Adv Polym Sci (2020) 285: 243–294
https://doi.org/10.1007/12_2019_59
© Springer Nature Switzerland AG 2020
Published online: 24 April 2020
Self-Healing Hydrogels Based on Reversible
Covalent Linkages: A Survey of Dynamic
Chemical Bonds in Network Formation
Ruveyda Kilic and Amitav Sanyal
Contents
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 244
2 Imine Bond Formation-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 245
2.1 Cross-Linking of Natural Polymers Using Imine-Based Linkages . . . . . . . . . . . . . . . . . . 246
2.2 Cross-Linking of Synthetic Polymers Through Imine Linkages . . . . . . . . . . . . . . . . . . . . . 254
3 Acylhydrazone Bond Formation-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 257
3.1 Cross-Linking of Synthetic Polymers Through Acylhydrazone Linkages . . . . . . . . . . 257
3.2 Cross-Linking of Natural Polymers Through Acylhydrazone Linkages . . . . . . .. . . . . . 263
4 Boronic Ester Bond Formation Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
4.1 Cross-Linking of Synthetic Polymers Through Boronic Ester Linkages . . . . . . . . . . . . 265
4.2 Cross-Linking of Natural Polymers Through Boronic Ester Linkages . . . . . . . . . . . . . . 271
5 Diels-Alder Cycloaddition-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 273
6 Disulfide Bond Formation-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 274
7 Photo-Responsive Linkage-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 278
8 Dual-Responsive Self-Healing Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 282
9 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 289
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 290
Abstract Over the past decade, the design of hydrogels has transformed from
fabrication of static cross-linked materials to dynamic systems, which upon damage
can potentially self-heal to their original state, either autonomously or through the
help of external stimuli. This chapter highlights, through examples, the synthesis and
R. Kilic
Department of Chemistry, Bogazici University, Istanbul, Turkey
A. Sanyal (*)
Department of Chemistry, Bogazici University, Istanbul, Turkey
Center for Life Sciences and Technologies, Bogazici University, Istanbul, Turkey
e-mail: amitav.sanyal@boun.edu.tr
https://doi.org/10.1007/12_2019_59
© Springer Nature Switzerland AG 2020
Published online: 24 April 2020
Self-Healing Hydrogels Based on Reversible
Covalent Linkages: A Survey of Dynamic
Chemical Bonds in Network Formation
Ruveyda Kilic and Amitav Sanyal
Contents
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 244
2 Imine Bond Formation-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 245
2.1 Cross-Linking of Natural Polymers Using Imine-Based Linkages . . . . . . . . . . . . . . . . . . 246
2.2 Cross-Linking of Synthetic Polymers Through Imine Linkages . . . . . . . . . . . . . . . . . . . . . 254
3 Acylhydrazone Bond Formation-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 257
3.1 Cross-Linking of Synthetic Polymers Through Acylhydrazone Linkages . . . . . . . . . . 257
3.2 Cross-Linking of Natural Polymers Through Acylhydrazone Linkages . . . . . . .. . . . . . 263
4 Boronic Ester Bond Formation Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
4.1 Cross-Linking of Synthetic Polymers Through Boronic Ester Linkages . . . . . . . . . . . . 265
4.2 Cross-Linking of Natural Polymers Through Boronic Ester Linkages . . . . . . . . . . . . . . 271
5 Diels-Alder Cycloaddition-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 273
6 Disulfide Bond Formation-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 274
7 Photo-Responsive Linkage-Based Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 278
8 Dual-Responsive Self-Healing Hydrogels . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 282
9 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 289
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 290
Abstract Over the past decade, the design of hydrogels has transformed from
fabrication of static cross-linked materials to dynamic systems, which upon damage
can potentially self-heal to their original state, either autonomously or through the
help of external stimuli. This chapter highlights, through examples, the synthesis and
R. Kilic
Department of Chemistry, Bogazici University, Istanbul, Turkey
A. Sanyal (*)
Department of Chemistry, Bogazici University, Istanbul, Turkey
Center for Life Sciences and Technologies, Bogazici University, Istanbul, Turkey
e-mail: amitav.sanyal@boun.edu.tr