Click Chemistry: Mechanistic and Synthetic Perspectives

Ramapanicker, Ramesh; Chauhan, Pooja

doi:10.1002/9783527694174.ch1

Cited by 12 publications

(12 citation statements)

References 96 publications

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“…The reactivity of the alkene group decreases as the electron density of the double bond decreases. 69 Northrop and Coffey have modeled the kinetics of the radical-initiated thiol−ene reaction between a methyl mercaptan (H 3 C−SH) and a series of different alkenes. 67 As can be seen in Figure 3, the kinetics of the thiol−ene reaction is highly dependent on the reactivity of the chosen alkene, with norbornene proving to have the highest reactivity.…”

Section: Photopolymerization Mechanisms 21 Free-radical Chain Growth ...mentioning

confidence: 99%

“…The inherent ring strain of norbornene causes its double bond to be highly reactive for a thiyl radical attack as well as a radical intermediate for abstracting the thiol hydrogen to generate the thiyl radical. 45,69 As such, thiol−norbornene chemistry has been a popular choice in the literature for lightbased 3D printing. 52,70−77 2.2.5.…”

Section: Photopolymerization Mechanisms 21 Free-radical Chain Growth ...mentioning

confidence: 99%

“…Most click reactions occur either spontaneously or via catalysis, although few can be controlled with light. ,− One that has been exploited recently, although its mechanism has been known for some time, is the photoinduced thiol–ene reaction. ,,− For context, the thiol–ene reaction is historically differentiated from the Michael addition reaction based upon the reaction condition. Specifically, the thiol–ene reaction requires a free-radical initiator, whereas the thiol-Michael addition requires a chemical catalyst, although some consider the photoinduced mechanism to be a type of thiol-Michael addition pathway. , The orthogonal nature of the thiol–ene mechanism allows for the formation of homogeneous hydrogel networks of consistent properties.…”

Section: Photopolymerization Mechanismsmentioning

confidence: 99%

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Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications

et al. 2020

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Since the advent of additive manufacturing, known commonly as 3D printing, this technology has revolutionized the biofabrication landscape and driven numerous pivotal advancements in tissue engineering and regenerative medicine. Many 3D printing methods were developed in short course after Charles Hull first introduced the power of stereolithography to the world. However, materials development was not met with the same enthusiasm and remained the bottleneck in the field for some time. Only in the past decade has there been deliberate development to expand the materials toolbox for 3D printing applications to meet the true potential of 3D printing technologies. Herein, we review the development of biomaterials suited for light-based 3D printing modalities with an emphasis on bioprinting applications. We discuss the chemical mechanisms that govern photopolymerization and highlight the application of natural, synthetic, and composite biomaterials as 3D printed hydrogels. Because the quality of a 3D printed construct is highly dependent on both the material properties and processing technique, we included a final section on the theoretical and practical aspects behind light-based 3D printing as well as ways to employ that knowledge to troubleshoot and standardize the optimization of printing parameters.

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Section: Photopolymerization Mechanisms 21 Free-radical Chain Growth ...mentioning

confidence: 99%

Section: Photopolymerization Mechanisms 21 Free-radical Chain Growth ...mentioning

confidence: 99%

Section: Photopolymerization Mechanismsmentioning

confidence: 99%

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Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications

et al. 2020

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“…A controlled environment on the polymerization of the precursors combined with functionalization reactions can yield stable macromolecules. In addition, the incorporation of ‘click’ chemistry via cupper-catalyzed reactions allows targeting a specific molecule due to its stereo-selective mechanism [ 13 ]. It is noteworthy that, after etching one of the nano-template phases, functional groups embedded onto porous matrices are highly likely to preserve their chemical properties due to the existing covalent bond [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Triazole-Functionalized Mesoporous Materials Based on Poly(styrene-block-lactic acid): A Morphology Study of Thin Films

et al. 2022

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We report the synthesis of poly(styrene-block-lactic acid) (PS-b-PLA) copolymers with triazole rings as a junction between blocks. These materials were prepared via a ‘click’ strategy which involved the reaction between azide-terminated poly(styrene) (PS-N3) and acetylene-terminated poly(D,L-lactic acid) (PLA-Ac), accomplished by copper-catalyzed azide-alkyne cycloaddition reaction. This synthetic approach has demonstrated to be effective to obtain specific copolymer structures with targeted self-assembly properties. We observed the self-assembly behavior of the PS-b-PLA thin films as induced by solvent vapor annealing (SVA), thermal annealing (TA), and hydrolysis of the as-spun substrates and monitored their morphological changes by means of different microscopic techniques. Self-assembly via SVA and TA proved to be strongly dependent on the pretreatment of the substrates. Microphase segregation of the untreated films yielded a pore size of 125 nm after a 45-min SVA. After selectively removing the PLA microdomains, the as-spun substrates exhibited the formation of pores on the surface, which can be a good alternative to form an ordered pattern of triazole functionalized porous PS at the mesoscale. Finally, as revealed by scanning electron microscopy–energy dispersive X-ray spectroscopy, the obtained triazole-functionalized PS-porous film exhibited some affinity to copper (Cu) in solution. These materials are suitable candidates to further study its metal-caption properties.

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“… 1 A prominent application of these systems is in the synthesis of nitrogen-containing heterocycles, such as the prototypical click reaction between substituted azides and alkynes to form triazoles. 2 Less nitrogen-rich heterocycles can also be assembled with other 1,3-dipoles, such as pyrroles (from münchnones), pyrazoles (from sydnones), and related systems. 3,4 This breadth is driven in part by the availability of stabilized nitrogen-based 1,3-dipoles of use in cycloaddition, many of which were developed in the pioneering work of Huisgen.…”

Section: Introductionmentioning

confidence: 99%

Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans

2021

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Click Chemistry: Mechanistic and Synthetic Perspectives

Cited by 12 publications

References 96 publications

Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications

Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications

Triazole-Functionalized Mesoporous Materials Based on Poly(styrene-block-lactic acid): A Morphology Study of Thin Films

Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans

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