Cycloadditions in modern polymer chemistry

Delaittre, G., Guimard, N. K., & Barner-Kowollik, C. (2015) Cycloadditions in modern polymer chemistry. Accounts of Chemical Research, 48(5).

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Abstract

ConspectusSynthetic polymer chemistry has undergone two major developments in the last two decades. About 20 years ago, reversible-deactivation radical polymerization processes started to give access to a wide range of polymeric architectures made from an almost infinite reservoir of functional building blocks. A few years later, the concept of click chemistry revolutionized the way polymer chemists approached synthetic routes. Among the few reactions that could qualify as click, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) initially stood out. Soon, many old and new reactions, including cycloadditions, would further enrich the synthetic macromolecular chemistry toolbox. Whether click or not, cycloadditions are in any case powerful tools for designing polymeric materials in a modular fashion, with a high level of functionality and, sometimes, responsiveness.Here, we wish to describe cycloaddition methodologies that have been reported in the last 10 years in the context of macromolecular engineering, with a focus on those developed in our laboratories. The overarching structure of this Account is based on the three most commonly encountered cycloaddition subclasses in organic and macromolecular chemistry: 1,3-dipolar cycloadditions, (hetero-)Diels-Alder cycloadditions ((H)DAC), and [2+2] cycloadditions. Our goal is to briefly describe the relevant reaction conditions, the advantages and disadvantages, and the realized polymer applications. Furthermore, the orthogonality of most of these reactions is highlighted because it has proven highly beneficial for generating unique, multifunctional polymers in a one-pot reaction.The overview on 1,3-dipolar cycloadditions is mostly centered on the application of CuAAC as the most travelled route, by far. Besides illustrating the capacity of CuAAC to generate complex polymeric architectures, alternative 1,3-dipolar cycloadditions operating without the need for a catalyst are described. In the area of (H)DA cycloadditions, beyond the popular maleimide/furan couple, we present chemistries based on more reactive species, such as cyclopentadienyl or thiocarbonylthio moieties, particularly stressing the reversibility of these systems. In these two greater families, as well as in the last section on [2+2] cycloadditions, we highlight phototriggered chemistries as a powerful tool for spatially and temporally controlled materials synthesis.Clearly, cycloaddition chemistry already has and will continue to transform the field of polymer chemistry in the years to come. Applying this chemistry enables better control over polymer composition, the development of more complicated polymer architectures, the simplification of polymer library production, and the discovery of novel applications for all of these new polymers. © 2015 American Chemical Society.

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ID Code: 99426
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :22
Export Date: 5 September 2016
CODEN: ACHRE
Correspondence Address: Delaittre, G.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, Germany
References: Braunecker, W.A., Matyjaszewski, K., Controlled/Living Radical Polymerization: Features, Developments, and Perspectives (2007) Prog. Polym. Sci., 32, pp. 93-146; Barner-Kowollik, C., (2008) Handbook of RAFT Polymerization, , Ed. Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim; Nicolas, J., Guillaneuf, Y., Lefay, C., Bertin, D., Gigmes, D., Charleux, B., Nitroxide-Mediated Polymerization (2013) Prog. Polym. Sci., 38, pp. 63-235; Kolb, H.C., Finn, M.G., Sharpless, K.B., Click Chemistry: Diverse Chemical Function from a Few Good Reactions (2001) Angew. Chem., Int. Ed., 40, pp. 2004-2021; Barner-Kowollik, C., Du Prez, F.E., Espeel, P., Hawker, C.J., Junkers, T., Schlaad, H., Van Camp, W., Clicking Polymers or Just Efficient Linking: What Is the Difference? (2011) Angew. Chem., Int. Ed., 50, pp. 60-62; Meldal, M., Polymer Clicking by CuAAC Reactions (2008) Macromol. Rapid Commun., 29, pp. 1016-1051; Volz, D., Baumann, T., Flugge, H., Mydlak, M., Grab, T., Bachle, M., Barner-Kowollik, C., Brase, S., Auto-Catalysed Crosslinking for Next-Generation OLED-Design (2012) J. Mater. Chem., 22, pp. 20786-20790; Wu, P., Feldman, A.K., Nugent, A.K., Hawker, C.J., Scheel, A., Voit, B., Pyun, J., Fokin, V.V., Efficiency and Fidelity in a Click-Chemistry Route to Triazole Dendrimers by the Copper(I)-Catalyzed Ligation of Azides and Alkynes (2004) Angew. Chem., Int. Ed., 43, pp. 3928-3932; Díaz, D.D., Punna, S., Holzer, P., McPherson, A.K., Sharpless, K.B., Fokin, V.V., Finn, M.G., Click Chemistry in Materials Synthesis. 1. Adhesive Polymers from Copper-Catalyzed Azide-Alkyne Cycloaddition (2004) J. Polym. Sci., Part A: Polym. Chem., 42, pp. 4392-4403; Schwartz, E., Breitenkamp, K., Fokin, V.V., Synthesis and Postpolymerization Functionalization of Poly(5-iodo-1,2,3-triazole)s (2011) Macromolecules, 44, pp. 4735-4741; Gerstel, P., Klumpp, S., Hennrich, F., Altintas, O., Eaton, T.R., Mayor, M., Barner-Kowollik, C., Kappes, M.M., Selective Dispersion of Single-Walled Carbon Nanotubes via Easily Accessible Conjugated Click Polymers (2012) Polym. Chem., 3, pp. 1966-1970; Lang, C., Pahnke, K., Kiefer, C., Goldmann, A.S., Roesky, P.W., Barner-Kowollik, C., Consecutive Modular Ligation As an Access Route to Palladium Containing Polymers (2013) Polym. Chem., 4, pp. 5456-5462; Lang, C., Voll, D., Inglis, A.J., Dingenouts, N., Goldmann, A.S., Barner, L., Barner-Kowollik, C., An Access Route to Polyferrocenes via Modular Conjugation (2011) Macromol. Chem. Phys., 212, pp. 831-839; Binauld, S., Fleury, E., Drockenmuller, E., Solving the Loss of Orthogonality during the Polyaddition of α-Azide-ω-Alkyne Monomers Catalyzed by Cu(PPh3)3Br: Application to the Synthesis of High-Molar Mass Polytriazoles (2010) J. Polym. Sci., Part A: Polym. Chem., 48, pp. 2470-2476; Qin, A., Lam, J.W.Y., Tang, B.Z., Click polymerization (2010) Chem. Soc. Rev., 39, pp. 2522-2544; Malkoch, M., Thibault, R.J., Drockenmuller, E., Messerschmidt, M., Voit, B., Russell, T.P., Hawker, C.J., Orthogonal Approaches to the Simultaneous and Cascade Functionalization of Macromolecules Using Click Chemistry (2005) J. Am. Chem. Soc., 127, pp. 14942-14949; Sumerlin, B.S., Tsarevsky, N.V., Louche, G., Lee, R.Y., Matyjaszewski, K., Highly Efficient Click Functionalization of Poly(3-azidopropyl methacrylate) Prepared by ATRP (2005) Macromolecules, 38, pp. 7540-7545; Ladmiral, V., Mantovani, G., Clarkson, G.J., Cauet, S., Irwin, J.L., Haddleton, D.M., Synthesis of Neoglycopolymers by a Combination of Click Chemistry and Living Radical Polymerization (2006) J. Am. Chem. Soc., 128, pp. 4823-4830; Kitto, H.J., Schwartz, E., Nijemeisland, M., Koepf, M., Cornelissen, J.J.L.M., Rowan, A.E., Nolte, R.J.M., Post-Modification of Helical Dipeptido Polyisocyanides Using the Click Reaction (2008) J. Mater. Chem., 18, pp. 5614-5624; Lang, C., Kiefer, C., Lejeune, E., Goldmann, A.S., Breher, F., Roesky, P.W., Barner-Kowollik, C., Palladium-Containing Polymers via a Combination of RAFT and Triazole Chemistry (2012) Polym. Chem., 3, pp. 2413-2420; Ladmiral, V., Legge, T.M., Zhao, Y., Perrier, S., Click Chemistry and Radical Polymerization: Potential Loss of Orthogonality (2008) Macromolecules, 41, pp. 6728-6732; Eisenblaetter, J., Bruns, M., Fehrenbacher, U., Barner, L., Barner-Kowollik, C., Synthesis of Polymers with Phosphorus Containing Side Chains via Modular Conjugation (2013) Polym. Chem., 4, pp. 2406-2413; Lang, A.S., Thelakkat, M., Modular Synthesis of Poly(perylene bisimides) Using Click Chemistry: A Comparative Study (2011) Polym. Chem., 2, pp. 2213-2221; Opsteen, J.A., Van Hest, J.C.M., Modular Synthesis of Block Copolymers via Cycloaddition of Terminal Azide and Alkyne Functionalized Polymers (2005) Chem. Commun., pp. 57-59; Quemener, D., Davis, T.P., Barner-Kowollik, C., Stenzel, M.H., RAFT and Click Chemistry: A Versatile Approach to Well-Defined Block Copolymers (2006) Chem. Commun., pp. 5051-5053; Willenbacher, J., Altintas, O., Roesky, P.W., Barner-Kowollik, C., Single-Chain Self-Folding of Synthetic Polymers Induced by Metal-Ligand Complexation (2014) Macromol. Rapid Commun., 35, pp. 45-51; Altintas, O., Tunca, U., Barner-Kowollik, C., Star and Miktoarm Star Block (Co)polymers via Self-Assembly of ATRP Generated Polymer Segments Featuring Hamilton Wedge and Cyanuric Acid Binding Motifs (2011) Polym. Chem., 2, pp. 1146-1155; Godula, K., Rabuka, D., Nam, K.T., Bertozzi, C.R., Synthesis and Microcontact Printing of Dual End-Functionalized Mucin-like Glycopolymers for Microarray Applications (2009) Angew. Chem., Int. Ed., 48, pp. 4973-4976; Durr, C.J., Emmerling, S.G.J., Lederhose, P., Kaiser, A., Brandau, S., Klimpel, M., Barner-Kowollik, C., High Molecular Weight Acrylonitrile-Butadiene Architectures via a Combination of RAFT Polymerization and Orthogonal Copper Mediated Azide-Alkyne Cycloaddition (2012) Polym. Chem., 3, pp. 1048-1060; Detrembleur, C., Debuigne, A., Altintas, O., Conradi, M., Wong, E.H.H., Jerome, C., Barner-Kowollik, C., Junkers, T., Synthesis of Star and H-Shape Polymers via a Combination of Cobalt-Mediated Radical Polymerization and Nitrone-Mediated Radical Coupling Reactions (2012) Polym. Chem., 3, pp. 135-147; Deiters, A., Cropp, T.A., Summerer, D., Mukherji, M., Schultz, P.G., Site-Specific PEGylation of Proteins Containing Unnatural Amino Acids (2004) Bioorg. Med. Chem. Lett., 14, pp. 5743-5745; Dirks, A.J., Cornelissen, J.J.L.M., Nolte, R.J.M., Monitoring Protein-Polymer Conjugation by a Fluorogenic Cu(I)-Catalyzed Azide-Alkyne 1,3-Dipolar Cycloaddition (2009) Bioconjugate Chem., 20, pp. 1129-1138; Gupta, S.S., Kuzelka, J., Singh, P., Lewis, W.G., Manchester, M., Finn, M.G., Accelerated Bioorthogonal Conjugation: A Practical Method for the Ligation of Diverse Functional Molecules to a Polyvalent Virus Scaffold (2005) Bioconjugate Chem., 16, pp. 1572-1579; Dirks, A.J., Van Berkel, S.S., Hatzakis, N.S., Opsteen, J.A., Van Delft, F.L., Cornelissen, J.J.L.M., Rowan, A.E., Nolte, R.J.M., Preparation of Biohybrid Amphiphiles via the Copper Catalysed Huisgen [3 + 2] Dipolar Cycloaddition Reaction (2005) Chem. Commun., pp. 4172-4174; Adzima, B.J., Tao, Y., Kloxin, C.J., Deforest, C.A., Anseth, K.S., Bowman, C.N., Spatial and Temporal Control of the Alkyne-Azide Cycloaddition by Photoinitiated Cu(II) Reduction (2011) Nat. Chem., 3, pp. 256-259; Wang, D.K., Rasoul, F., Hill, D.J.T., Hanson, G.R., Noble, C.J., Whittaker, A.K., The Role of Residual Cu(II) from Click-Chemistry in the Catalyzed Hydrolysis of Boltorn Polyester-Based Hydrogels (2012) Soft Matter, 8, pp. 435-445; Sletten, E.M., Bertozzi, C.R., From Mechanism to Mouse: A Tale of Two Bioorthogonal Reactions (2011) Acc. Chem. Res., 44, pp. 666-676; Dommerholt, J., Schmidt, S., Temming, R., Hendriks, L.J.A., Rutjes, F.P.J.T., Van Hest, J.C.M., Lefeber, D.J., Van Delft, F.L., Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells (2010) Angew. Chem., Int. Ed., 49, pp. 9422-9425; Canalle, L.A., Van Der Knaap, M., Overhand, M., Van Hest, J.C.M., A Comparison of Triazole-forming Bioconjugation Techniques for Constructing Comb-Shaped Peptide-Polymer Bioconjugates (2011) Macromol. Rapid Commun., 32, pp. 203-208; Clark, M., Kiser, P., In Situ Crosslinked Hydrogels Formed Using Cu(I)-Free Huisgen Cycloaddition Reaction (2009) Polym. Int., 58, pp. 1190-1195; Van Berkel, S.S., Dirks, A.J., Debets, M.F., Van Delft, F.L., Cornelissen, J.J.L.M., Nolte, R.J.M., Rutjes, F.P.J.T., Metal-Free Triazole Formation as a Tool for Bioconjugation (2007) ChemBioChem, 8, pp. 1504-1508; Williams, R.J., Barker, I.A., Oreilly, R.K., Dove, A.P., Orthogonal Modification of Norbornene-Functional Degradable Polymers (2012) ACS Macro Lett., 1, pp. 1285-1290; Ning, X., Temming, R.P., Dommerholt, J., Guo, J., Ania, D.B., Debets, M.F., Wolfert, M.A., Van Delft, F.L., Protein Modification by Strain-Promoted Alkyne-Nitrone Cycloaddition (2010) Angew. Chem., Int. Ed., 49, pp. 3065-3068; Lee, Y.-G., Yonekawa, M., Koyama, Y., Takata, T., Synthesis of a Kinetically Stabilized Homoditopic Nitrile N-Oxide Directed toward Catalyst-free Click Polymerization (2010) Chem. Lett., 39, pp. 420-421; Singh, I., Zarafshani, Z., Heaney, F., Lutz, J.-F., Orthogonal Modification of Polymer Chain-Ends via Sequential Nitrile Oxide-Alkyne and Azide-Alkyne Huisgen Cycloadditions (2011) Polym. Chem., 2, pp. 372-375; Lim, R.K.V., Lin, Q., Azirine Ligation: Fast and Selective Protein Conjugation via Photoinduced Azirine-Alkene Cycloaddition (2010) Chem. Commun., 46, pp. 7993-7995; Lim, R.K.V., Lin, Q., Bioorthogonal Chemistry: Recent Progress and Future Directions (2010) Chem. Commun., 46, pp. 1589-1600; Wang, T., Wu, Y., Kuan, S.L., Dumele, O., Lamla, M., Ng, D.Y.W., Arzt, M., Weil, T., A Disulfide Intercalator Toolbox for the Site-Directed Modification of Polypeptides (2015) Chem.-Eur. J., 21, pp. 228-238; Dietrich, M., Delaittre, G., Blinco, J.P., Inglis, A.J., Bruns, M., Barner-Kowollik, C., Photoclickable Surfaces for Profluorescent Covalent Polymer Coatings (2012) Adv. Funct. Mater., 22, pp. 304-312; Rodriguez-Emmenegger, C., Preuss, C.M., Yameen, B., Pop-Georgievski, O., Bachmann, M., Mueller, J.O., Bruns, M., Barner-Kowollik, C., Controlled Cell Adhesion on Poly(dopamine) Interfaces Photopatterned with Non-Fouling Brushes (2013) Adv. Mater., 25, pp. 6123-6127; Tischer, T., Rodriguez-Emmenegger, C., Trouillet, V., Welle, A., Schueler, V., Mueller, J.O., Goldmann, A.S., Barner-Kowollik, C., Photo-Patterning of Non-Fouling Polymers and Biomolecules on Paper (2014) Adv. Mater., 26, pp. 4087-4092; Mueller, J.O., Voll, D., Schmidt, F.G., Delaittre, G., Barner-Kowollik, C., Fluorescent Polymers from Non-Fluorescent Photoreactive Monomers (2014) Chem. Commun., 50, pp. 15681-15684; Diels, O., Alder, K., Synthesen in der hydroaromatischen Reihe (1928) Liebigs Ann. Chem., 460, pp. 98-122; Staudinger, H., Bruson, H.A., Hochpolymere Verbindungen. 7. Mitteilung. Über das Dicyclopentadien und weitere polymere Cyclopentadiene (1926) Liebigs Ann. Chem., 447, pp. 97-110; Schlicke, B., Schirmer, H., Schlüter, A.-D., Unsaturated Ladder Polymers: Structural Variations and Improved Molecular Weights (1995) Adv. Mater., 7, pp. 544-546; Adzima, B.J., Kloxin, C.J., Deforest, C.A., Anseth, K.S., Bowman, C.N., 3D Photofixation Lithography in Diels-Alder Networks (2012) Macromol. Rapid Commun., 33, pp. 2092-2096; Mantovani, G., Lecolley, F., Tao, L., Haddleton, D.M., Clerx, J., Cornelissen, J.J.L.M., Velonia, K., Design and Synthesis of N-Maleimido-Functionalized Hydrophilic Polymers via Copper-Mediated Living Radical Polymerization: A Suitable Alternative to PEGylation Chemistry (2005) J. Am. Chem. Soc., 127, pp. 2966-2973; Dag, A., Durmaz, H., Hizal, G., Tunca, U., Preparation of 3-Arm Star Polymers (A3) via Diels-Alder Click Reaction (2008) J. Polym. Sci., Part A: Polym. Chem., 46, pp. 302-313; Gandini, A., The Furan/Maleimide Diels-Alder Reaction: A Versatile Click-Unclick Tool in Macromolecular Synthesis (2013) Prog. Polym. Sci., 38, pp. 1-29; Inglis, A.J., Sinnwell, S., Stenzel, M.H., Barner-Kowollik, C., Ultrafast Click Conjugation of Macromolecular Building Blocks at Ambient Temperature (2009) Angew. Chem., Int. Ed., 48, pp. 2411-2414; Glassner, M., Kempe, K., Schubert, U.S., Hoogenboom, R., Barner-Kowollik, C., One-Pot Synthesis of Cyclopentadienyl Endcapped Poly(2-ethyl-2-oxazoline) and Subsequent Ambient Temperature Diels-Alder Conjugations (2011) Chem. Commun., 47, pp. 10620-10622; Inglis, A.J., Paulöhrl, T., Barner-Kowollik, C., Ambient Temperature Synthesis of a Versatile Macromolecular Building Block: Cyclopentadienyl-Capped Polymers (2009) Macromolecules, 43, pp. 33-36; Kavitha, A.A., Singha, N.K., Atom-Transfer Radical Copolymerization of Furfuryl Methacrylate (FMA) and Methyl Methacrylate (MMA): A Thermally-Amendable Copolymer (2007) Macromol. Chem. Phys., 208, pp. 2569-2577; Blinco, J.P., Trouillet, V., Bruns, M., Gerstel, P., Gliemann, H., Barner-Kowollik, C., Dynamic Covalent Chemistry on Surfaces Employing Highly Reactive Cyclopentadienyl Moieties (2011) Adv. Mater., 23, pp. 4435-4439; Nebhani, L., Barner-Kowollik, C., Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels-Alder Chemistry (2010) Macromol. Rapid Commun., 31, pp. 1298-1305; Zydziak, N., Hübner, C., Bruns, M., Barner-Kowollik, C., One-Step Functionalization of Single-Walled Carbon Nanotubes (SWCNTs) with Cyclopentadienyl-Capped Macromolecules via Diels-Alder Chemistry (2011) Macromolecules, 44, pp. 3374-3380; Nebhani, L., Sinnwell, S., Lin, C.Y., Coote, M.L., Stenzel, M.H., Barner-Kowollik, C., Strongly Electron Deficient Sulfonyldithioformate Based RAFT Agents for Hetero Diels-Alder Conjugation: Computational Design and Experimental Evaluation (2009) J. Polym. Sci., Part A: Polym. Chem., 47, pp. 6053-6071; Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., Ultra-Fast RAFT-HDA Click Conjugation: An Efficient Route to High Molecular Weight Block Copolymers (2009) Macromol. Rapid Commun., 30, pp. 1792-1798; Glassner, M., Delaittre, G., Kaupp, M., Blinco, J.P., Barner-Kowollik, C., (Ultra)Fast Catalyst-Free Macromolecular Conjugation in Aqueous Environment at Ambient Temperature (2012) J. Am. Chem. Soc., 134, pp. 7274-7277; Yameen, B., Rodriguez-Emmenegger, C., Ahmed, I., Preuss, C.M., Durr, C.J., Zydziak, N., Trouillet, V., Barner-Kowollik, C., A Facile One-Pot Route to Poly(carboxybetaine acrylamide) Functionalized SWCNTs (2013) Chem. Commun., 49, pp. 6734-6736; Espinosa, E., Glassner, M., Boisson, C., Barner-Kowollik, C., Dagosto, F., Synthesis of Cyclopentadienyl Capped Polyethylene and Subsequent Block Copolymer Formation Via Hetero Diels-Alder (HDA) Chemistry (2011) Macromol. Rapid Commun., 32, pp. 1447-1453; Billiet, S., De Bruycker, K., Driessen, F., Goossens, H., Van Speybroeck, V., Winne, J.M., Du Prez, F.E., Triazolinediones Enable Ultrafast and Reversible Click Chemistry for the Design of Dynamic Polymer Systems (2014) Nat. Chem., 6, pp. 815-821; Barker, I.A., Hall, D.J., Hansell, C.F., Du Prez, F.E., Oreilly, R.K., Dove, A.P., Tetrazine-Norbornene Click Reactions to Functionalize Degradable Polymers Derived from Lactide (2011) Macromol. Rapid Commun., 32, pp. 1362-1366; Hansell, C.F., Espeel, P., Stamenovic, M.M., Barker, I.A., Dove, A.P., Du Prez, F.E., Oreilly, R.K., Additive-Free Clicking for Polymer Functionalization and Coupling by Tetrazine-Norbornene Chemistry (2011) J. Am. Chem. Soc., 133, pp. 13828-13831; Inglis, A.J., Nebhani, L., Altintas, O., Schmidt, F.G., Barner-Kowollik, C., Rapid Bonding/Debonding on Demand: Reversibly Cross-Linked Functional Polymers via Diels-Alder Chemistry (2010) Macromolecules, 43, pp. 5515-5520; Oehlenschlaeger, K.K., Guimard, N.K., Brandt, J., Mueller, J.O., Lin, C.Y., Hilf, S., Lederer, A., Barner-Kowollik, C., Fast and Catalyst-Free Hetero-Diels-Alder Chemistry for on Demand Cyclable Bonding/Debonding Materials (2013) Polym. Chem., 4, pp. 4348-4355; Oehlenschlaeger, K.K., Mueller, J.O., Brandt, J., Hilf, S., Lederer, A., Wilhelm, M., Graf, R., Barner-Kowollik, C., Adaptable Hetero Diels-Alder Networks for Fast Self-Healing under Mild Conditions (2014) Adv. Mater., 26, pp. 3561-3566; Guimard, N.K., Ho, J., Brandt, J., Lin, C.Y., Namazian, M., Mueller, J.O., Oehlenschlaeger, K.K., Barner-Kowollik, C., Harnessing Entropy to Direct the Bonding/Debonding of Polymer Systems Based on Reversible Chemistry (2013) Chem. Sci., 4, pp. 2752-2759; Pahnke, K., Brandt, J., Grynova, G., Lindner, P., Schweins, R., Schmidt, F.G., Lederer, A., Barner-Kowollik, C., Entropy Driven Chain Effects on Ligation Chemistry (2015) Chem. Sci., 6, pp. 1061-1074; Guimard, N.K., Oehlenschlaeger, K.K., Zhou, J., Hilf, S., Schmidt, F.G., Barner-Kowollik, C., Current Trends in the Field of Self-Healing Materials (2012) Macromol. Chem. Phys., 213, pp. 131-143; Chen, X., Dam, M.A., Ono, K., Mal, A., Shen, H., Nutt, S.R., Sheran, K., Wudl, F., A Thermally Re-mendable Cross-Linked Polymeric Material (2002) Science, 295, pp. 1698-1702; Zhang, Y., Broekhuis, A.A., Picchioni, F., Thermally Self-Healing Polymeric Materials: The Next Step to Recycling Thermoset Polymers? (2009) Macromolecules, 42, pp. 1906-1912; Reutenauer, P., Buhler, E., Boul, P.J., Candau, S.J., Lehn, J.M., Room Temperature Dynamic Polymers Based on Diels-Alder Chemistry (2009) Chem.-Eur. J., 15, pp. 1893-1900; Paulöhrl, T., Inglis, A.J., Barner-Kowollik, C., Reversible Diels-Alder Chemistry as a Modular Polymeric Color Switch (2010) Adv. Mater., 22, pp. 2788-2791; Meador, M.A.B., Meador, M.A., Williams, L.L., Scheiman, D.A., Diels-Alder Trapping of Photochemically Generated Dienes with a Bismaleimide: A New Approach to Polyimide Synthesis (1996) Macromolecules, 29, pp. 8983-8986; Gruendling, T., Oehlenschlaeger, K.K., Frick, E., Glassner, M., Schmid, C., Barner-Kowollik, C., Rapid UV Light-Triggered Macromolecular Click Conjugations via the Use of o -Quinodimethanes (2011) Macromol. Rapid Commun., 32, pp. 807-812; Oehlenschlaeger, K.K., Mueller, J.O., Heine, N.B., Glassner, M., Guimard, N.K., Delaittre, G., Schmidt, F.G., Barner-Kowollik, C., Light-Induced Modular Ligation of Conventional RAFT Polymers (2013) Angew. Chem., Int. Ed., 52, pp. 762-766; Arumugam, S., Orski, S.V., Locklin, J., Popik, V.V., Photoreactive Polymer Brushes for High-Density Patterned Surface Derivatization Using a Diels-Alder Photoclick Reaction (2011) J. Am. Chem. Soc., 134, pp. 179-182; Glassner, M., Oehlenschlaeger, K.K., Gruendling, T., Barner-Kowollik, C., Ambient Temperature Synthesis of Triblock Copolymers via Orthogonal Photochemically and Thermally Induced Modular Conjugation (2011) Macromolecules, 44, pp. 4681-4689; Pauloehrl, T., Delaittre, G., Winkler, V., Welle, A., Bruns, M., Börner, H.G., Greiner, A.M., Barner-Kowollik, C., Adding Spatial Control to Click Chemistry: Phototriggered Diels-Alder Surface (Bio)functionalization at Ambient Temperature (2012) Angew. Chem., Int. Ed., 51, pp. 1071-1074; Richter, B., Pauloehrl, T., Kaschke, J., Fichtner, D., Fischer, J., Greiner, A.M., Wedlich, D., Bastmeyer, M., Three-Dimensional Microscaffolds Exhibiting Spatially Resolved Surface Chemistry (2013) Adv. Mater., 25, pp. 6117-6122; Hiltebrandt, K., Pauloehrl, T., Blinco, J.P., Linkert, K., Börner, H.G., Barner-Kowollik, C., λ-Orthogonal Pericyclic Macromolecular Photoligation (2015) Angew. Chem., Int. Ed., 54, pp. 2838-2843; Glassner, M., Oehlenschlaeger, K.K., Welle, A., Bruns, M., Barner-Kowollik, C., Polymer Surface Patterning via Diels-Alder Trapping of Photo-Generated Thioaldehydes (2013) Chem. Commun., 49, pp. 633-635; Zydziak, N., Feist, F., Huber, B., Mueller, J.O., Barner-Kowollik, C., Photo-Induced Sequence Defined Macromolecules via Hetero Bifunctional Synthons (2015) Chem. Commun., 51, pp. 1799-1802; Conradi, M., Junkers, T., Efficient [2 + 2] Photocycloadditions under Equimolar Conditions by Employing a Continuous UV-flow Reactor (2013) J. Photo Chem. Photobiol., A, 259, pp. 41-46; Conradi, M., Junkers, T., Fast and Efficient [2 + 2] UV Cycloaddition for Polymer Modification via Flow Synthesis (2014) Macromolecules, 47, pp. 5578-5585; Feng, P., Zhu, J., Cheng, Z., Zhang, Z., Zhu, X., Reversible Addition-Fragmentation Chain Transfer Polymerization of 7-(4-(Acryloyloxy)butoxy)coumarin (2007) Polymer, 48, pp. 5859-5866; Vo, C.D., Kuckling, D., Adler, H.J.P., Schönhoff, M., Preparation of Thermosensitive Nanogels by Photo-Cross-Linking (2002) Colloid Polym. Sci., 280, pp. 400-409; Murase, S., Kinoshita, K., Horie, K., Morino, S.Y., Photo-Optical Control with Large Refractive Index Changes by Photodimerization of Poly(vinyl cinnamate) Film (1997) Macromolecules, 30, pp. 8088-8090; Mizutani, M., Matsuda, T., Liquid Photocurable Biodegradable Copolymers: In Vivo Degradation of Photocured Poly(ν-caprolactone- co -trimethylene carbonate) (2002) J. Biomed. Mater. Res., 61, pp. 53-60; Conradi, M., Junkers, T., Photoinduced Conjugation of Aldehyde Functional Polymers with Olefins via [2 + 2]-Cycloaddition (2011) Macromolecules, 44, pp. 7969-7976
DOI: 10.1021/acs.accounts.5b00075
ISSN: 00014842
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 26 Sep 2016 02:55

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