α,ω-Reactive Building Blocks Based on a Dual Functional RAFT Agent for Thermal and Light-Induced Ligation
Langer, M., Mueller, J. O., Goldmann, A. S., Schacher, F. H., & Barner-Kowollik, C. (2016) α,ω-Reactive Building Blocks Based on a Dual Functional RAFT Agent for Thermal and Light-Induced Ligation. ACS Macro Letters, 5(5).
A dual functional chain transfer agent (CTA) capable of highly efficient sequential thermal and photoinduced ligation, generating α,ω-functional polymers, is introduced. The newly designed CTA (1-(4-((2-formyl-3-methyl phenoxy)methyl)phenyl)ethyl (diethoxyphosphoryl)methane dithioate) fuses thermally triggered hetero Diels-Alder chemistry with rapid light-induced photoenol chemistry. The versatility of the CTA is exemplarily demonstrated via the preparation of an amphiphilic triblock quaterpolymer poly(isoprene-co-styrene)-block-poly(ethyl acrylate)-block-poly(ethylene oxide) (P(I-co-S)-b-PEA-b-PEO). Subsequent to the homopolymerization of ethyl acrylate (PEA), a Cp-functional poly(isoprene-co-styrene) (P(I-co-S)) is conjugated with the electron-deficient C - S double bond (dienophile) of the CTA end group, generating a P(I-co-S)-b-PEA diblock terpolymer. The triblock quaterpolymer P(I-co-S)-b-PEA-b-PEO is generated by photoligation of a macromolecular dienophile, i.e., the fumarate-terminated poly(ethylene oxide) (PEO-fum) to the photoenol-functional P(I-co-S)-b-PEA. The new dual functional ligation RAFT agent constitutes a technology platform for generating α,ω-reactive building blocks from one single chain transfer agent. © 2016 American Chemical Society.
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|Item Type:||Journal Article|
|Additional Information:||Export Date: 5 September 2016 Correspondence Address: Schacher, F.H.; Institute of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, Germany; email: firstname.lastname@example.org Funding Details: 031A119A, BMBF, Bundesministerium für Bildung und Forschung Funding Details: 031A119B, BMBF, Bundesministerium für Bildung und Forschung References: Chiefari, J., Chong, Y.K., Ercole, F., Krstina, J., Jeffery, J., Le, T.P.T., Mayadunne, R.T.A., Thang, S.H., Living Free-Radical Polymerization by Reversible Addition-Fragmentation Chain Transfer: The RAFT Process (1998) Macromolecules, 31, pp. 5559-5562; Keddie, D.J., A guide to the synthesis of block copolymers using reversible-addition fragmentation chain transfer (RAFT) polymerization (2014) Chem. Soc. Rev., 43, pp. 496-505; Barner-Kowollik, C., (2008) Handbook of RAFT Polymerization, , Wiley-VCH: Weinheim; Iha, R.K., Wooley, K.L., Nyström, A.M., Burke, D.J., Kade, M.J., Hawker, C.J., Applications of Orthogonal Click Chemistries in the Synthesis of Functional Soft Materials (2009) Chem. Rev., 109, pp. 5620-5686; Schacher, F.H., Rupar, P.A., Manners, I., Functional Block Copolymers: Nanostructured Materials with Emerging Applications (2012) Angew. Chem., Int. Ed., 51, pp. 7898-7921; Laus, M., Papa, R., Sparnacci, K., Alberti, A., Benaglia, M., Macciantelli, D., Controlled Radical Polymerization of Styrene with Phosphoryl- and (Thiophosphoryl)dithioformates as RAFT Agents (2001) Macromolecules, 34, pp. 7269-7275; Sammes, P.G., Photoenolisation (1976) Tetrahedron, 32, pp. 405-422; Sinnwell, S., Inglis, A.J., Davis, T.P., Stenzel, M.H., Barner-Kowollik, C., An atom-efficient conjugation approach to well-defined block copolymers using RAFT chemistry and hetero Diels-Alder cycloaddition (2008) Chem. Commun., pp. 2052-2054; 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; Hirschbiel, A.F., Schmidt, B.V.K.J., Krolla-Sidenstein, P., Blinco, J.P., Barner-Kowollik, C., Photochemical Design of Stimuli-Responsive Nanoparticles Prepared by Supramolecular Host-Guest Chemistry (2015) Macromolecules, 48, pp. 4410-4420; Kropp, P.J., Daus, K.A., Crawford, S.D., Tubergen, M.W., Kepler, K.D., Craig, S.L., Wilson, V.P., Surface-Mediated Reactions. 1. Hydrohalogenation of Alkenes and Alkynes (1990) J. Am. Chem. Soc., 112, pp. 7433-7434; Langer, M., Brandt, J., Lederer, A., Goldmann, A.S., Schacher, F.H., Barner-Kowollik, C., Amphiphilic Block Copolymers Featuring a Reversible Hetero Diels-Alder Linkage (2014) Polym. Chem., 5, pp. 5330-5338; Barner-Kowollik, C., On the Quantitative Click Conjugation of Molecular Weight Distributions: What can Theoretically be Expected ? (2009) Macromol. Rapid Commun., 30, pp. 1625-1631|
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|Deposited On:||22 Sep 2016 04:50|
|Last Modified:||23 Sep 2016 04:15|
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