Abstract
Various dynamic covalent bonds have been studied in the area of supramolecular gels, such as imine/acylhydrazone formation, boronic ester formation, disulphide formation and anthracene dimerization. Two catalogues of dynamic covalent gels are discussed in this chapter, namely gelation by discrete molecules and gelation by dynamic covalent polymers. Discrete gelators include imine/acylhydrazone gels, borate gels, anthracene-based gels and gels based on dynamic covalent cycles and cages. In the section of dynamic covalent polymer gels, imine gels and calix[4]arene-derived acylhydrazone gels are discussed in detail.
Jianyong Zhang, Haobin Fang and Xiying Feng contributed together to this chapter.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Lehn J-M (2007) From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry. Chem Soc Rev 36:151–160
Luo W, Zhu Y, Zhang J, He J, Chi Z, Miller PW, Chen L, Su C-Y (2014) A dynamic covalent imine gel as a luminescent sensor. Chem Commun 50:11942–11945
Foster JS, Żurek JM, Almeida NMS, Hendriksen WE, le Sage VAA, Lakshminarayanan V, Thompson AL, Banerjee R, Eelkema R, Mulvana H, Paterson MJ, van Esch JH, Lloyd GO (2015) Gelation landscape engineering using a multi-reaction supramolecular hydrogelator system. J Am Chem Soc 137:14236–14239
Boekhoven J, Poolman JM, Maity C, Li F, van der Mee L, Minkenberg CB, Mendes E, van EschJan H, Eelkema R (2013) Catalytic control over supramolecular gel formation. Nat Chem 5:433–437
Li J, Carnall JMA, Stuart MCA, Otto S (2011) Hydrogel formation upon photoinduced covalent capture of macrocycle stacks from dynamic combinatorial libraries. Angew Chem Int Ed 50:8384–8386
Belowicha ME, Stoddart JF (2012) Dynamic imine chemistry. Chem Soc Rev 41:2003–2024
Zhang JY, Zeng LH, Feng J (2017) Dynamic covalent gels assembled from small molecules: from discrete gelators to dynamic covalent polymers. Chin Chem Lett 28:168–183
Wang Y-J, Xing P-Y, Li S-Y, Ma M-F, Yang M-M, Zhang Y-M, Wang B, Hao A-Y (2016) Facile stimuli-responsive transformation of vesicle to nanofiber to supramolecular gel via ω-amino acid-based dynamic covalent chemistry. Langmuir 32:10705–10711
Yu X-D, Xie D-Y, Li Y-J, Geng L-J, Ren J-J, Wang T, Pang X-L (2017) Photochromic property of naphthalimide derivative: selective and visual F− recognition by NSS isomers both in solution and in a self-assembly gel. Sens Actuators B 251:828–835
Rajamalli P, Prasad E (2011) Low molecular weight fluorescent organogel for fluoride ion detection. Org Lett 13:3714–3717
Rajamalli P, Prasad E (2012) Non-amphiphilic pyrene cored poly(aryl ether) dendron based gels: tunable morphology, unusual solvent effects on the emission and fluoride ion detection by the self-assembled superstructures. Soft Matter 8:8896–8903
Lakshmi NV, Mandal D, Ghosh S, Prasad E (2014) Multi-stimuli-responsive organometallic gels based on ferrocene-linked poly(aryl ether) dendrons: reversible redox switching and Pb2+-Ion Sensing. Chem Eur J 20:9002–9011
Lv K, Zhang L, Liu M-H (2014) Self-assembly of triangular amphiphiles into diverse nano/ microstructures and release behavior of the hollow sphere. Langmuir 30:9295–9302
Poolman JM, Maity C, Boekhoven J, van der Mee L, le Sage VAA, Groenewold GJM, van Kasteren SI, Versluis F, van Esch JH, Eelkema R (2016) A toolbox for controlling the properties and functionalisation of hydrazone-based supramolecular hydrogels. J Mater Chem B 4:852–858
Sreenivasachary N, Lehn J-M (2005) Gelation-driven component selection in the generation of constitutional dynamic hydrogels based on guanine-quartet formation. Proc Natl Acad Sci U S A 102:5938–5943
Bunzen H, Nonappa Kalenius E, Hietala S, Kolehmainen E (2013) Subcomponent self-assembly: a quick way to new metallogels. Chem Eur J 19:12978–12981
Zang L-B, Shang H-X, Wei D-Y, Jiang S-M (2013) A multi-stimuli-responsive organogel based on salicylidene Schiff base. Sens Actuators B 185:389–397
Sun J-G, Liu Y-C, Jin L-Y, Chen T, Yin B-Z (2016) Coordination-induced gelation of an L-glutamic acid Schiff base derivative: the anion effect and cyanide-specific selectivity. Chem Commun 52:768–771
Dixit MK, Pandey VK, Dubey M (2016) Alkali base triggered intramolecular charge transfer metallogels based on symmetrical A–π–d-chiral-d–π–A type ligands. Soft Matter 12:3622–3630
Sarmah K, Pandit G, Das AB, Sarma B, Pratihar S (2017) Steric environment triggered self-healing CuII/HgII bimetallic gel with old CuII-Schiff Base complex as a new metalloligand. Cryst Growth Des 17:368–380
Rajamalli P, Malakar P, Atta S, Prasad E (2014) Metal induced gelation from pyridine cored poly (aryl ether) dendrons with in situ synthesis and stabilization of hybrid hydrogel composites. Chem Commun 50:11023–11025
Lin Q, Sun B, Yang Q-P, Fu Y-P, Zhu X, Wei T-B, Zhang Y-M (2014) Double metal ions competitively control the guest-sensing process: a facile approach to stimuli-responsive supramolecular gels. Chem Eur J 20:11457–11462
Lin Q, Yang Q-P, Sun B, Fu Y-P, Zhu X, Wei T-B, Zhang Y-M (2014) Rewritable security display material and Cl− sensor: based on a bimetal competitive coordination controlled supramolecular gel. Mater Lett 137:444–446
Lin Q, Sun B, Yang Q-P, Fu Y-P, Zhu X, Zhang Y-M, Wei T-B (2014) A novel strategy for the design of smart supramolecular gels: controlling stimuli-response properties through competitive coordination of two different metal ions. Chem Commun 50:10669–10671
Lin Q, Yang Q-P, Sun B, Fu Y-P, Zhu X, Wei T-B, Zhang Y-M (2014) Competitive coordination control of the AIE and micro states of supramolecular gel: an efficient approach for reversible dual-channel stimuli-response materials. Soft Matter 10:8427–8432
Lin Q, Lu T-T, Zhu X, Sun B, Yang Q-P, Wei T-B, Zhang Y-M (2015) A novel supramolecular metallogel-based high-resolution anion sensor array. Chem Commun 51:1635–1638
Lin Q, Lu T-T, Zhu X, Wei T-B, Li H, Zhang Y-M (2016) Rationally introduce multi-competitive binding interactions in supramolecular gels: a simple and efficient approach to develop multi-analyte sensor array. Chem Sci 7:5341–5346
Peters GM, Skala LP, Plank TN, Hyman BJ, Reddy GNM, Marsh A, Brown SP, Davis JT (2014) A G4 K+ hydrogel stabilized by an anion. J Am Chem Soc 136:12596–12599
Peters GM, Skala LP, Plank TN, Oh H, Reddy GNM, Marsh A, Brown SP, Raghavan SR, Davis JT (2015) G4-quartet M+ borate hydrogels. J Am Chem Soc 137:5819–5827
Plank TN, Davis JT (2016) A G4 K+ hydrogel that self-destructs. Chem Commun 52:5037–5040
Venkatesh V, Mishra NK, Romero-Canelon I, Vernooij RR, Shi H-Y, Coverdale JPC, Habtemariam A, Verma S, Sadler PJ (2017) Supramolecular photoactivatable anticancer hydrogels. J Am Chem Soc 139:5656–5659
Xu J-F, Chen Y-Z, Wu L-Z, Tung C-H, Yang Q-Z (2013) Dynamic covalent bond based on reversible photo [4+4] cycloaddition of anthracene for construction of double-dynamic polymers. Org Lett 15:6148–6151
Jin Y-H, Wang Q, Taynton P, Zhang W (2014) Dynamic covalent chemistry approaches toward macrocycles, molecular cages, and polymers. Acc Chem Res 47:1575–1586
Jin Y, Jin A, McCaffrey R, Long H, Zhang W (2012) Design strategies for shape-persistent covalent organic polyhedrons (COPs) through imine condensation/metathesis. J Org Chem 77:7392–7400
Hasell T, Little MA, Chong S-Y, Schmidtmann M, Briggs EM, Santolini V, Jelfs KE, Cooper AI (2017) Chirality as a tool for function in porous organic cages. Nanoscale 9:6783–6790
Jin Y, Zhu Y, Zhang W (2013) Development of organic porous materials through schiff-base chemistry. Cryst Eng Comm 15:1484–1499
Hasell T, Cooper AI (2016) Porous organic cages: soluble, modular and molecular pores. Nat Rev Mater 1:16053
Šolomek T, Powers-Riggs NE, Wu Y-L, Young RM, Krzyaniak MD, Horwitz NE, Wasielewski MR (2017) Electron hopping and charge separation within a naphthalene-1,4:5,8-bis(dicarboximide) chiral covalent organic cage. J Am Chem Soc 139:3348–3351
Akine S, Miyashita M, Nabeshima T (2017) A metallo-molecular cage that can close the apertures with coordination bonds. J Am Chem Soc 139:4631–4634
Chen H-Y, Gou M, Wang J-B (2017) De novo endo-functionalized organic cages as cooperative multi-hydrogen-bond-donating catalysts. Chem Commun 53:3524–3526
Hasell T, Miklitz M, Stephenson A, Little MA, Chong SY, Clowes R, Chen L-J, Holden D, Tribello GA, Jelfs KE, Cooper AI (2016) Porous organic cages for sulfur hexafluoride separation. J Am Chem Soc 138:1653–1659
Zhang G, Presly O, White F, Oppel IM, Mastalerz M (2014) A permanent mesoporous organic cage with an exceptionally high surface area. Angew Chem Int Ed 53:1516–1520
Ide T, Takeuchi D, Osakada K (2012) Columnar self-assembly of rhomboid macrocyclic molecules via step-like intermolecular interaction. Crystal Formation Gelation Chem Commun 48:278–280
Xue M, Lu Y-C, Sun O-O, Liu K-Q, Liu Z, Sun P (2015) Ag (I)-coordinated supramolecular metallogels based on schiff base ligands: structural characterization and reversible thixotropic property. Cryst Growth Des 15:5360–5367
Ito S, Takata H, Ono K, Iwasawa N (2013) Release and recovery of guest molecules during the reversible borate gel formation of guest-included macrocyclic boronic esters. Angew Chem Int Ed 52:11045–11048
Li J-W, Carnall JMA, Stuart MCA, Otto S (2011) Hydrogel formation upon photoinduced covalent capture of macrocycle stacks from dynamic combinatorial libraries. Angew Chem 123:8534–8536
Zhang J-Y, Liu L-P, Liu H-L, Lin M-J, Li S-Y, Ouyang G-F, Chen L-P, Su C-Y (2015) Highly porous aerogels based on imine chemistry: syntheses and sorption properties. J Mater Chem A 3:10990–10998
Zeng L-H, Liao P-S, Liu H-L, Liu L-P, Liang Z-W, Zhang J-Y, Chen L-P, Su C-Y (2016) Impregnation of metal ions into porphyrin-based imine gels to modulate guest uptake and to assemble a catalytic microfluidic reactor. J Mater Chem A 4:8328–8336
Liu H-L, Feng J, Zhang J-Y, Miller PW, Chen L-P, Su C-Y (2015) A catalytic chiral gel microfluidic reactor assembled via dynamic covalent chemistry. Chem Sci 6:2292–2296
Lee J-H, Park J, Park J-W, Ahn H-J, Jaworski J, Jung J-H (2015) Supramolecular gels with high strength by tuning of calix[4]arene-derived networks. Nat Commun 6:6650–6658
Lee J-H, Jung S-H, Lee S-S, Kwon K-Y, Sakurai K, Jaworski J, Jung J-H (2017) Ultraviolet patterned calixarene-derived supramolecular gels and films with spatially resolved mechanical and fluorescent properties. ACS Nano 11:4155–4164
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2018 Springer Nature Singapore Pte Ltd.
About this chapter
Cite this chapter
Zhang, J., Hu, Y., Li, Y. (2018). Dynamic Covalent Gels. In: Gel Chemistry. Lecture Notes in Chemistry, vol 96. Springer, Singapore. https://doi.org/10.1007/978-981-10-6881-2_4
Download citation
DOI: https://doi.org/10.1007/978-981-10-6881-2_4
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-10-6880-5
Online ISBN: 978-981-10-6881-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)