Abstract
This chapter summarizes the recent progress of the chemistry of triazole-based polymer gels from 2000 to present. Based on the gelation mechanism, the gels are classified into reversible physical and irreversible chemical gels. The design principles of these gel systems were examined, and the various driving forces for gelation, such as hydrogen bonding, π–π stacking interaction, hydrophobic effect, covalent linkage, and metal coordination, were described. Structural factors that affect the swelling ability of such gels and their applications in controlled drug release were revealed. The advantages and drawbacks of using CuAAC chemistry to create such gelating systems, as compared to other conventional synthetic methodologies, were also discussed.
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Finley KT (1980) Triazoles: 1,2,3. In: Montgomery JA (ed) The chemistry of heterocyclic compounds, vol 39. Wiley, New York
Tornøe CW, Christensen C, Meldal M (2002) Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkenes to azides. J Org Chem 67:3057–3064
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed 41:2596–2599
Binder WH, Kluger C (2006) Azide/alkyne-“click” reactions: applications in material science and organic synthesis. Curr Org Chem 10:1791–1815
Lutz JF (2007) 1,3-Dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science. Angew Chem Int Ed 46:1018–1025
Voit B (2007) The potential of cycloaddition reactions in the synthesis of dendritic polymers. New J Chem 31:1139–1151
Nandivada H, Jiang X, Lahann J (2007) Click chemistry: versatility and control in the hands of materials scientists. Adv Mater 19:2197–2208
Golas PL, Matyjaszewski K (2007) Click chemistry and ATRP: a beneficial union for the preparation of functional materials. QSAR Comb Sci 26:1116–1134
Fournier D, Hoogenboom R, Schubert US (2007) Clicking polymers: a straightforward approach to novel macromolecular architectures. Chem Soc Rev 36:1369–1380
Binder WH, Sachsenhofer R (2007) ‘Click’ chemistry in polymer and materials science. Macromol Rapid Commun 28:15–54
Binder WH, Sachsenhofer R (2008) ‘Click’ chemistry in polymer and material science: an update. Macromol Rapid Commun 29:952–981
Lundberg P, Hawker CJ, Hult A, Malkoch M (2008) Click assisted one-pot multi-step reactions in polymer science: accelerated synthetic protocols. Macromol Rapid Commun 29:998–1015
Meldal M (2008) Polymer “clicking” by CuAAC reactions. Macromol Rapid Commun 29:1016–1051
Johnson JA, Finn MG, Koberstein JT, Turro NJ (2008) Construction of linear polymers, dendrimers, networks, and other polymeric architectures by copper-catalyzed azide-alkyne cycloaddition “click” chemistry. Macromol Rapid Commun 29:1052–1072
Carlmark A, Hawker C, Hult A, Malkoch M (2009) New methodologies in the construction of dendritic materials. Chem Soc Rev 38:352–362
Iha RK, Wooley KL, Nyström AM, Burke DJ, Kade MJ, Hawker CJ (2009) Applications of orthogonal “click” chemistries in the synthesis of functional soft materials. Chem Rev 109:5620–5686
Billiet L, Fournier D, Du Prez F (2009) Step-growth polymerization and ‘click’ chemistry: the oldest polymers rejuvenated. Polymer 50:3877–3886
Golas PL, Matyjaszewski K (2010) Marrying click chemistry with polymerization: expanding the scope of polymeric materials. Chem Soc Rev 39:1338–1354
Dondoni A (2007) Triazoles: the keystone in glycosylated molecular architectures constructed by a click reaction. Chem Asian J 2:700–708
Angell YL, Burgess K (2007) Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions. Chem Soc Rev 36:1674–1689
Pieters RJ, Rijkers DTS, Liskamp RMJ (2007) Application of the 1,3-dipolar cycloaddition reaction in chemical biology: approaches toward multivalent carbohydrates and peptides and peptide-based polymers. QSAR Comb Sci 26:1181–1190
Dirks AJ, Cornelissen JJLM, van Delft FL, van Hest JCM, Nolte RMJ, Rowan AE, Rutjes FPJT (2007) From (bio)molecules to biohybrid materials with the click chemistry approach. QSAR Comb Sci 26:1200–1210
Le Droumaguet B, Velonia K (2008) Click chemistry: a powerful tool to create polymer-based macromolecular chimeras. Macromol Rapid Commun 29:1073–1089
Gramlich PME, Wirges CT, Manetto A, Carell T (2008) Postsynthetic DNA modification through the copper-catalyzed azide-alkyne cycloaddition reaction. Angew Chem Int Ed 47:8350–8358
Santoyo-Gonzalez F, Hernandez-Mateo F (2009) Silica-based clicked hybrid glyco materials. Chem Soc Rev 38:3449–3462
Amblard F, Cho JH, Schinazi RF (2009) Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide and oligonucleotide chemistry. Chem Rev 109:4207–4220
van Dijk M, Rijkers DTS, Liskamp RMJ, van Nostrum CF, Hennink WE (2009) Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies. Bioconjugate Chem 20:2001–2016
Chow HF, Lau KN, Ke Z, Liang Y, Lo CM (2010) Conformational and supramolecular properties of main chain and cyclic click oligotriazoles and polytriazoles. Chem Commun 46:3437–3453
Terech P, Weiss RG (1997) Low molecular mass gelators of organic liquids and the properties of their gels. Chem Rev 97:3133–3160
van Esch JH, Feringa BL (2000) New functional materials based on self-assembling organogels: from serendipity towards design. Angew Chem Int Ed 39:2263–2266
Estroff LA, Hamilton AD (2004) Water gelation by small organic molecules. Chem Rev 104:1201–1217
Fages F (ed) (2005) Low molecular mass gelators: design, self-assembly, function. In: Topics in current chemistry, vol 256. Springer, Berlin
Sangeetha NM, Maitra U (2005) Supramolecular gels: Functions and uses. Chem Soc Rev 34:821–836
de Loos M, Feringa BL, van Esch JH (2005) Design and application of self-assembled low molecular weight hydrogels. Eur J Org Chem 3615–3631
Weiss RG, Terech P (eds) (2006) Molecular gels. Materials with self-assembled fibrillar networks. Springer, Dordrecht
Dastidar P (2008) Suparmolecular gelling agents: can they be designed? Chem Soc Rev 37:2699–2715
Suzuki M, Hanabusa K (2010) Polymer organogelators that make supramolecular organogels through physical cross-linking and self-assembly. Chem Soc Rev 39:455–463
Díaz DD, Rajagopal K, Strable E, Schneider J, Finn MG (2006) “Click” chemistry in a supramolecular environment: stabilization of organogels by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition. J Am Chem Soc 128:6056–6057
Díaz DD, Tellado JJM, Velázquez DG, Ravelo AG (2008) Polymer thermoreversible gels from organogelators enabled by ‘click’ chemistry. Tetrahedron Lett 49:1340–1343
Díaz DD, Cid JJ, Vázquez P, Torres T (2008) Strength enhancement of nanostructured organogels through inclusion of phthalocyanine-containing complementary organogelator structures and in situ cross-linking by click chemistry. Chem Eur J 14:9261–9273
Binder WH, Petraru L, Roth T, Groh PW, Pálfi V, Keki S, Ivan B (2007) Magnetic and temperature-sensitive release gels from supramolecular polymers. Adv Funct Mater 17:1317–1326
Lau KN, Chow HF, Chan MC, Wong KW (2008) Dendronized polymer organogels from click chemistry: a remarkable gelation property owing to synergistic function-group binding and dendritic size effects. Angew Chem Int Ed 47:6912–6916
Chow HF, Lau KN, Chan MC (2011) Click dendronized poly(amide–triazole)s: effect of dendron size and polymer backbone symmetry on self assembling and gelation properties. Chem Eur J. 17:8395–8403
Schlüter AD (2005) A covalent chemistry approach to giant macromolecules with cylindrical shape and an engineerable interior and surface. Top Curr Chem 245:151–191
Chen Y, Pang XH, Dong CM (2010) Dual stimuli-responsive supramolecular polypeptide-based hydrogel and reverse micellar hydrogel mediated by host-guest chemistry. Adv Funct Mater 20:579–586
Reinicke S, Schmalz H (2011) Combination of living anionic polymerization and ATRP via “click” chemistry as a versatile route to multiple responsive triblock terpolymers and corresponding hydrogels. Colloid Polym Sci 289:497–512
Ossipov DA, Hilborn J (2006) Poly(vinyl alcohol)-based hydrogels formed by “click chemistry”. Macromolecules 39:1709–1718
Malkoch M, Vestberg R, Gupta N, Mespouille L, Dubois P, Mason AF, Hedrick JL, Liao Q, Frank CW, Kingsbury K, Hawker CJ (2006) Synthesis of well-defined hydrogel networks using click chemistry. Chem Commun 2774–2776
Xu XD, Chen CS, Wang ZC, Wang GR, Cheng SX, Zhang XZ, Zhuo RX (2008) “Click” chemistry for in situ formation of thermoresponsive p(NIPAAm-co-HEMA)-based hydrogels. J Polym Sci Polym Chem 46:5263–5277
Xu XD, Chen CS, Lu B, Wang ZC, Cheng SX, Zhang XZ, Zhuo RX (2009) Modular synthesis of thermosensitive p(NIPAAm-co-HEMA)-β-CD based hydrogels via click chemistry. Macromol Rapid Commun 30:157–164
Clark M, Kiser P (2009) In situ crosslinked hydrogels formed using Cu(I)-free Huisgen cycloaddition reaction. Polym Int 58:1190–1195
Crescenzi V, Cornelio L, Di Meo C, Nardecchia S, Lamanna R (2007) Novel hydrogels via click chemistry: synthesis and potential biomedical applications. Biomacromolecules 8:1844–1850
Testa G, Di Meo C, Nardecchia S, Capitani D, Mannina L, Lamanna R, Barbetta A, Dentini M (2009) Influence of dialkyne structure on the properties of new click-gels based on hyaluronic acid. Int J Pharm 378:86–92
Polizzotti BD, Fairbanks BD, Anseth KS (2008) Three-dimensional biochemical patterning of click-based composite hydrogels via thiolene photopolymerization. Biomacromolecules 9:1084–1087
Hoyle CE, Bowman CN (2010) Thiol-ene click chemistry. Angew Chem Int Ed 49:1540–1573
DeForest CA, Sims EA, Anseth KS (2010) Peptide-functionalized click hydrogels with independently tunable mechanics and chemical functionality for 3D cell culture. Chem Mater 22:4783–4790
Baskin JM, Prescher JA, Laughlin ST, Agard NJ, Chang PV, Miller IA, Lo A, Codelli JA, Bertozzi CR (2007) Copper-free click chemistry for dynamic in vivo imaging. Proc Natl Acad Sci USA 104:16793–16797
Codelli JA, Baskin JM, Agard NJ, Bertozzi CR (2008) Second-generation difluorinated cyclooctynes for copper-free click chemistry. J Am Chem Soc 130:11486–11493
Altin H, Kosif I, Sanyal R (2010) Fabrication of “clickable” hydrogels via dendron–polymer conjugates. Macromolecules 43:3801–3808
De Geest BG, Van Camp W, Du Prez FE, De Smedt SC, Demeester J, Hennink WE (2008) Biodegradable microcapsules designed via ‘click’ chemistry. Chem Commun 190–192
Zednik J, Riva R, Lussis P, Jérôme C, Jérôme R, Lecomte P (2008) pH-Responsive biodegradable amphiphilic networks. Polymer 49:697–702
Liu SQ, Ee PLR, Ke CY, Hedrick JL, Yang YY (2009) Biodegradable poly(ethylene glycol)-peptide hydrogels with well-defined structure and properties for cell delivery. Biomaterials 30:1453–1461
Ruoslahti E, Pierschbacher MD (1987) New perspectives in cell adhesion: RGD and integrins. Science 238:491–497
van Dijk M, van Nostrum CF, Hennink WE, Rijkers DTS, Liskamp RMJ (2010) Synthesis and characterization of enzymatically biodegradable PEG and peptide-based hydrogels prepared by click chemistry. Biomacromolecules 11:1608–1614
Yang J, Jacobsen MT, Pan H, Kopeček J (2010) Synthesis and characterization of enzymatically degradable PEG-based peptide-containing hydrogels. Macromol Biosci 10:445–454
Antoni P, Hed Y, Nordberg A, Nyström D, von Holst H, Hult A, Malkoch M (2009) Bifunctional dendrimers: from robust synthesis and accelerated one-pot postfunctionalization strategy to potential applications. Angew Chem Int Ed 48:2126–2130
Xia Y, Verduzco R, Grubbs RH, Kornfield JA (2008) Well-defined liquid crystal gels from telechelic polymers. J Am Chem Soc 130:1735–1740
Meudtner RM, Hecht S (2008) Responsive backbones based on alternating triazole-pyridine/benzene copolymers: from helically folding polymers to metallosupramolecularly crosslinked gels. Macromol Rapid Commun 29:347–351
Meudtner RM, Ostermeier M, Goddard R, Limberg C, Hecht S (2007) Multifunctional “clickates” as versatile extended heteroaromatic building block: efficient synthesis via click chemistry, conformational preferences, and metal coordination. Chem Eur J 13:9834–9840
Johnson JA, Lewis DR, Díaz DD, Finn MG, Koberstein JT, Turro NJ (2006) Synthesis of degradable model networks via ATRP and click chemistry. J Am Chem Soc 128:6564–6565
Acknowledgment
We thank the Research Grants Council, HKSAR, for the financial support (Project Number: 400810).
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Chow, HF., Lo, CM., Chen, Y. (2012). Triazole-Based Polymer Gels. In: Košmrlj, J. (eds) Click Triazoles. Topics in Heterocyclic Chemistry, vol 28. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_66
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DOI: https://doi.org/10.1007/7081_2011_66
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