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      Thiol-Ene Click Chemistry

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      Angewandte Chemie International Edition
      Wiley

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          Abstract

          Following Sharpless' visionary characterization of several idealized reactions as click reactions, the materials science and synthetic chemistry communities have pursued numerous routes toward the identification and implementation of these click reactions. Herein, we review the radical-mediated thiol-ene reaction as one such click reaction. This reaction has all the desirable features of a click reaction, being highly efficient, simple to execute with no side products and proceeding rapidly to high yield. Further, the thiol-ene reaction is most frequently photoinitiated, particularly for photopolymerizations resulting in highly uniform polymer networks, promoting unique capabilities related to spatial and temporal control of the click reaction. The reaction mechanism and its implementation in various synthetic methodologies, biofunctionalization, surface and polymer modification, and polymerization are all reviewed.

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          ‘Click’ Chemistry in Polymer and Materials Science

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            Thiol-enes: Chemistry of the past with promise for the future

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              Sequential Click Reactions for Synthesizing and Patterning 3D Cell Microenvironments

              Click chemistry provides extremely selective and orthogonal reactions that proceed with high efficiency and under a variety of mild conditions, the most common example being the copper(I)-catalyzed reaction of azides with alkynes1,2. While the versatility of click reactions has been broadly exploited3–5, a major limitation is the intrinsic toxicity of the synthetic schemes and the inability to translate these approaches to biological applications. This manuscript introduces a robust synthetic strategy where macromolecular precursors react via a copper-free click chemistry6, allowing for the direct encapsulation of cells within click hydrogels for the first time. Subsequently, an orthogonal thiol-ene photocoupling chemistry is introduced that enables patterning of biological functionalities within the gel in real-time and with micron-scale resolution. This material system allows one to tailor independently the biophysical and biochemical properties of the cell culture microenvironments in situ. This synthetic approach uniquely allows for the direct fabrication of biologically functionalized gels with ideal structures that can be photopatterned and all in the presence of cells.
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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angewandte Chemie International Edition
                Wiley
                14337851
                February 22 2010
                February 22 2010
                February 17 2010
                : 49
                : 9
                : 1540-1573
                Article
                10.1002/anie.200903924
                20166107
                d131f0b1-cd4b-4d89-afd8-c4ec1782c0d4
                © 2010

                http://doi.wiley.com/10.1002/tdm_license_1.1

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                Self URI (article page): http://doi.wiley.com/10.1002/anie.200903924

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