Post-polymerization modification of pentafluorophenyl-functionalized polythioether via thiol-para-fluoro click reaction

References

• Staudinger, H.; Fritschi, J. Über Isopren und Kautschuk. 5. Mitteilung. über die hydrierung des kautschuks und über seine konstitution. Helv. Chim. Acta 1922, 5, 785–806. DOI: 10.1002/hlca.19220050517.
   Google Scholar
• Günay, K. A.; Theato, P.; Klok, H.-A. Standing on the Shoulders of Hermann Staudinger: Post-Polymerization Modification from past to Present. J. Polym. Sci. A Polym. Chem. 2013, 51, 1–28. DOI: 10.1002/pola.26333.
   Web of Science ®Google Scholar
• Goldmann, A. S.; Glassner, M.; Inglis, A. J.; Barner-Kowollik, C. Post-Functionalization of Polymers via Orthogonal Ligation Chemistry. Macromol. Rapid Commun. 2013, 34, 810–849. DOI: 10.1002/marc.201300017.
   PubMed Web of Science ®Google Scholar
• Blasco, E.; Sims, M. B.; Goldmann, A. S.; Sumerlin, B. S.; Barner-Kowollik, C. 50th Anniversary Perspective: Polymer Functionalization. Macromolecules 2017, 50, 5215–5252. DOI: 10.1021/acs.macromol.7b00465.
   Web of Science ®Google Scholar
• Stuparu, M. C.; Khan, A. Poly(ß-Hydroxy Thioether)s: Synthesis through Thiol-Epoxy ‘Click’ Reaction and Post-Polymerization Modification to Main-Chain Polysulfonium Salts. J. Macromol. Sci. Part A: Pure Appl. Chem. 2022, 59, 2–10. DOI: 10.1080/10601325.2021.1984849.
   Web of Science ®Google Scholar
• Macit, H.; Hazer, B. Grafting on Polybutadiene with Polytetrahydrofuran Macroperoxyinitiators. Postpolymerization Studies. Eur. Polym. J. 2007, 43, 3865–3872. DOI: 10.1016/j.eurpolymj.2007.06.023.
   Web of Science ®Google Scholar
• Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Ed. 2001, 40, 2004–2021. DOI: 10.1002/1521-3773.
   PubMed Web of Science ®Google Scholar
• Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem. 2002, 67, 3057–3064. DOI: 10.1021/jo011148j.
   PubMed Web of Science ®Google Scholar
• Geng, Z.; Shin, J. J.; Xi, Y.; Hawker, C. J. Click Chemistry Strategies for the Accelerated Synthesis of Functional Macromolecules. J. Polym. Sci. 2021, 59, 963–1042. DOI: 10.1002/pol.20210126.
   Web of Science ®Google Scholar
• Arslan, M.; Tasdelen, M. A. Click Chemistry in Macromolecular Design: Complex Architectures from Functional Polymers. Chem. Afr. 2019, 2, 195–214. DOI: 10.1007/s42250-018-0030-8.
   Google Scholar
• Durmaz, H.; Sanyal, A.; Hizal, G.; Tunca, U. Double Click Reaction Strategies for Polymer Conjugation and Post-Functionalization of Polymers. Polym. Chem. 2012, 3, 825–835. DOI: 10.1039/C1PY00471A.
   Web of Science ®Google Scholar
• Hizal, G.; Tunca, U.; Sanyal, A. Discrete Macromolecular Constructs via the Diels–Alder “Click” Reaction. J. Polym. Sci. A Polym. Chem. 2011, 49, 4103–4120. DOI: 10.1002/pola.24835.
   Web of Science ®Google Scholar
• Hoyle, C. E.; Lowe, A. B.; Bowman, C. N. Thiol-Click Chemistry: A Multifaceted Toolbox for Small Molecule and Polymer Synthesis. Chem. Soc. Rev. 2010, 39, 1355–1387. DOI: 10.1039/B901979K.
   PubMed Web of Science ®Google Scholar
• Lowe, A. B. Thiol-Ene “Click” Reactions and Recent Applications in Polymer and Materials Synthesis. Polym. Chem. 2010, 1, 17–36. DOI: 10.1039/B9PY00216B.
   Web of Science ®Google Scholar
• Mutlu, H.; Ceper, E. B.; Li, X.; Yang, J.; Dong, W.; Ozmen, M. M.; Theato, P. Sulfur Chemistry in Polymer and Materials Science. Macromol. Rapid Commun. 2019, 40, 1800650. DOI: 10.1002/marc.201800650.
   Web of Science ®Google Scholar
• Lowe, A. B. Thiol-Yne ‘Click’/Coupling Chemistry and Recent Applications in Polymer and Materials Synthesis and Modification. Polymer 2014, 55, 5517–5549. DOI: 10.1016/j.polymer.2014.08.015.
   Web of Science ®Google Scholar
• Kreye, O.; Tóth, T.; Meier, M. A. R. Introducing Multicomponent Reactions to Polymer Science: Passerini Reactions of Renewable Monomers. J. Am. Chem. Soc. 2011, 133, 1790–1792. DOI: 10.1021/ja1113003.
   PubMed Web of Science ®Google Scholar
• Tunca, U. Click and Multicomponent Reactions Work Together for Polymer Chemistry. Macromol. Chem. Phys. 2018, 219, 1800163. DOI: 10.1002/macp.201800163.
   Web of Science ®Google Scholar
• De, S.; Khan, A. Efficient Synthesis of Multifunctional Polymers via Thiol–Epoxy “Click” Chemistry. Chem. Commun. (Camb) 2012, 48, 3130–3132. DOI: 10.1039/C2CC30434A.
   PubMed Web of Science ®Google Scholar
• Chen, X.; Michinobu, T. Postpolymerization Modification: A Powerful Tool for the Synthesis and Function Tuning of Stimuli-Responsive Polymers. Macro Chem. Phys. 2022, 223, 2100370. DOI: 10.1002/macp.202100370.
   Web of Science ®Google Scholar
• Altintas, O.; Hizal, G.; Tunca, U. Synthesis of an ABCD 4-Miktoarm Star Quaterpolymer through a Diels–Alder Click Reaction. Des. Monomers Polym. 2009, 12, 83–98. DOI: 10.1163/156855508X391158.
   Web of Science ®Google Scholar
• Hazer, B. Simple Synthesis of Amphiphilic Poly(3-Hydroxy Alkanoate)s with Pendant Hydroxyl and Carboxylic Groups via Thiol-Ene Photo Click Reactions. Polym. Degrad. Stab. 2015, 119, 159–166. DOI: 10.1016/j.polymdegradstab.2015.04.024.
   Web of Science ®Google Scholar
• Cengiz, B.; Ejderyan, N.; Sanyal, A. Functional Polymeric Coatings: Thiol-Maleimide‘Click’chemistry as a Powerfulsurface Functionalization Tool. J. Macromol. Sci., Part A: Pure Appl. Chem. 2022, 59, 443–455. DOI: 10.1080/10601325.2022.2071725.
   Web of Science ®Google Scholar
• Öztürk, T.; Türkoğlu, H. Synthesis and Characterization of the Graft Copolymer Including Polyb-Butyrolactone and Polyvinyl Chloride by Ring-Opening Polymerization and“Click”Chemistry. J. Macromol. Sci., Part A: Pure Appl. Chem. 2022, 59, 872–879. DOI: 10.1080/10601325.2022.2143375.
   Web of Science ®Google Scholar
• Jackson, H. L. Fluoropolymers. J. Polym. Sci. B Polym. Lett. 1972, 10, 316–316. DOI: 10.1002/pol.1972.110100418.
   Google Scholar
• Agar, S.; Baysak, E.; Hizal, G.; Tunca, U.; Durmaz, H. An Emerging Post-Polymerization Modification Technique: The Promise of Thiol-Para-Fluoro Click Reaction. J. Polym. Sci. Part A: Polym. Chem. 2018, 56, 1181–1198. DOI: 10.1002/pola.29004.
   Web of Science ®Google Scholar
• Becer, C. R.; Babiuch, K.; Pilz, D.; Hornig, S.; Heinze, T.; Gottschaldt, M.; Schubert, U. S. Clicking Pentafluorostyrene Copolymers: Synthesis, Nanoprecipitation, and Glycosylation. Macromolecules 2009, 42, 2387–2394. DOI: 10.1021/ma9000176.
   Web of Science ®Google Scholar
• Becer, C. R.; Kokado, K.; Weber, C.; Can, A.; Chujo, Y.; Schubert, U. S. Metal-Free Synthesis of Responsive Polymers: Cloud Point Tuning by Controlled “Click” Reaction. J. Polym. Sci. A Polym. Chem. 2010, 48, 1278–1286. DOI: 10.1002/pola.23872.
   Web of Science ®Google Scholar
• Cakir, N.; Tunca, U.; Hizal, G.; Durmaz, H. Heterofunctionalized Multiarm Star Polymers via Sequential Thiol-Para-Fluoro and Thiol-Ene Double “Click” Reactions. Macromol. Chem. Phys. 2016, 217, 636–645. DOI: 10.1002/macp.201500300.
   Web of Science ®Google Scholar
• Delaittre, G.; Barner, L. The Para-Fluoro-Thiol Reaction as an Efficient Tool in Polymer Chemistry. Polym. Chem. 2018, 9, 2679–2684. DOI: 10.1039/C8PY00287H.
   Web of Science ®Google Scholar
• Baysak, E.; Tunca, U.; Hizal, G.; Durmaz, H. Preparation of Linear and Hyperbranched Fluorinated Poly(Aryl Ether-Thioether) through Para-Fluoro-Thiol Click Reaction. J. Polym. Sci. Part A: Polym. Chem. 2018, 56, 1853–1859. DOI: 10.1002/pola.29068.
   Web of Science ®Google Scholar
• Turgut, H.; Schmidt, A. C.; Wadhwani, P.; Welle, A.; Müller, R.; Delaittre, G. The Para-Fluoro-Thiol Ligation in Water. Polym. Chem. 2017, 8, 1288–1293. DOI: 10.1039/C6PY02108E.
   Web of Science ®Google Scholar
• Zhao, T.; Beyer, V. P.; Becer, C. R. Fluorinated Polymers via Para‐Fluoro‐Thiol and Thiol‐Bromo Click Step Growth Polymerization. Macromol. Rapid Commun. 2020, 41, 2000409. DOI: 10.1002/marc.202000409.
   Web of Science ®Google Scholar
• Zhao, T.; Drain, B.; Yilmaz, G.; Becer, C. R. One-Pot Synthesis of Amphiphilic Multiblock Poly(2-Oxazoline)s via Para-Fluoro-Thiol Click Reactions. Polym. Chem. 2021, 12, 6392–6403. DOI: 10.1039/D1PY00944C.
   Web of Science ®Google Scholar
• Wu, T.; Fitchett, C. M.; Downard, A. J. Para-Fluoro-Thiol Reaction on Anchor Layers Grafted from an Aryldiazonium Salt: A Tool for Surface Functionalization with Thiols. Langmuir 2021, 37, 11397–11405. DOI: 10.1021/acs.langmuir.1c02012.
   PubMed Web of Science ®Google Scholar
• Topcu, G.; Arenas, D. R.; Huband, S.; McNally, T.; Becer, C. R. Control over Microphase Separation and Dielectric Properties via Para-Fluoro Thiol Click Reaction. J. Mater. Chem. C 2022, 10, 9356–9363. DOI: 10.1039/D2TC00009A.
   Web of Science ®Google Scholar
• Mandal, P.; Marcasuzaa, P.; Billon, L. Para-Fluoro/Thiol Click Chemistry-Driven Pentafluorostyrene-Based Block Copolymer Self-Assembly: To Mimic or Not to Mimic the Solubility Parameter? Polym. Chem. 2022, 13, 4757–4762. DOI: 10.1039/D2PY00784C.
   Web of Science ®Google Scholar
• Du, Y.; Zeng, Q.; Yuan, L.; He, L. Post-Polymerization Modification Based on Reactive Fluorinated Polymers Reaction. J. Macromol. Sci., Part A: Pure Appl. Chem. 2021, 58, 521–538. DOI: 10.1080/10601325.2021.1903328.
   Web of Science ®Google Scholar
• Daglar, O.; Luleburgaz, S.; Baysak, E.; Gunay, U. S.; Hizal, G.; Tunca, U.; Durmaz, H. Nucleophilic Thiol-Yne Reaction in Macromolecular Engineering: From Synthesis to Applications. Eur. Polym. J. 2020, 137, 109926. DOI: 10.1016/j.eurpolymj.2020.109926.
   Web of Science ®Google Scholar
• Worch, J. C.; Stubbs, C. J.; Price, M. J.; Dove, A. P. Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-Yne, Amino-Yne, and Hydroxyl-Yne Reactions from (Bio)Organic to Polymer Chemistry. Chem. Rev. 2021, 121, 6744–6776. DOI: 10.1021/acs.chemrev.0c01076.
   PubMed Web of Science ®Google Scholar
• He, B.; Huang, J.; Liu, X.; Zhang, J.; Lam, J. W. Y.; Tang, B. Z. Polymerizations of Activated Alkynes. Prog. Polym. Sci. 2022, 126, 101503. DOI: 10.1016/j.progpolymsci.2022.101503.
   Web of Science ®Google Scholar
• Gunay, U. S.; Cetin, M.; Daglar, O.; Hizal, G.; Tunca, U.; Durmaz, H. Ultrafast and Efficient Aza-and thiol-Michael Reactions on a Polyester Scaffold with Internal Electron Deficient Triple Bonds. Polym. Chem. 2018, 9, 3037–3054. DOI: 10.1039/C8PY00485D.
   Web of Science ®Google Scholar
• Daglar, O.; Gunay, U. S.; Hizal, G.; Tunca, U.; Durmaz, H. Extremely Rapid Polythioether Synthesis in the Presence of TBD. Macromolecules 2019, 52, 3558–3572. DOI: 10.1021/acs.macromol.9b00293.
   Web of Science ®Google Scholar
• Daglar, O.; Çakmakçı, E.; Hizal, G.; Tunca, U.; Durmaz, H. Extremely Fast Synthesis of Polythioether Based Phase Change Materials (PCMs) for Thermal Energy Storage. Eur. Polym. J. 2020, 130, 109681. DOI: 10.1016/j.eurpolymj.2020.109681.
   Web of Science ®Google Scholar
• Daglar, O.; Cakmakci, E.; Gunay, U. S.; Hizal, G.; Tunca, U.; Durmaz, H. A Straightforward Method for Fluorinated Polythioether Synthesis. Macromolecules 2020, 53, 2965–2975. DOI: 10.1021/acs.macromol.0c00548.
   Web of Science ®Google Scholar
• Daglar, O.; Alkan, B.; Gunay, U. S.; Hizal, G.; Tunca, U.; Durmaz, H. Ultrafast Synthesis of Phosphorus-Containing Polythioethers in the Presence of TBD. Eur. Polym. J. 2022, 162, 110931. DOI: 10.1016/j.eurpolymj.2021.110931.
   Web of Science ®Google Scholar
• Lei, J. X.; Wang, Q. Y.; Du, F. S.; Li, Z. C. Dynamic Ring-Chain Equilibrium of Nucleophilic Thiol-Yne “Click” Polyaddition for Recyclable Poly(Dithioacetal)s. Chin. J. Polym. Sci. 2021, 39, 1146–1154. DOI: 10.1007/s10118-021-2587-y.
   Web of Science ®Google Scholar
• Zhang, J.; Zhang, Z.; Wang, J.; Zang, Q.; Sun, J. Z.; Tang, B. Z. Recent Progress in the Applications of Amino–Yne Click Chemistry. Polym. Chem. 2021, 12, 2978–2986. DOI: 10.1039/D1PY00113B.
   Web of Science ®Google Scholar
• He, B.; Su, H.; Bai, T.; Wu, Y.; Li, S.; Gao, M.; Hu, R.; Zhao, Z.; Qin, A.; Ling, J.; Tang, B. Z. Spontaneous Amino-Yne Click Polymerization: A Powerful Tool toward Regio- and Stereospecific Poly(β-Aminoacrylate)s. J. Am. Chem. Soc. 2017, 139, 5437–5443. DOI: 10.1021/jacs.7b00929.
   PubMed Web of Science ®Google Scholar
• Daglar, O.; Çakmakçi, E.; Gunay, U. S.; Hizal, G.; Tunca, U.; Durmaz, H. All in One: The Preparation of Polyester/Silica Hybrid Nanocomposites via Three Different Metal-Free Click Reactions. Eur. Polym. J. 2021, 154, 110532. DOI: 10.1016/j.eurpolymj.2021.110532.
   Web of Science ®Google Scholar
• Yildirimkaraman, O.; Özenler, S.; Gunay, U. S.; Durmaz, H.; Yıldız, Ü. H. Electroactive Nanogel Formation by Reactive Layer-by-Layer Assembly of Polyester and Branched Polyethylenimine via aza-Michael Addition. Langmuir 2021, 37, 10902–10913. DOI: 10.1021/acs.langmuir.1c01070.
   PubMed Web of Science ®Google Scholar
• Alkan, B.; Daglar, O.; Aydogan Temel, B.; Durmaz, H.; Temel, G. Rapid Synthesis of Polyester Based Single-Chain Polymeric Nanoparticles via an Intra-Molecular aza-Michael Addition Reaction. Polym. Chem. 2022, 13, 2442–2449. DOI: 10.1039/D1PY01631H.
   Web of Science ®Google Scholar
• Cetin, M.; Esen, C.; Daglar, O.; Luleburgaz, S.; Hizal, G.; Durmaz, H.; Tunca, U. 1, 3-Dipolar and Diels–Alder Cycloaddition Reactions on Polyester Backbones Possessing Internal Electron-Deficient Alkyne Moieties. Polym. Chem. 2016, 7, 7094–7100. DOI: 10.1039/C6PY01827K.
   Web of Science ®Google Scholar
• Pektas, B.; Sagdic, G.; Daglar, O.; Luleburgaz, S.; Gunay, U. S.; Hizal, G.; Tunca, U.; Durmaz, H. Ultrafast Synthesis of Dialkyne-Functionalized Polythioether and Post-Polymerization Modification via Click Chemistry. Polymer 2022, 253, 124989. DOI: 10.1016/j.polymer.2022.124989.
   Web of Science ®Google Scholar