Synthesis of well-defined hydrogel networks using Click chemistry

Malkoch, Michael; Vestberg, Robert; Gupta, Nalini; Mespouille, Laetitia; Dubois, Philippe; Mason, Andrew F.; Hedrick, James L.; Liao, Qi; Frank, Curtis W.; Kingsbury, Kevin B.; Hawker, Craig J.

doi:10.1039/b603438a

Cited by 508 publications

(489 citation statements)

References 27 publications

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“…The resulting hydrogel showed a water uptake that reached 300 % of its initial weight, which is in the same order of magnitude of state of the art related hydrogel materials ( Figure S11). [13] A desirable side effect of the preparation described herein is that the scaffolds formed inherently possess pendant thiol groups on their internal structure (Scheme 1), which are clearly discernible in the Raman spectra (e.g., Figure 3 b). This functionality can further be utilized through post-polymerization modification steps, [3] allowing versatile interface decoration of the generic scaffolds by thiol-ene chemistry even in the absence of initiator.…”

Section: Filipa Alves and Ivo Nischang* [A]mentioning

confidence: 99%

Tailor‐Made Hybrid Organic–Inorganic Porous Materials Based on Polyhedral Oligomeric Silsesquioxanes (POSS) by the Step‐Growth Mechanism of Thiol‐Ene “Click” Chemistry

Alves

Nischang

2013

Chemistry A European J

100

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Section: Filipa Alves and Ivo Nischang* [A]mentioning

confidence: 99%

Tailor‐Made Hybrid Organic–Inorganic Porous Materials Based on Polyhedral Oligomeric Silsesquioxanes (POSS) by the Step‐Growth Mechanism of Thiol‐Ene “Click” Chemistry

Alves

Nischang

2013

Chemistry A European J

100

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“…The Diels-Alder cycloaddition reac-tion [24][25][26] and thiol-ene chemistry [27,28] have recently been introduced as alternative click routes for providing new materials. Click reactions have been widely used for the synthesis of polymers with different compositions and topologies, ranging from linear (telechelic [29], macromonomer [30,31], macrophotoinitiator [32,33] and block co-polymer [34][35][36]) to nonlinear macromolecular structures (graft [37][38][39], star [40,41], miktoarm star [42,43], H-type [44], dendrimer [45][46][47], dendronized linear polymers [48,49], macrocyclic polymers [50,51], self-curable polymers [52][53][54], network systems [55,56] and polymeric nanoparticles [14,57]). Recently, the development and application of click chemistry in polymer and material science has been extensively reviewed [58][59][60][61][62][63].…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Cross-linking of Polymers Using Difunctional Acetylenes via Click Chemistry

Cengiz

Aydoğan

Ates

et al. 2011

Designed Monomers and Polymers

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An efficient approach was described for the intramolecular cross-linking of azide-functionalized poly(styrene-co-chloromethyl styrene) co-polymers (PS-N 3 ) via click chemistry at room temperature. Reaction of PS-N 3 with the appropriate diacetylene functional compounds such as 1,4-diethynylbenzene (DEB) and 1,10-dipropargyloxy decane (DPD) in ultra-dilute solutions led to unimolecular particle-like structures. The resulting polymers were characterized in detail by 1 H-NMR, FT-IR, GPC and DSC measurements.

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“…48,49 In that approach, copper (I)-catalyzed 1,2,3-triazoles formed from azides and terminal acetylene were used for a specific click reaction (Figure 10). 50 The unreacted azide and/or acetylene groups allow the incorporation of various additives and functional groups in the hydrogel network without affecting network formation, and the gelation can be performed under mild conditions at room temperature.…”

Section: Tetra-peg Gelsmentioning

confidence: 99%

Recent advances in hydrogels in terms of fast stimuli responsiveness and superior mechanical performance

Imran

Seki

Takeoka

2010

Polym J

139

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This review addresses the potential development of polymer hydrogels in terms of fast stimuli responsiveness and superior mechanical properties. The slow response and mechanical weakness of stimuli-sensitive hydrogels have been considered as the main barriers for their further development and practical application. It has been a dream of scientists to have fast stimuliresponsive hydrogels with superior mechanical performance. In this review, the principal reasons behind the poor stimulus sensitivity and mechanical strength of polymer gels are highlighted, and we present some pioneering physical and chemical efforts aimed at fabricating hydrogels with high stimuli sensitivities and/or superior mechanical properties. Polymer Journal ( Keywords: butterfly pattern; fast stimuli sensitivity; hydrogel; LCST; mechanical property INTRODUCTION Polymer hydrogels (hereafter called 'hydrogels') are three-dimensional polymer networks in which the voids are filled with water. These hydrogels are widely used in a variety of industrial and consumer products such as oil dewatering systems, mechanical absorbers, diapers and contact lenses. One of the most remarkable areas of research on hydrogels in the past few decades has been their stimulus sensitivity. Hydrogels composed of stimuli-responsive polymers reversibly alter their shape and volume in response to small variations in the environment, such as pH, temperature, light and electric and magnetic fields, thereby changing their physico-chemical characteristics. 1 Among all of the available environmentally responsive hydrogels, temperature-responsive hydrogels have attracted the most attention because of the facile tuning of their properties. In particular, poly(Nisopropylacrylamide) (poly(NIPA)) hydrogels have been widely investigated as thermosensitive hydrogels. Poly(NIPA) has a low critical solution temperature (LCST) at around 32 1C in water. The flexible coil of poly(NIPA) (soluble) converts into a compact globular state (insoluble) at the LCST, and this conformational change is reversible. 2 Thus, hydrogels composed of poly(NIPA) undergo a reversible volume change at a similar transition temperature in water. Poly(NIPA) hydrogels have potential applications in drug delivery systems, therapeutic agents, diagnostic devices, biomaterials, cell cultivation, biocatalysts, sensors, microfluidic devices, actuators, optical devices and size-selective separation among others. [3][4][5] A recent subject that has attracted much attention in the field of gel science is the fabrication of hydrogels with the rapid stimuli responsiveness and superior mechanical properties required for many applications of stimuli-responsive hydrogels. The creation of durable

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Synthesis of well-defined hydrogel networks using Click chemistry

Cited by 508 publications

References 27 publications

Tailor‐Made Hybrid Organic–Inorganic Porous Materials Based on Polyhedral Oligomeric Silsesquioxanes (POSS) by the Step‐Growth Mechanism of Thiol‐Ene “Click” Chemistry

Tailor‐Made Hybrid Organic–Inorganic Porous Materials Based on Polyhedral Oligomeric Silsesquioxanes (POSS) by the Step‐Growth Mechanism of Thiol‐Ene “Click” Chemistry

Intramolecular Cross-linking of Polymers Using Difunctional Acetylenes via Click Chemistry

Recent advances in hydrogels in terms of fast stimuli responsiveness and superior mechanical performance

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