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Photoproduction of High Molecular Weight Poly (N-methylpyrrole) under Green Conditions

Year 2023, , 443 - 452, 31.05.2023
https://doi.org/10.18596/jotcsa.1232989

Abstract

A novel and green photochemical polymerization method of N-methylpyrole is reported. Spectral and chromatographic characterizations revealed the formation of high molecular weight polymer (1436 kg/mol) having light absorption in the near-infrared region (~750 nm), high fluorescence emission in the visible region, high conductivity (0.062 S/cm) and good thermal stability. Powder X-ray diffractogram identified a totally amorphous polymer. According to cyclic voltammetry studies the polymer formed (PMPy) possess a relatively low electronic band gap (1.39 eV) which is very important for the (opto)electronic device applications of such materials.

Supporting Institution

İstanbul Teknik Üniversitesi

Thanks

Late Prof. Yusuf Yağcı

References

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  • 2. Nezakati T, Seifalian A, Tan A, Seifalian AM. Conductive Polymers: Opportunities and Challenges in Biomedical Applications. Chemical Reviews. 2018;118(14):6766-843.
  • 3. Prunet G, Pawula F, Fleury G, Cloutet E, Robinson AJ, Hadziioannou G, et al. A review on conductive polymers and their hybrids for flexible and wearable thermoelectric applications. Materials Today Physics. 2021;18:100402.
  • 4. R. Murad A, Iraqi A, Aziz SB, N. Abdullah S, Brza MA. Conducting Polymers for Optoelectronic Devices and Organic Solar Cells: A Review. Polymers. 2020;12(11):2627.
  • 5. Heck J, Goding J, Portillo Lara R, Green R. The influence of physicochemical properties on the processibility of conducting polymers: A bioelectronics perspective. Acta Biomaterialia. 2022;139:259-79.
  • 6. Wu X, Fu W, Chen H. Conductive Polymers for Flexible and Stretchable Organic Optoelectronic Applications. ACS Applied Polymer Materials. 2022;4(7):4609-23.
  • 7. Aradilla D, Estrany F, Casellas F, Iribarren JI, Alemán C. All-polythiophene rechargeable batteries. Organic Electronics. 2014;15(1):40-6.
  • 8. Yuan X, Zhao Y, Xie D, Pan L, Liu X, Duan C, et al. Polythiophenes for organic solar cells with efficiency surpassing 17%. Joule. 2022;6(3):647-61.
  • 9. Langer JJ, Ratajczak K, Frąckowiak E, Golczak S. Water-Induced Tuning of the Emission of Polyaniline LEDs within the NIR to Vis Range. ACS Omega. 2021;6(50):34650-60.
  • 10. Huang Y, Li H, Wang Z, Zhu M, Pei Z, Xue Q, et al. Nanostructured Polypyrrole as a flexible electrode material of supercapacitor. Nano Energy. 2016;22:422-38.
  • 11. Sengodu P. 12 - Conjugated polymers-based biosensors. In: Kumar V, Sharma K, Sehgal R, Kalia S, editors. Conjugated Polymers for Next-Generation Applications. 1: Woodhead Publishing; 2022. p. 401-46.
  • 12. Thadathil A, Pradeep H, Joshy D, Ismail YA, Periyat P. Polyindole and polypyrrole as a sustainable platform for environmental remediation and sensor applications. Materials Advances. 2022;3(7):2990-3022.
  • 13. Pang AL, Arsad A, Ahmadipour M. Synthesis and factor affecting on the conductivity of polypyrrole: a short review. Polymers for Advanced Technologies. 2021;32(4):1428-54.
  • 14. Tüken T, Tansuğ G, Yazıcı B, Erbil M. Poly(N-methyl pyrrole) and its copolymer with pyrrole for mild steel protection. Surface and Coatings Technology. 2007;202(1):146-54.
  • 15. Elibal F, Gumustekin S, Ozkazanc H, Ozkazanc E. Poly(N-methylpyrrole) with high antibacterial activity synthesized via interfacial polymerization method. Journal of Molecular Structure. 2021;1242:130712.
  • 16. Su W, Iroh JO. Electrodeposition mechanism, adhesion and corrosion performance of polypyrrole and poly(N-methylpyrrole) coatings on steel substrates. Synthetic Metals. 2000;114(3):225-34.
  • 17. Branzoi F, Mihai MA, Petrescu S. Corrosion Protection Efficacy of the Electrodeposit of Poly (N-Methyl Pyrrole-Tween20/3-Methylthiophene) Coatings on Carbon Steel in Acid Medium. Coatings. 2022;12(8):1062.
  • 18. Duran B, Bereket G. Cyclic Voltammetric Synthesis of Poly(N-methyl pyrrole) on Copper and Effects of Polymerization Parameters on Corrosion Performance. Industrial & Engineering Chemistry Research. 2012;51(14):5246-55.
  • 19. Ahmad S. Electropolymerization of poly(methyl pyrrole)/carbon nanotubes composites derived from ionic liquid. Polymer Engineering & Science. 2009;49(5):916-21.
  • 20. Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chemistry. 2001;3(4):156-64.
  • 21. Ustamehmetoğlu B, Kelleboz E. Oxidative Copolymerization of Pyrrole and N-Methyl Pyrrole. International Journal of Polymer Analysis and Characterization - Int J Polym Anal Charact. 2003;8:255-68.
  • 22. Dubitsky YA, Zhubanov BA, Maresch GG. Synthesis of polypyrroles in the presence of ferric tetrafluoroborate. Synthetic Metals. 1991;41(1):373-6.
  • 23. González-Tejera MJ, Martín G. Electrogeneration of Poly-N-Methylpyrrole Tosylate Doped Films. Electrochemical and Morphological Study. Portugaliae Electrochimica Acta. 2007;25:349-61.
  • 24. Genies EM, Syed AA. Polypyrrole and poly N-methylpyrrole — An electrochemical study in an aqueous medium. Synthetic Metals. 1984;10(1):21-30.
  • 25. Mahmoudian MR, Basirun WJ, Alias Y. Synthesis and characterization of poly(N-methylpyrrole)/TiO2 composites on steel. Applied Surface Science. 2011;257(8):3702-8.
  • 26. Kaya K, Yagci Y. Contemporary Approaches for Conventional and Light-Mediated Synthesis of Conjugated Heteroaromatic Polymers. Macromolecular Chemistry and Physics. 2021;222(24):2100334.
  • 27. Bagheri A, Jin J. Photopolymerization in 3D Printing. ACS Applied Polymer Materials. 2019;1(4):593-611.
  • 28. Zou D, Nunes SP, Vankelecom IFJ, Figoli A, Lee YM. Recent advances in polymer membranes employing non-toxic solvents and materials. Green Chemistry. 2021;23(24):9815-43.
  • 29. Somers P, Liang Z, Johnson JE, Boudouris BW, Pan L, Xu X. Rapid, continuous projection multi-photon 3D printing enabled by spatiotemporal focusing of femtosecond pulses. Light: Science & Applications. 2021;10(1):199.
  • 30. Malik MS, Schlögl S, Wolfahrt M, Sangermano M. Review on UV-Induced Cationic Frontal Polymerization of Epoxy Monomers. Polymers. 2020;12(9):2146.
  • 31. Shirai M. Photoinitiated Polymerization. In: Kobayashi S, Müllen K, editors. Encyclopedia of Polymeric Nanomaterials. Berlin, Heidelberg: Springer Berlin Heidelberg; 2015. p. 1579-85.
  • 32. Sari E, Yilmaz G, Koyuncu S, Yagci Y. Photoinduced Step-Growth Polymerization of N-Ethylcarbazole. Journal of the American Chemical Society. 2018;140(40):12728-31. 33. Kaya K, Koyuncu S, Yagci Y. Photoinduced synthesis of poly(N-ethylcarbazole) from phenacylium salt without conventional catalyst and/or monomer. Chemical Communications. 2019;55(77):11531-4.
  • 34. Yagci Y, Jockusch S, Turro NJ. Mechanism of Photoinduced Step Polymerization of Thiophene by Onium Salts:  Reactions of Phenyliodinium and Diphenylsulfinium Radical Cations with Thiophene. Macromolecules. 2007;40(13):4481-5.
  • 35. Celiker T, İsci R, Kaya K, Ozturk T, Yagci Y. Photoinduced step-growth polymerization of thieno[3,4-b] thiophene derivatives. The substitution effect on the reactivity and electrochemical properties. Journal of Polymer Science. 2020;58(17):2327-34.
  • 36. Hebert DD, Naley MA, Cunningham CC, Sharp DJ, Murphy EE, Stanton V, et al. Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes. Materials (Basel). 2021;14(20):6146.
  • 37. Abel SB, Frontera E, Acevedo D, Barbero CA. Functionalization of Conductive Polymers through Covalent Postmodification. Polymers. 2022;15(1):205.
  • 38. Kocaarslan A, Kaya K, Jockusch S, Yagci Y. Phenacyl Bromide as a Single-Component Photoinitiator: Photoinduced Step-Growth Polymerization of N-Methylpyrrole and N-Methylindole. Angewandte Chemie International Edition. 2022;61(36):e202208845.
  • 39. Kaya K. A green and fast method for PEDOT: Photoinduced step-growth polymerization of EDOT. Reactive and Functional Polymers. 2023;182:105464.
  • 40. Celiker T, Kaya K, Koyuncu S, Yagci Y. Polypyrenes by Photoinduced Step-Growth Polymerization. Macromolecules. 2020;53(14):5787-94.
Year 2023, , 443 - 452, 31.05.2023
https://doi.org/10.18596/jotcsa.1232989

Abstract

References

  • 1. K N, Rout CS. Conducting polymers: a comprehensive review on recent advances in synthesis, properties and applications. RSC Advances. 2021;11(10):5659-97.
  • 2. Nezakati T, Seifalian A, Tan A, Seifalian AM. Conductive Polymers: Opportunities and Challenges in Biomedical Applications. Chemical Reviews. 2018;118(14):6766-843.
  • 3. Prunet G, Pawula F, Fleury G, Cloutet E, Robinson AJ, Hadziioannou G, et al. A review on conductive polymers and their hybrids for flexible and wearable thermoelectric applications. Materials Today Physics. 2021;18:100402.
  • 4. R. Murad A, Iraqi A, Aziz SB, N. Abdullah S, Brza MA. Conducting Polymers for Optoelectronic Devices and Organic Solar Cells: A Review. Polymers. 2020;12(11):2627.
  • 5. Heck J, Goding J, Portillo Lara R, Green R. The influence of physicochemical properties on the processibility of conducting polymers: A bioelectronics perspective. Acta Biomaterialia. 2022;139:259-79.
  • 6. Wu X, Fu W, Chen H. Conductive Polymers for Flexible and Stretchable Organic Optoelectronic Applications. ACS Applied Polymer Materials. 2022;4(7):4609-23.
  • 7. Aradilla D, Estrany F, Casellas F, Iribarren JI, Alemán C. All-polythiophene rechargeable batteries. Organic Electronics. 2014;15(1):40-6.
  • 8. Yuan X, Zhao Y, Xie D, Pan L, Liu X, Duan C, et al. Polythiophenes for organic solar cells with efficiency surpassing 17%. Joule. 2022;6(3):647-61.
  • 9. Langer JJ, Ratajczak K, Frąckowiak E, Golczak S. Water-Induced Tuning of the Emission of Polyaniline LEDs within the NIR to Vis Range. ACS Omega. 2021;6(50):34650-60.
  • 10. Huang Y, Li H, Wang Z, Zhu M, Pei Z, Xue Q, et al. Nanostructured Polypyrrole as a flexible electrode material of supercapacitor. Nano Energy. 2016;22:422-38.
  • 11. Sengodu P. 12 - Conjugated polymers-based biosensors. In: Kumar V, Sharma K, Sehgal R, Kalia S, editors. Conjugated Polymers for Next-Generation Applications. 1: Woodhead Publishing; 2022. p. 401-46.
  • 12. Thadathil A, Pradeep H, Joshy D, Ismail YA, Periyat P. Polyindole and polypyrrole as a sustainable platform for environmental remediation and sensor applications. Materials Advances. 2022;3(7):2990-3022.
  • 13. Pang AL, Arsad A, Ahmadipour M. Synthesis and factor affecting on the conductivity of polypyrrole: a short review. Polymers for Advanced Technologies. 2021;32(4):1428-54.
  • 14. Tüken T, Tansuğ G, Yazıcı B, Erbil M. Poly(N-methyl pyrrole) and its copolymer with pyrrole for mild steel protection. Surface and Coatings Technology. 2007;202(1):146-54.
  • 15. Elibal F, Gumustekin S, Ozkazanc H, Ozkazanc E. Poly(N-methylpyrrole) with high antibacterial activity synthesized via interfacial polymerization method. Journal of Molecular Structure. 2021;1242:130712.
  • 16. Su W, Iroh JO. Electrodeposition mechanism, adhesion and corrosion performance of polypyrrole and poly(N-methylpyrrole) coatings on steel substrates. Synthetic Metals. 2000;114(3):225-34.
  • 17. Branzoi F, Mihai MA, Petrescu S. Corrosion Protection Efficacy of the Electrodeposit of Poly (N-Methyl Pyrrole-Tween20/3-Methylthiophene) Coatings on Carbon Steel in Acid Medium. Coatings. 2022;12(8):1062.
  • 18. Duran B, Bereket G. Cyclic Voltammetric Synthesis of Poly(N-methyl pyrrole) on Copper and Effects of Polymerization Parameters on Corrosion Performance. Industrial & Engineering Chemistry Research. 2012;51(14):5246-55.
  • 19. Ahmad S. Electropolymerization of poly(methyl pyrrole)/carbon nanotubes composites derived from ionic liquid. Polymer Engineering & Science. 2009;49(5):916-21.
  • 20. Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chemistry. 2001;3(4):156-64.
  • 21. Ustamehmetoğlu B, Kelleboz E. Oxidative Copolymerization of Pyrrole and N-Methyl Pyrrole. International Journal of Polymer Analysis and Characterization - Int J Polym Anal Charact. 2003;8:255-68.
  • 22. Dubitsky YA, Zhubanov BA, Maresch GG. Synthesis of polypyrroles in the presence of ferric tetrafluoroborate. Synthetic Metals. 1991;41(1):373-6.
  • 23. González-Tejera MJ, Martín G. Electrogeneration of Poly-N-Methylpyrrole Tosylate Doped Films. Electrochemical and Morphological Study. Portugaliae Electrochimica Acta. 2007;25:349-61.
  • 24. Genies EM, Syed AA. Polypyrrole and poly N-methylpyrrole — An electrochemical study in an aqueous medium. Synthetic Metals. 1984;10(1):21-30.
  • 25. Mahmoudian MR, Basirun WJ, Alias Y. Synthesis and characterization of poly(N-methylpyrrole)/TiO2 composites on steel. Applied Surface Science. 2011;257(8):3702-8.
  • 26. Kaya K, Yagci Y. Contemporary Approaches for Conventional and Light-Mediated Synthesis of Conjugated Heteroaromatic Polymers. Macromolecular Chemistry and Physics. 2021;222(24):2100334.
  • 27. Bagheri A, Jin J. Photopolymerization in 3D Printing. ACS Applied Polymer Materials. 2019;1(4):593-611.
  • 28. Zou D, Nunes SP, Vankelecom IFJ, Figoli A, Lee YM. Recent advances in polymer membranes employing non-toxic solvents and materials. Green Chemistry. 2021;23(24):9815-43.
  • 29. Somers P, Liang Z, Johnson JE, Boudouris BW, Pan L, Xu X. Rapid, continuous projection multi-photon 3D printing enabled by spatiotemporal focusing of femtosecond pulses. Light: Science & Applications. 2021;10(1):199.
  • 30. Malik MS, Schlögl S, Wolfahrt M, Sangermano M. Review on UV-Induced Cationic Frontal Polymerization of Epoxy Monomers. Polymers. 2020;12(9):2146.
  • 31. Shirai M. Photoinitiated Polymerization. In: Kobayashi S, Müllen K, editors. Encyclopedia of Polymeric Nanomaterials. Berlin, Heidelberg: Springer Berlin Heidelberg; 2015. p. 1579-85.
  • 32. Sari E, Yilmaz G, Koyuncu S, Yagci Y. Photoinduced Step-Growth Polymerization of N-Ethylcarbazole. Journal of the American Chemical Society. 2018;140(40):12728-31. 33. Kaya K, Koyuncu S, Yagci Y. Photoinduced synthesis of poly(N-ethylcarbazole) from phenacylium salt without conventional catalyst and/or monomer. Chemical Communications. 2019;55(77):11531-4.
  • 34. Yagci Y, Jockusch S, Turro NJ. Mechanism of Photoinduced Step Polymerization of Thiophene by Onium Salts:  Reactions of Phenyliodinium and Diphenylsulfinium Radical Cations with Thiophene. Macromolecules. 2007;40(13):4481-5.
  • 35. Celiker T, İsci R, Kaya K, Ozturk T, Yagci Y. Photoinduced step-growth polymerization of thieno[3,4-b] thiophene derivatives. The substitution effect on the reactivity and electrochemical properties. Journal of Polymer Science. 2020;58(17):2327-34.
  • 36. Hebert DD, Naley MA, Cunningham CC, Sharp DJ, Murphy EE, Stanton V, et al. Enabling Conducting Polymer Applications: Methods for Achieving High Molecular Weight in Chemical Oxidative Polymerization in Alkyl- and Ether-Substituted Thiophenes. Materials (Basel). 2021;14(20):6146.
  • 37. Abel SB, Frontera E, Acevedo D, Barbero CA. Functionalization of Conductive Polymers through Covalent Postmodification. Polymers. 2022;15(1):205.
  • 38. Kocaarslan A, Kaya K, Jockusch S, Yagci Y. Phenacyl Bromide as a Single-Component Photoinitiator: Photoinduced Step-Growth Polymerization of N-Methylpyrrole and N-Methylindole. Angewandte Chemie International Edition. 2022;61(36):e202208845.
  • 39. Kaya K. A green and fast method for PEDOT: Photoinduced step-growth polymerization of EDOT. Reactive and Functional Polymers. 2023;182:105464.
  • 40. Celiker T, Kaya K, Koyuncu S, Yagci Y. Polypyrenes by Photoinduced Step-Growth Polymerization. Macromolecules. 2020;53(14):5787-94.
There are 39 citations in total.

Details

Primary Language English
Subjects Polymer Science and Technologies
Journal Section RESEARCH ARTICLES
Authors

Kerem Kaya 0000-0002-5736-488X

Publication Date May 31, 2023
Submission Date January 12, 2023
Acceptance Date April 2, 2023
Published in Issue Year 2023

Cite

Vancouver Kaya K. Photoproduction of High Molecular Weight Poly (N-methylpyrrole) under Green Conditions. JOTCSA. 2023;10(2):443-52.