cited by 680 publications

References 71 publications

Intrinsic Self-Healing Polymers Based on Supramolecular Interactions: State of the Art and Future Directions

Intrinsic Self-Healing Polymers Based on Supramolecular Interactions: State of the Art and Future Directions

Supramolecular materials

BODIPY based self-healing fluorescent gel formation via acylhydrazone linkage

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