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Combination of Photoinduced ATRP and Click Processes for the Synthesis of Triblock Copolymers

Yıl 2018, Cilt: 5 Sayı: 2, 727 - 736, 01.01.2018
https://doi.org/10.18596/jotcsa.414060

Öz

ABA type triblock
copolymers possessing polystyrene as middle segment and poly(ε-caprolactone)
(PCL) and poly(ethylene glycol) (PEG) as side segments were synthesized by
combining two photochemical strategies, namely photoinduced atom transfer
radical polymerization (ATRP) and click processes. For this purpose,
α,ω-diazido functional polystyrene (N3-PS-N3) was
synthesized by photoinduced ATRP using a bifunctional initiator, followed by a
simple substitution of the chain end halides. Parallel to this, alkyne-PCL was
synthesized by ring opening polymerization of ε-caprolactone, employing
propargyl alcohol as initiator. For the synthesis of alkyne-PEG, industrially
available PEG was functionalized by a simple esterification reaction using
5-pentynoic acid. After the syntheses of these alkyne functional polymers as
clickable counterparts, they were reacted with N3-PS-N3
by photoinduced click reactions to prepare the desired triblock copolymers. All
polymers were characterized by NMR, IR and GPC analyses.

Kaynakça

  • 1. Matyjaszewski K, Xia JH. Atom transfer radical polymerization. Chem Rev. 2001;101(9):2921-90.
  • 2. Chiefari J, Chong YK, Ercole F, Krstina J, Jeffery J, Le TPT, et al. Living free-radical polymerization by reversible addition-fragmentation chain transfer: The RAFT process. Macromolecules. 1998;31(16):5559-62.
  • 3. Moad G, Rizzardo E, Thang SH. Living radical polymerization by the RAFT process. Australian Journal of Chemistry. 2005;58(6):379-410.
  • 4. Hawker CJ, Bosman AW, Harth E. New polymer synthesis by nitroxide mediated living radical polymerizations. Chem Rev. 2001;101(12):3661-88.
  • 5. Coessens V, Pintauer T, Matyjaszewski K. Functional polymers by atom transfer radical polymerization. Prog Polym Sci. 2001;26(3):337-77.
  • 6. Matyjaszewski K. Atom Transfer Radical Polymerization (ATRP): Current Status and Future Perspectives. Macromolecules. 2012;45(10):4015-39.
  • 7. Pan X, Tasdelen MA, Laun J, Junkers T, Yagci Y, Matyjaszewski K. Photomediated controlled radical polymerization. Prog Polym Sci. 2016;62:73-125.
  • 8. Wang JS, Matyjaszewski K. CONTROLLED LIVING RADICAL POLYMERIZATION - HALOGEN ATOM-TRANSFER RADICAL POLYMERIZATION PROMOTED BY A CU(I)CU(II) REDOX PROCESS. Macromolecules. 1995;28(23):7901-10.
  • 9. Yilmaz G, Iskin B, Yagci Y. Photoinduced Copper( I)-Catalyzed Click Chemistry by the Electron Transfer Process Using Polynuclear Aromatic Compounds. Macromol Chem Phys. 2014;215(7):662-8.
  • 10. Pyun J, Kowalewski T, Matyjaszewski K. Synthesis of polymer brushes using atom transfer radical polymerization. Macromol Rapid Commun. 2003;24(18):1043-59.
  • 11. Gacal B, Durmaz H, Tasdelen MA, Hizal G, Tunca U, Yagci Y, et al. Anthracene-maleimide-based Diels-Alder "click chemistry" as a novel route to graft copolymers. Macromolecules. 2006;39(16):5330-6.
  • 12. Iskin B, Yilmaz G, Yagci Y. Synthesis of ABC type miktoarm star copolymers by triple click chemistry. Polym Chem. 2011;2(12):2865-71.
  • 13. Iskin B, Yilmaz G, Yagci Y. ABC Type Miktoarm Star Copolymers Through Combination of Controlled Polymerization Techniques with Thiol-ene and Azide-Alkyne Click Reactions. J Polym Sci, Part A: Polym Chem. 2011;49(11):2417-22.
  • 14. Kolb HC, Finn MG, Sharpless KB. Click chemistry: Diverse chemical function from a few good reactions. Angewandte Chemie-International Edition. 2001;40(11):2004-21.
  • 15. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angewandte Chemie-International Edition. 2002;41(14):2596-99.
  • 16. Gnanou Y, Hizal G. Effect of phenol and derivatives on atom transfer radical polymerization in the presence of air. J Polym Sci, Part A: Polym Chem. 2004;42(2):351-9.
  • 17. Matyjaszewski K, Jakubowski W, Min K, Tang W, Huang J, Braunecker WA, et al. Diminishing catalyst concentration in atom transfer radical polymerization with reducing agents. Proceedings of the National Academy of Sciences of the United States of America. 2006;103(42):15309-14.
  • 18. Tasdelen MA, Uygun M, Yagci Y. Photoinduced Controlled Radical Polymerization. Macromol Rapid Commun. 2011;32(1):58-62.
  • 19. Konkolewicz D, Schroder K, Buback J, Bernhard S, Matyjaszewski K. Visible Light and Sunlight Photoinduced ATRP with ppm of Cu Catalyst. Acs Macro Lett. 2012;1(10):1219-23.
  • 20. Tasdelen MA, Uygun M, Yagci Y. Studies on Photoinduced ATRP in the Presence of Photoinitiator. Macromol Chem Phys. 2011;212(18):2036-42.
  • 21. Tasdelen MA, Uygun M, Yagci Y. Photoinduced Controlled Radical Polymerization in Methanol. Macromol Chem Phys. 2010;211(21):2271-5.
  • 22. Shanmugam S, Boyer C. Stereo-, Temporal and Chemical Control through Photoactivation of Living Radical Polymerization: Synthesis of Block and Gradient Copolymers. J Am Chem Soc. 2015;137(31):9988-99.
  • 23. Shanmugam S, Xu J, Boyer C. Light-Regulated Polymerization under Near-Infrared/Far-Red Irradiation Catalyzed by Bacteriochlorophyll a. Angew Chem Int Ed Engl. 2016;55(3):1036-40.
  • 24. Tasdelen MA, Yilmaz G, Iskin B, Yagci Y. Photoinduced Free Radical Promoted Copper(I)-Catalyzed Click Chemistry for Macromolecular Syntheses. Macromolecules. 2012;45(1):56-61.
  • 25. Wang J-S, Matyjaszewski K. Controlled/"living" radical polymerization. atom transfer radical polymerization in the presence of transition-metal complexes. J Am Chem Soc. 1995;117(20):5614-5.
  • 26. Hoogenboom R, Moore BC, Schubert US. Synthesis of star-shaped poly(?-caprolactone) via 'click' chemistry and 'supramolecular click' chemistry. Chem Commun. 2006(38):4010-2.
  • 27. Jerome C, Lecomte P. Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization. Advanced drug delivery reviews. 2008;60(9):1056-76.
  • 28. Dursun C, Degirmenci M, Yagci Y, Jockusch S, Turro NJ. Free radical promoted cationic polymerization by using bisacylphosphine oxide photoinitiators: substituent effect on the reactivity of phosphinoyl radicals. Polymer. 2003;44(24):7389-96.
  • 29. Yagci Y, Tasdelen MA, Jockusch S. Reduction of Cu(II) by photochemically generated phosphonyl radicals to generate Cu(I) as catalyst for atom transfer radical polymerization and azide-alkyne cycloaddition click reactions. Polymer. 2014;55(16):3468-74.
Yıl 2018, Cilt: 5 Sayı: 2, 727 - 736, 01.01.2018
https://doi.org/10.18596/jotcsa.414060

Öz

Kaynakça

  • 1. Matyjaszewski K, Xia JH. Atom transfer radical polymerization. Chem Rev. 2001;101(9):2921-90.
  • 2. Chiefari J, Chong YK, Ercole F, Krstina J, Jeffery J, Le TPT, et al. Living free-radical polymerization by reversible addition-fragmentation chain transfer: The RAFT process. Macromolecules. 1998;31(16):5559-62.
  • 3. Moad G, Rizzardo E, Thang SH. Living radical polymerization by the RAFT process. Australian Journal of Chemistry. 2005;58(6):379-410.
  • 4. Hawker CJ, Bosman AW, Harth E. New polymer synthesis by nitroxide mediated living radical polymerizations. Chem Rev. 2001;101(12):3661-88.
  • 5. Coessens V, Pintauer T, Matyjaszewski K. Functional polymers by atom transfer radical polymerization. Prog Polym Sci. 2001;26(3):337-77.
  • 6. Matyjaszewski K. Atom Transfer Radical Polymerization (ATRP): Current Status and Future Perspectives. Macromolecules. 2012;45(10):4015-39.
  • 7. Pan X, Tasdelen MA, Laun J, Junkers T, Yagci Y, Matyjaszewski K. Photomediated controlled radical polymerization. Prog Polym Sci. 2016;62:73-125.
  • 8. Wang JS, Matyjaszewski K. CONTROLLED LIVING RADICAL POLYMERIZATION - HALOGEN ATOM-TRANSFER RADICAL POLYMERIZATION PROMOTED BY A CU(I)CU(II) REDOX PROCESS. Macromolecules. 1995;28(23):7901-10.
  • 9. Yilmaz G, Iskin B, Yagci Y. Photoinduced Copper( I)-Catalyzed Click Chemistry by the Electron Transfer Process Using Polynuclear Aromatic Compounds. Macromol Chem Phys. 2014;215(7):662-8.
  • 10. Pyun J, Kowalewski T, Matyjaszewski K. Synthesis of polymer brushes using atom transfer radical polymerization. Macromol Rapid Commun. 2003;24(18):1043-59.
  • 11. Gacal B, Durmaz H, Tasdelen MA, Hizal G, Tunca U, Yagci Y, et al. Anthracene-maleimide-based Diels-Alder "click chemistry" as a novel route to graft copolymers. Macromolecules. 2006;39(16):5330-6.
  • 12. Iskin B, Yilmaz G, Yagci Y. Synthesis of ABC type miktoarm star copolymers by triple click chemistry. Polym Chem. 2011;2(12):2865-71.
  • 13. Iskin B, Yilmaz G, Yagci Y. ABC Type Miktoarm Star Copolymers Through Combination of Controlled Polymerization Techniques with Thiol-ene and Azide-Alkyne Click Reactions. J Polym Sci, Part A: Polym Chem. 2011;49(11):2417-22.
  • 14. Kolb HC, Finn MG, Sharpless KB. Click chemistry: Diverse chemical function from a few good reactions. Angewandte Chemie-International Edition. 2001;40(11):2004-21.
  • 15. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angewandte Chemie-International Edition. 2002;41(14):2596-99.
  • 16. Gnanou Y, Hizal G. Effect of phenol and derivatives on atom transfer radical polymerization in the presence of air. J Polym Sci, Part A: Polym Chem. 2004;42(2):351-9.
  • 17. Matyjaszewski K, Jakubowski W, Min K, Tang W, Huang J, Braunecker WA, et al. Diminishing catalyst concentration in atom transfer radical polymerization with reducing agents. Proceedings of the National Academy of Sciences of the United States of America. 2006;103(42):15309-14.
  • 18. Tasdelen MA, Uygun M, Yagci Y. Photoinduced Controlled Radical Polymerization. Macromol Rapid Commun. 2011;32(1):58-62.
  • 19. Konkolewicz D, Schroder K, Buback J, Bernhard S, Matyjaszewski K. Visible Light and Sunlight Photoinduced ATRP with ppm of Cu Catalyst. Acs Macro Lett. 2012;1(10):1219-23.
  • 20. Tasdelen MA, Uygun M, Yagci Y. Studies on Photoinduced ATRP in the Presence of Photoinitiator. Macromol Chem Phys. 2011;212(18):2036-42.
  • 21. Tasdelen MA, Uygun M, Yagci Y. Photoinduced Controlled Radical Polymerization in Methanol. Macromol Chem Phys. 2010;211(21):2271-5.
  • 22. Shanmugam S, Boyer C. Stereo-, Temporal and Chemical Control through Photoactivation of Living Radical Polymerization: Synthesis of Block and Gradient Copolymers. J Am Chem Soc. 2015;137(31):9988-99.
  • 23. Shanmugam S, Xu J, Boyer C. Light-Regulated Polymerization under Near-Infrared/Far-Red Irradiation Catalyzed by Bacteriochlorophyll a. Angew Chem Int Ed Engl. 2016;55(3):1036-40.
  • 24. Tasdelen MA, Yilmaz G, Iskin B, Yagci Y. Photoinduced Free Radical Promoted Copper(I)-Catalyzed Click Chemistry for Macromolecular Syntheses. Macromolecules. 2012;45(1):56-61.
  • 25. Wang J-S, Matyjaszewski K. Controlled/"living" radical polymerization. atom transfer radical polymerization in the presence of transition-metal complexes. J Am Chem Soc. 1995;117(20):5614-5.
  • 26. Hoogenboom R, Moore BC, Schubert US. Synthesis of star-shaped poly(?-caprolactone) via 'click' chemistry and 'supramolecular click' chemistry. Chem Commun. 2006(38):4010-2.
  • 27. Jerome C, Lecomte P. Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization. Advanced drug delivery reviews. 2008;60(9):1056-76.
  • 28. Dursun C, Degirmenci M, Yagci Y, Jockusch S, Turro NJ. Free radical promoted cationic polymerization by using bisacylphosphine oxide photoinitiators: substituent effect on the reactivity of phosphinoyl radicals. Polymer. 2003;44(24):7389-96.
  • 29. Yagci Y, Tasdelen MA, Jockusch S. Reduction of Cu(II) by photochemically generated phosphonyl radicals to generate Cu(I) as catalyst for atom transfer radical polymerization and azide-alkyne cycloaddition click reactions. Polymer. 2014;55(16):3468-74.
Toplam 29 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Makaleler
Yazarlar

Gorkem Yilmaz 0000-0002-8638-4548

Yayımlanma Tarihi 1 Ocak 2018
Gönderilme Tarihi 10 Nisan 2018
Kabul Tarihi 18 Nisan 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 5 Sayı: 2

Kaynak Göster

Vancouver Yilmaz G. Combination of Photoinduced ATRP and Click Processes for the Synthesis of Triblock Copolymers. JOTCSA. 2018;5(2):727-36.