Article
  • Synthesis and Characterization of Cyclopentadithiophene and Pyridylthiadiazole-based Polymers with Single and Double Bonds

  • Junghoon Lee†

  • Division of Chemical Engineering, Dongseo University, Busan 47011, Korea

  • Cyclopentadithiophene(CDT)과 Pyridylthiadiazole(PT)에 기반을 둔 단일결합과 이중결합을 갖는 전도성 고분자 합성 및 분석

  • 이정훈†

  • 동서대학교 화학공학부

  • Reproduction, stored in a retrieval system, or transmitted in any form of any part of this publication is permitted only by written permission from the Polymer Society of Korea.

References
  • 1. Moliton, A.; Hiorns, R. C. Review of Electronic and Optical Properties of Semiconducting π-conjugated Polymers: Applications in Optoelectronics. Polym. Int. 2004, 53, 1397-1412.
  •  
  • 2. Lu, H.; Li, X.; Lei, Q. Conjugated Conductive Polymer Materials and its Applications: A Mini-Review. Front. Chem. 2021, 9, 1-6.
  •  
  • 3. Nezakati, T.; Seifalian, A.; Tan, A.; Seifalian, A. M. Conductive Polymers: Opportunities and Challenges in Biomedical Applications. Chem. Rev. 2018, 118, 6766-6843.
  •  
  • 4. Facchetti, A. π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications. Chem. Mater. 2011, 23, 733-758.
  •  
  • 5. Lei, T.; Wang, J.-Y.; Pei, J. Design, Synthesis, and Structure-Property Relationships of Isoindigo-Based Conjugated Polymers. Acc. Chem. Res. 2014, 47, 1117-1126.
  •  
  • 6. Li, M.; An, C.; Pisula, W.; Müllen, K. Cyclopentadithiophene-Benzothiadiazole Donor-Acceptor Polymers as Prototypical Semiconductors for High-Performance Field-Effect Transistors. Acc. Chem. Res. 2018, 51, 1196-1205.
  •  
  • 7. Lee, J.; Cho, S.; Seo, J. W.; Anant, P.; Jacob, J.; Yang, C. Swapping Field-effect Transistor Characteristics in Polymeric Diketopyrrolopyrrole Semiconductors: Debut of An Electron Dominant Transporting Polymer. J. Mater. Chem. 2012, 22, 1504-1510.
  •  
  • 8. Ying, L.; Hsu, B. B. Y.; Zhan, H.; Welch, G. C.; Zalar, P.; Perez, L. A.; Kramer, E. J.; Nguyen, T.-Q.; Heeger, A. J.; Wong, W.-Y.; Bazan, G. C. Regioregular Pyridal[2,1,3]thiadiazole π-Conjugated Copolymers. J. Am. Chem. Soc. 2011, 133, 18538-18541.
  •  
  • 9. Anant, P.; Lucas, N. T.; Jacob, J. A Simple Route Toward the Synthesis of Bisbenzothiadiazole Derivatives. Org. Lett. 2008, 10, 5533-5536.
  •  
  • 10. Kim, J.; Yun, M. H.; Anant, P.; Cho, S.; Jacob, J.; Kim, J. Y.; Yang, C. Copolymers Comprising 2,7-Carbazole and Bis-benzothiadiazole Units for Bulk-Heterojunction Solar Cells. Chem.-Eur. J. 2011,17, 14681-14688.
  •  
  • 11. Taylor-Shaw, E.; Angioni, E.; Findlay, N. J.; Breig, B.; Inigo, A. R.; Bruckbauer, J.; Wallis, D. J.; Skabara, P. J.; Martin, R. W. Cool to Warm White Light Emission from Hybrid Inorganic/organic Light-emitting Diodes. J. Mater. Chem. C 2016, 4, 11499-11507.
  •  
  • 12. Bijleveld, J. C.; Shahid, M.; Gilot, J.; Wienk, M. M.; Janssen, R. A. J. Copolymers of Cyclopentadithiophene and Electron-Deficient Aromatic Units Designed for Photovoltaic Applications. Adv. Funct. Mater. 2009, 19, 3262-3270.
  •  
  • 13. Zhu, C.; Zhao, Z.; Chen, H.; Zheng, L.; Li, X.; Chen, J.; Sun, Y.; Liu, F.; Guo, Y.; Liu, Y. Regioregular Bis-Pyridal[2,1,3]thiadiazole-Based Semiconducting Polymer for High-Performance Ambipolar Transistors. J. Am. Chem. Soc. 2017, 139, 17735-17738.
  •  
  • 14. Liu, B.; Yu, W.-L.; Pei, J.; Liu, S.-Y.; Lai, Y.-H.; Huang, W. Design and Synthesis of Bipyridyl-Containing Conjugated Polymers: Effects of Polymer Rigidity on Metal Ion Sensing. Macromolecules 2001, 34, 7932-7940.
  •  
  • 15. Zhang, S.; Fan, H.; Liu, Y.; Zhao, G.; Li, Q.; Li, Y.; Zhan, X.Soluble Dithienothiophene Polymers: Effect of Link Pattern. J. Polym. Sci. A Polym. Chem. 2009, 47, 2843-2852.
  •  
  • 16. Ko, Y.-H.; Chandran, D.; Park, J.-G.; Lee, K.-S. Fluorene-based Conjugated Polymers Containing Acetylene Linkages for Photovoltaics. Mol. Cryst. Liq. Cryst. 2017, 655, 150-158.
  •  
  • 17. An, N.; Ran, H.; Geng, Y.; Zeng, Q.; Hu, J.; Yang, J.; Sun, Y.; Wang, X.; Zhou, E. Exploring a Fused 2-(Thiophen-2-yl)thieno [3,2-b]thiophene(T-TT) Building Block to Construct n-Type Polymer for High-Performance All-Polymer Solar Cells. ACS Appl. Mater. Interfaces 2019, 11, 42412-42419.
  •  
  • 18. Zhang, L.; Rose, B. D.; Liu, Y.; Nahid, M. M.; Gann, E.; Ly, J.; Zhao, W.; Rosa, S. J.; Russel, T. P.; Facchetti, A.; McNeill. C. R.; Brédas, J.-L.; Briseno, A. L. Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units. Chem. Mater. 2016, 28, 8580-8590.
  •  
  • 19. Kang, S.-H.; Tabi, G. D.; Lee, J.; Kim, G; Noh, Y.-Y.; Yang, C. Chlorinated 2,1,3-Benzothiadiazole-Based Polymers for Organic Field-Effect Transistors. Macromolecules 2017, 50, 4649-4657.
  •  
  • 20. Kim, G.; Kim, H.; Jang, M.; Jung, Y. K.; Oh, J. H.; Yang, C. Ultra-narrow-bandgap Thienoisoindigo Polymers: Structure-property Correlations in Field-effect Transistors. J. Mater. Chem. C 2016, 4, 9554-9560.
  •  
  • 21. Wang, Y.; Hasegawa, T.; Matsumoto, H.; Michinobu, T. Significant Improvement of Unipolar n-Type Transistor Performances by Manipulating the Coplanar Backbone Conformation of Electron-Deficient Polymers via Hydrogen Bonding. J. Am. Chem. Soc. 2019, 141, 3566-3575.
  •  
  • 22. Nakano, M.; Osaka, I.; Takimiya, K. Naphthodithiophene Diimide (NDTI)-Based Semiconducting Copolymers: From Ambipolar to Unipolar n-Type Polymers. Macromolecules 2015, 48, 576-584.
  •  
  • 23. Barford, W. Electronic and Optical Properties of Conjugated Polymers, 2nd Ed.; International Series of Monographs on Physics; Oxford Science Publications: Oxford, 2013; pp 1-305.
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2022 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2023; 47(4): 487-494

    Published online Jul 25, 2023

  • 10.7317/pk.2023.47.4.487
  • Received on Mar 3, 2023
  • Revised on Apr 14, 2023
  • Accepted on Apr 19, 2023

Correspondence to

  • Junghoon Lee

  • Division of Chemical Engineering, Dongseo University, Busan 47011, Korea

  • E-mail: junghoonlee@dongseo.ac.kr