Ultrarapid Approaches to Mild Macromolecular Conjugation

Inglis, A. J. & Barner-Kowollik, C. (2011) Ultrarapid Approaches to Mild Macromolecular Conjugation. In Complex Macromolecular Architectures: Synthesis, Characterization, and Self-Assembly. John Wiley and Sons.

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Abstract

In light of the increasing demand for ultrarapid and mild conjugation chemistries for use in macromolecular chemistry, this chapter provides a critical overview of the very latest developments in this field. The principal aim, therefore, is the provision of a quick selection guide to aid in the formulation of a design strategy for novel functional materials and to provide recommendations for future developments in the chemistries discussed. © 2011 John Wiley & Sons (Asia) Pte Ltd.

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ID Code: 99273
Item Type: Book Chapter
Additional Information: Export Date: 5 September 2016
Correspondence Address: Inglis, A.J.; Preparative Macromolecular Chemistry, Karlsruhe Institute of Technology (KIT), Engesserstraße 18, Geb. 11.23, 76128 Karlsruhe, Germany
References: Agard, N.J., Prescher, J.A., Bertozzi, C.R., A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems (2004) Journal of the American Chemical Society, 126, p. 15046; Agard, N.J., Baskin, J.M., Prescher, J.A., Acomparative study of bioorthogonal reactions with azides (2006) ACS Chemical Biology, (1), p. 644; Bailey, W.J., (1972) Step Growth Polymerizations, 210, p. 987. , (ed.D.H. Solomon), Marcel Dekker, New York. Barner-Kowollik, C. and Inglis, A.J. (2009) Has click chemistry lead to a paradigm shift in polymer materials design? Macromolecular Chemistry and Physics; Baskin, J.M., Prescher, J.A., Laughlin, S.T., Copper-free click chemistry for dynamic in vivo imaging (2007) Proceedings of the National Academy of Sciences of the United States of America, 104, p. 16793; Becer, C.R., Hoogenboom, R., Schubert, U.S., Click chemistry beyond metal-catalyzed cycloaddition (2009) Angewandte Chemie-International Edition, 48, p. 4900; Bertin, A., Schlaad, H., Mild and versatile (bio-) functionalization of glass surfaces via thiol-ene photochemistry (2009) Chemistry of Materials, 21, p. 5698; Binder, W.H., Sachsenhofer, R., 'Click' chemistry in polymer and materials science: an update (2008) Macromolecular Rapid Communications, 29, p. 952; Blackman, M.L., Royzen, M., Fox, J.M., Tetrazine ligation: fast bioconjugation based on inverse-electrondemand Diels-Alder reactivity (2008) Journal of the American Chemical Society, 130, p. 13518; Braunecker, W.A., Matyjaszewski, K., Controlled/living radical polymerization: features, developments, and perspectives (2007) Progress in Polymer Science, 32, p. 93; Campos, L.M., Killops, K.L., Sakai, R., Development of thermal and photochemical strategies for thiol-ene click polymer functionalization (2008) Macromolecules, 41, p. 7063; Chan, J.W., Yu, B., Hoyle, C.E., Lowe, A.B., Convergent synthesis of 3-arm star polymers from RAFTprepared poly(N,N-diethylacrylamide) via a thiol-ene click reaction (2008) Chemical Communications, p. 4959; Chan, J.W., Hoyle, C.E., Lowe, A.B., Sequential phosphine-catalyzed, nucleophilic thiol-ene/radicalmediated thiol-yne reactions and the facile orthogonal synthesis of polyfunctional materials (2009) Journal of the American Chemical Society, 131, p. 5751; Chan, J.W., Yu, B., Hoyle, C.E., Lowe, A.B., The nucleophilic, phosphine-catalyzed thiol-ene click reaction and convergent star synthesis with RAFT-prepared homopolymers (2009) Polymer, 50, p. 3158; Chen, G.J., Kumar, J., Gregory, A., Stenzel, M.H., Efficient synthesis of dendrimers via a thiol-yne and esterification process and their potential application in the delivery of platinum anti-cancer drugs (2009) Chemical Communications, p. 6291; Codelli, J.A., Baskin, J.M., Agard, N.J., Bertozzi, C.R., Second-generation difluorinated cyclooctynes for copper-free click chemistry (2008) Journal of the American Chemical Society, 130, p. 11486; Dag, A., Durmaz, H., Demir, E., Heterograft copolymers via double click reactions using one-pot technique (2008) Journal of Polymer Science Part A-Polymer Chemistry, 46, p. 6969; Dag, A., Durmaz, H., Tunca, U., Hizal, G., Multiarm star block copolymers via Diels-Alder click reaction (2009) Journal of Polymer Science Part A-Polymer Chemistry, 47, p. 178; Debets, M.F., van Berkel, S.S., Schoffelen, S., Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition (2010) Chemical Communications, 46, p. 97; Devaraj, N.K., Weissleder, R., Hilderbrand, S.A., Tetrazine-based cycloadditions: application to pretargeted live cell imaging (2008) Bioconjugate Chemistry, 19, p. 2297; Devaraj, N.K., Upadhyay, R., Hatin, J.B., Fast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition (2009) Angewandte Chemie-International Edition, 48, p. 7013; Durmaz, H., Colakoglu, B., Tunca, U., Hizal, G., Preparation of block copolymers via Diels-Alder reaction of maleimide- and anthracene-end functional polymers (2006) Journal of Polymer Science Part A-Polymer Chemistry, 44, p. 1667; Durmaz, H., Karatas, F., Tunca, U., Hizal, G., Preparation of ABC miktoarm star terpolymer containing poly(ethylene glycol), polystyrene, and poly(tert-butylacrylate) arms by combining Diels-Alder reaction, atom transfer radical, and stable free radical polymerization routes (2006) Journal ofPolymer SciencePart A-Polymer Chemistry, 44, p. 499; Durmaz, H., Dag, A., Altintas, O., One-pot synthesis of ABC type triblock copolymers via in situ click [3+2] and Diels-Alder [4+2] reactions (2007) Macromolecules, 40, p. 191; Fournier, D., Hoogenboom, R., Schubert, U.S., Clicking polymers: a straightforward approach to novel macromolecular architectures (2007) Chemical Society Reviews, 36, p. 1369; Gauthier, M.A., Gibson, M.I., Klok, H.A., Synthesis of functional polymers by post-polymerization modification (2009) Angewandte Chemie-International Edition, 48, p. 48; Gouin, S.G., Kovensky, J., A procedure for fast and regioselective copper-free click chemistry at room temperature with p-toluenesulfonyl alkyne (2009) Synlett, p. 1409; Grecian, S., Fokin, V.V., Ruthenium-catalyzed cycloaddition of nitrile oxides and alkynes: practical synthesis of isoxazoles (2008) Angewandte Chemie-International Edition, 47, p. 8285; Gress, A., Volkel, A., Schlaad, H., Thio-click modification of poly[2-(3-butenyl)-2-oxazoline] (2007) Macromolecules, 40, p. 7928; Grundmann, C., Frommeld, H.D., Nitrile oxides. 6. Some novel addition reactions of aromatic nitrile oxides (1966) The Journal of Organic Chemistry, 31, p. 157; Gungor, E., Hizal, G., Tunca, U., One-pot double click reactions for the preparation of H-shaped ABCDEtype quintopolymer (2009) Journal of Polymer Science Part A-Polymer Chemistry, 47, p. 3409; Gutsmiedl, K., Wirges, C.T., Ehmke, V., Carell, T., Copper-free "click" modification of DNA via nitrile oxide-norbornene 1,3-dipolar cycloaddition (2009) Organic Letters, 11, p. 2405; Hawker, C.J., Wooley, K.L., The convergence of synthetic organic and polymer chemistries (2005) Science, 309, p. 1200; Hay, J.N., Boyle, J.D., Parker, S.F., Wilson, D., Polymerization of N-phenylnadimide: a model for the crosslinking of PMR-15 polyimide (1989) Polymer, 30, p. 1032; Hensarling, R.M., Doughty, V.A., Chan, J.W., Patton, D.L., "Clicking" polymer brushes with thiol-yne chemistry: indoors and out (2009) Journal of the American Chemical Society, 131, p. 14673; Heredia, K.L., Tolstyka, Z.P., Maynard, H.D., Aminooxy end-functionalized polymers synthesized byATRP for chemoselective conjugation to proteins (2007) Macromolecules, 40, p. 4772; Himo, F., Lovell, T., Hilgraf, R., Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates (2005) Journal of the American Chemical Society, 127, p. 210; Hoyle, C.E., Lee, T.Y., Roper, T., Thiol-enes: chemistry of the past with promise for the future (2004) Journal of Polymer Science Part a-Polymer Chemistry, 42, p. 5301; Inglis, A.J., Sinnwell, S., Davis, T.P., Reversible addition fragmentation chain transfer (RAFT) and hetero-Diels-Alder chemistry as a convenient conjugation tool for access to complex macromolecular designs (2008) Macromolecules, 41, p. 4120; Inglis, A.J., Sinnwell, S., Stenzel, M.H., Kowollik, B.C., Ultrafast click conjugation of macromolecular building blocks at ambient temperature (2009) Angewandte Chemie-International Edition, 48, p. 2411; Inglis, A.J., Paulöhrl, T., Kowollik, B.C., Ambient temperature synthesis of a versatile macromolecular building block: cyclopentadienyl-capped polymers (2009) Macromolecules, 43, p. 33; Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., Ultra-fastRAFT-HDAclick conjugation: an efficient route to high molecular weight block copolymers (2009) Macromolecular Rapid Communications, 30, p. 1792; Kamahori, F.K., Tada, S., Ito, K., Itsuno, S., Optically active polymer synthesis by Diels-Alder polymerization with chirally modified Lewis acid catalyst (1999) Macromolecules, 32, p. 541; Killops, K.L., Campos, L.M., Hawker, C.J., Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry (2008) Journal of the American Chemical Society, 130, p. 5062; Klemm, E., Stöckl, C., Synthesis of SH- and NCO- terminated thiocarbamate prepolymers (1991) Makromolekulare Chemie-Macromolecular Chemistry and Physics, 192, p. 153; Köhn, M., Breinbauer, R., The Staudinger ligation-a gift to chemical biology (2004) Angewandte Chemie- International Edition, 43, p. 3106; Kolb, H.C., Finn, M.G., Sharpless, K.B., Click chemistry: diverse chemical function from a few good reactions (2001) Angewandte Chemie-International Edition, 40, p. 2004; Konkolewicz, D., Gray-Weale, A., Perrier, S., Hyperbranched polymers by thiol-yne chemistry: from small molecules to functional polymers (2009) Journal of the American Chemical Society, 131, p. 18075; Koo, S.P.S., Stamenovic, M.M., Prasath, A.R., Limitations of radical thiol-ene reactions for polymerpolymer conjugation (2010) Journal of Polymer Science Part A-Polymer Chemistry, 48, p. 1699; Koyama, Y., Yonekawa, M., Takata, T., Newclick chemistry: click polymerization via 1,3-dipolar addition of homo-ditopic aromatic nitrile oxides formed in situ (2008) Chemistry Letters, 37, p. 918; Lee, Y.G., Koyama, Y., Yonekawa, M., Takata, T., Newclick chemistry: polymerization based on 1,3-dipolar cycloaddition of a homo ditopic nitrile N-oxide and transformation of the resulting polymers into reactive polymers (2009) Macromolecules, 42, p. 7709; Li, Z., Seo, T.S., Ju, J., 1,3-Dipolar cycloaddition of azides with electron-deficient alkynes under mild condition in water (2004) Tetrahedron Letters, 45, p. 3143; Li, H.B., Yu, B., Matsushima, H., The thiol-isocyanate click reaction: facile and quantitative access to omega-end-functional poly(N,N-diethylacrylamide) synthesized by RAFT radical polymerization (2009) Macromolecules, 42, p. 6537; Lowe, A.B., Thiol-ene "click" reactions and recent applications in polymer and materials synthesis (2010) Polymer Chemistry, 1, p. 17; Lutz, J.F., 1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science (2007) Angewandte Chemie-International Edition, 46, p. 1018; Lutz, J.F., Copper-free azide-alkyne cycloadditions: new insights and perspectives (2008) Angewandte Chemie- International Edition, 47, p. 2182; McKay, C.S., Moran, J., Pezacki, J.P., Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes (2010) Chemical Communications, 46, p. 931; Moad, G., Rizzardo, E., Thang, S.H., Radical addition-fragmentation chemistry in polymer synthesis (2008) Polymer, 49, p. 1079; Moad, G., Rizzardo, E., Thang, S.H., Living radical polymerization by the RAFT process-a second update (2009) Australian Journal of Chemistry, 62, p. 1402; Nebhani, L., Sinnwell, S., Inglis, A.J., Efficient surface modification of divinylbenzene microspheres via a combination of RAFT and hetero Diels-Alder chemistry (2008) Macromolecular Rapid Communications, 29, p. 1431; Nebhani, L., Sinnwell, S., Lin, C.Y., Strongly electron deficient sulfonyldithioformate based RAFTagents for hetero Diels-Alder conjugation: computational design and experimental evaluation (2009) Journal of Polymer Science Part A-Polymer Chemistry, 47, p. 6053; Nebhani, L., Gerstel, P., Atanasova, P., Efficient and mild modification of Si surfaces via orthogonal hetero Diels-Alder chemistry (2009) Journal of Polymer Science Part a-Polymer Chemistry, 47, p. 7090; Nenov, N., Koch, M., Klapper, M., Mullen, K., PEO-functionalized polystyrene as polymeric support in metallocene catalysed olefin polymerisation (2002) Polymer Bulletin, 47, p. 391; Ning, X.H., Guo, J., Wolfert, M.A., Boons, G.J., Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions (2008) Angewandte Chemie-International Edition, 47, p. 2253; Ouchi, M., Terashima, T., Sawamoto, M., Transition metal-catalyzed living radical polymerization: toward perfection in catalysis and precision polymer synthesis (2009) Chemical Reviews, 109, p. 4963; Pounder, R.J., Stanford, M.J., Brooks, P., Metal free thiol-maleimide 'Click' reaction as a mild functionalisation strategy for degradable polymers (2008) Chemical Communications, p. 5158; Quemener, D., Davis, T.P., Barner-Kowollik, C., Stenzel, M.H., RAFT and click chemistry: A versatile approach to well-defined block copolymers (2006) Chemical Communications, p. 5051; Rosen, B.M., Lligadas, G., Hahn, C., Percec, V., Synthesis of dendrimers through divergent iterative thiobromo "Click" chemistry (2009) Journal of Polymer Science Part A-Polymer Chemistry, 47, p. 3931; Rosen, B.M., Lligadas, G., Hahn, C., Percec, V., Synthesis of dendritic macromolecules through divergent iterative thio-bromo "Click" chemistry and SET-LRP (2009) Journal of Polymer Science Part A-Polymer Chemistry, 47, p. 3940; Royzen, M., Yap, G.P.A., Fox, J.M., A photochemical synthesis of functionalized trans-cyclooctynes driven by metal complexation (2008) Journal of the American Chemical Society, 130, p. 3760; Shao, H.Y., Crnogorac, M.M., Kong, T., Site-specific polymer attachment to a CCL-5 (RANTES) analogue by oxime exchange (2005) Journal of the American Chemical Society, 127, p. 1350; Shin, J., Matsushima, H., Chan, J.W., Hoyle, C.E., Segmented polythiourethane elastomers through sequential thiol-ene and thiol-isocyanate reactions (2009) Macromolecules, 42, p. 3294; Singh, I., Zarafshani, Z., Lutz, J.F., Heaney, F., Metal-free "click" chemistry: efficient polymer modification via 1,3-dipolar cycloaddition of nitrile oxides and alkynes (2009) Macromolecules, 42, p. 5411; Singh, I., Vyle, J.S., Heaney, F., Fast, copper-free click chemistry: a convenient solid-phase approach to oligonucleotide conjugation (2009) Chemical Communications, p. 3276; Sinnwell, S., Inglis, A.J., Davis, T.P., An atom-efficient conjugation approach to well-defined block copolymers using RAFT chemistry and hetero Diels-Alder cycloaddition (2008) Chemical Communications, p. 2052; Sinnwell, S., Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., Access to three-arm star block copolymers by a consecutive combination of the copper(I)-catalyzed azide-alkyne cycloaddition and the RAFT hetero Diels- Alder concept (2008) Macromolecular Rapid Communications, 29, p. 1090; Song, W., Wang, Y., Qu, J., A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins (2008) Angewandte Chemie-International Edition, 47, p. 2832; Song, W., Wang, Y., Qu, J., Lin, Q., Selective functionalization of a genetically encoded alkene-containing protein via "photoclick chemistry" in bacterial cells (2008) Journal of the American Chemical Society, 130, p. 9654; Stork, M., Koch, M., Klapper, M., Ethylene polymerization using crosslinked polystyrene as support for zirconocene dichloride/methylaluminoxane (1999) Macromolecular Rapid Communications, 20, p. 210; Sumerlin, B.S., Vogt, A.P., Macromolecular engineering through click chemistry and other efficient transformation (2010) Macromolecules, 43, p. 1; Ten Brummelhuis, N., Diehl, C., Schlaad, H., Thiol-ene modification of 1,2-polybutadiene using UV light or sunlight (2008) Macromolecules, 41, p. 9946; Watson, K.A., Bass, R.G., Polymer synthesis via a Diels-Alder reaction between bis(isobenzofuran)s and bis (phenylacetylene)s containing preformed phthalimide rings (2000) High Performance Polymers, 12, p. 299; Wittig, G., Krebs, A., Zur existenz niedergliedriger cycloalkine, I (1961) Chemische Berichte, 94, p. 3260; Xu, J., Tao, L., Boyer, C., Combining thio-bromo "click" chemistry and RAFT polymerization: a powerful tool for preparing functionalized multiblock and hyperbranched polymers (2010) Macromolecules., 43, p. 20
Keywords: Ambient temperature, Architecture, ATRP, Click chemistry, Conjugation, Copper-free, Modular, Polymers, RAFT, Rapid
DOI: 10.1002/9780470825150.ch2
ISBN: 9780470825136
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: 06 Oct 2016 00:42

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