Recent progress in self-healing polymers and hydrogels based on reversible dynamic B–O bonds: boronic/boronate esters, borax, and benzoxaborole

Cho, Seungwan; Hwang, Sung Yeon; Oh, Dongyeop X.; Park, Jeyoung

doi:10.1039/d1ta02308j

Cited by 224 publications

(158 citation statements)

References 134 publications

(138 reference statements)

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“…[49][50][51][52][53][54] Dynamic covalent bonds include Schiff base interactions, Diels−Alder interactions, and borate-ester and disulfide bonds. [55][56][57][58] Self-healing can also rely on physical molecular diffusion at the damaged interface. [59][60][61] In this case, the chemical nature, the chain length and molecular weight distribution as well as the mechanical properties of the polymer affect the diffusion speed and then the healing behavior.…”

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confidence: 99%

Recent Progress on Self‐Healable Conducting Polymers

Zhou

Sarkar

et al. 2022

Advanced Materials

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Materials able to regenerate after damage have been the object of investigation since the ancient times. For instance, self‐healing concretes, able to resist earthquakes, aging, weather, and seawater have been known since the times of ancient Rome and are still the object of research. During the last decade, there has been an increasing interest in self‐healing electronic materials, for applications in electronic skin (E‐skin) for health monitoring, wearable and stretchable sensors, actuators, transistors, energy harvesting, and storage devices. Self‐healing materials based on conducting polymers are particularly attractive due to their tunable high conductivity, good stability, intrinsic flexibility, excellent processability and biocompatibility. Here recent developments are reviewed in the field of self‐healing electronic materials based on conducting polymers, such as poly 3,4‐ethylenedioxythiophene (PEDOT), polypyrrole (PPy), and polyaniline (PANI). The different types of healing, the strategies adopted to optimize electrical and mechanical properties, and the various possible healing mechanisms are introduced. Finally, the main challenges and perspectives in the field are discussed.

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confidence: 99%

Recent Progress on Self‐Healable Conducting Polymers

Zhou

Sarkar

et al. 2022

Advanced Materials

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“…Taking advantage of the strong and dynamic boronic ester bonds as cross-linking sites, the resulting dynamic covalent 3OH-PBM polymers not only possess excellent self-healing ability under ambient conditions without any external stimulus (water, heat, light, etc.) but also achieve great mechanical strength and toughness simultaneously, which have never been reported in other relevant literatures (see Figure e, as well as Table S2 in the Supporting Information). ,,− ,,,− …”

Section: Resultsmentioning

confidence: 55%

A Tough and Self-Healing Polymer Enabled by Promoting Bond Exchange in Boronic Esters with Neighboring Hydroxyl Groups

Zhao

Wang

Zuo

et al. 2021

ACS Materials Lett.

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B–O bonds are effective for constructing self-healing polymers, because of their unique combination of high thermodynamic stability and kinetic tunability. However, it is still challenging to develop boron-containing polymers that show simultaneously high mechanical strength, good hydrolytic stability, and autonomous self-healing ability. Herein, we designed and synthesized a phenol compound with three hydroxyls, two of which form boronic ester with boronic acid while the other one can promote the dynamic exchange of B–O bonds. Taking advantage of the new boronic esters as the cross-linking sites, a series of strong and tough elastomers with outstanding self-healing capacities at room temperature were successfully fabricated. The new design concept provides a novel type of dynamic covalent boronic esters as the platform for synthesizing durable and functional self-healing materials. Moreover, phenol compounds with three hydroxyl groups are abundant in the natural product, tannic acid (TA), which can also form dynamic boronic esters with boronic acid and be used to derive polymers with excellent recyclability. Therefore, this new system might facilitate the commercialization of boron-based dynamic covalent polymers as viable alternatives to contemporary commodity thermosets.

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“…The high chemoselectivity of boronic acids towards diols makes them attractive for a variety of structures, such as macrocycles and cages. [12,23,[57][58][59][60][61][62] In this work, we demonstrate a match between boronates and the nitroalkanol functionalities generated through the nitroaldol reaction. The two processes could operate simultaneously under the same conditions, where the boronic ester formation and the nitroaldol reaction complemented each other.…”

Section: Introductionmentioning

confidence: 74%

Interdependent Dynamic Nitroaldol and Boronic Ester Reactions for Complex Dynamers of Different Topologies

Karalius

Ayinla

et al. 2021

Preprint

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Complex dynamic systems displaying interdependency between nitroaldol and boronic ester reactions have been demonstrated. Nitroalkane-1,3-diols, generated by the nitroaldol reaction, were susceptible to ester formation with different boronic acids in aprotic solvents, whereas hydrolysis of the esters occurred in the presence of water. The boronic ester formation led to significant stabilization of the nitroaldol adducts under basic conditions. The use of bifunctional building blocks was furthermore established, allowing for main chain nitroaldol-boronate dynamers as well as complex network dynamers with distinct topologies. The shape and rigidity of the resulting dynamers showed an apparent dependency on the configuration of the boronic acids.

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Recent progress in self-healing polymers and hydrogels based on reversible dynamic B–O bonds: boronic/boronate esters, borax, and benzoxaborole

Abstract: Intrinsic self-healing polymeric materials are substances that relieve external stress and restore their original mechanical properties after extreme damage via dynamic covalent bonding in the polymeric structure or the reversible...

Cited by 224 publications

References 134 publications

Recent Progress on Self‐Healable Conducting Polymers

Recent Progress on Self‐Healable Conducting Polymers

A Tough and Self-Healing Polymer Enabled by Promoting Bond Exchange in Boronic Esters with Neighboring Hydroxyl Groups

Interdependent Dynamic Nitroaldol and Boronic Ester Reactions for Complex Dynamers of Different Topologies

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