Thieno[3,2-b]thiophene flanked para-azaquinodimethane π-extended aromatic-quinoidal polymers

Bharath Dyaga; Witold Waliszewski; Zhitian Ling; Sasikumar Mayarambakam; Olivier Boyron; Wojciech Pisula; Bruno Schmaltz

doi:10.1016/j.synthmet.2024.117751

journal article·2024-12Open access

Thieno[3,2-b]thiophene flanked para-azaquinodimethane π-extended aromatic-quinoidal polymers

Bharath Dyaga, Witold Waliszewski, Zhitian Ling, Sasikumar Mayarambakam, Olivier Boyron, Wojciech Pisula, Bruno Schmaltz

Synthetic Metals· Volume 309

Publisher page Open full text

Source abstract

Abstract

A series of thieno[3,2- b ]thiophene (TT) flanked para -azaquinodimethane ( p -AQM) based quinoidal conjugated polymers PAQM2TT-T , PAQM2TT-BT and PAQM3TT were designed in a strategy to extend the aromatic-quinoidal π-system. The three polymers were synthesized by Stille polycondensation , and their opto-electronic properties and device performance in field-effect transistors have been explored. From absorption spectroscopy , the polymers show low bandgaps (1.54–1.57 eV) and high HOMO energy levels. They exhibit typical p-type behavior according to the results of the characterization of the field-effect transistors with average charge carrier mobilities of 0.08 cm 2 V −1 s −1 for PAQM2TT-T , 0.12 cm 2 V −1 s −1 for PAQM2TT-BT and 0.05 cm 2 V −1 s −1 for PAM3TT . This report presents an alternative π-extended quinoidal-donor strategy to control the molecular design and properties of new p -AQM-based conjugated polymers .

Source: openalex_inverted_index · Quality: baseline

Research context

Polymers Electronic materials

OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Photochromic and Fluorescence Chemistry

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (71)

Show source-provided references

1. Yu · Science · 1995 · 270 · 178910.1126/science.270.5243.1789 ↗

2. Yang · Chem · 2018 · 4 · 274810.1016/j.chempr.2018.08.005 ↗

3. Riede · Adv. Energy Mater. · 2021 · 1110.1002/aenm.202002653 ↗

4. Sirringhaus · Adv. Mater. · 2014 · 26 · 131910.1002/adma.201304346 ↗

5. Rivnay · Nat. Rev. Mater. · 2018 · 310.1038/natrevmats.2017.86 ↗

6. Li · Nat. Commun. · 2018 · 9 · 45110.1038/s41467-017-02805-5 ↗

7. Yamashita · Adv. Mater. · 2014 · 26 · 816910.1002/adma.201403767 ↗

8. Shi · Mater. Chem. Front. · 2017 · 1 · 242310.1039/C7QM00169J ↗

9. Yang · Adv. Mater. · 2019 · 31 · 190310410.1002/adma.201903104 ↗

10. Li · Adv. Mater. · 2016 · 28 · 943010.1002/adma.201602660 ↗

11. Beaujuge · J. Am. Chem. Soc. · 2011 · 133 · 2000910.1021/ja2073643 ↗

12. Zhao · Adv. Sci. · 2020 · 7

13. Xiong · Polym. Chem. · 2015 · 6 · 657910.1039/C5PY00804B ↗

14. Pattanasattayavong · RSC Adv. · 2014 · 4 · 5840410.1039/C4RA11487F ↗

15. Cho · Polym. Chem. · 2015 · 6 · 15010.1039/C4PY01112K ↗

16. Bijleveld · J. Mater. Chem. · 2011 · 21 · 922410.1039/c1jm10961h ↗

17. Chen · J. Polym. Sci., Part A: Polym. Chem. · 2014 · 52 · 197010.1002/pola.27204 ↗

18. Ponnappa · Polym. Chem. · 2019 · 10 · 372210.1039/C9PY00430K ↗

19. Sonar · J. Mater. Chem. · 2012 · 22 · 442510.1039/C2JM14989C ↗

20. Bronstein · J. Am. Chem. Soc. · 2011 · 133 · 327210.1021/ja110619k ↗

21. Shin · ACS Appl. Mater. Interfaces · 2015 · 7 · 328010.1021/am508026s ↗

22. Bronstein · Adv. Funct. Mater. · 2013 · 23 · 564710.1002/adfm.201300287 ↗

23. Ashraf · J. Am. Chem. Soc. · 2015 · 137 · 131410.1021/ja511984q ↗

24. Meager · J. Am. Chem. Soc. · 2013 · 135 · 1153710.1021/ja406934j ↗

25. Tandy · Org. Electron. · 2012 · 13 · 198110.1016/j.orgel.2012.05.046 ↗

26. Meager · Macromolecules · 2013 · 46 · 596110.1021/ma401128s ↗

27. Jung · Chem. Commun. · 2013 · 49 · 849510.1039/c3cc44676j ↗

28. Sun · Polym. Chem. · 2015 · 6 · 93810.1039/C4PY01193G ↗

29. Zhang · Polym. Chem. · 2015 · 6 · 477510.1039/C5PY00538H ↗

30. Guo · Adv. Funct. Mater. · 2018 · 180109710.1002/adfm.201801097 ↗

31. Yang · RSC Adv. · 2021 · 11 · 1299510.1039/D1RA00779C ↗

32. Yan · J. Am. Chem. Soc. · 2019 · 141 · 2021510.1021/jacs.9b10107 ↗

33. Hong · Synth. Met. · 2018 · 236 · 110.1016/j.synthmet.2017.12.013 ↗

34. Chen · Macromolecules · 2018 · 51 · 7110.1021/acs.macromol.7b00934 ↗

35. Meager · Adv. Funct. Mater. · 2014 · 24 · 710910.1002/adfm.201402307 ↗

36. Kim · Energy Environ. Sci. · 2014 · 7 · 411810.1039/C4EE02318H ↗

37. Wang · Macromolecules · 2012 · 45 · 120810.1021/ma202656b ↗

38. Kim · Energy Environ. Sci. · 2015 · 8 · 235210.1039/C5EE01627D ↗

39. Sun · Mater. Sci. Eng., R. · 2019 · 136 · 1310.1016/j.mser.2018.10.003 ↗

40. Huang · Macromolecules · 2019 · 52 · 474910.1021/acs.macromol.9b00370 ↗

41. Zhao · Macromolecules · 2021 · 54 · 349810.1021/acs.macromol.1c00124 ↗

42. Liu · Acc. Chem. Res. · 2023 · 56 · 166910.1021/acs.accounts.3c00214 ↗

43. Aswani Raj · J. Mater. Chem. C. · 2024 · 12 · 11010.1039/D3TC02233A ↗

44. Li · Macromol. Rapid Commun. · 2024 · 4510.1002/marc.202400276 ↗

45. Yuan · J. Am. Chem. Soc. · 2020 · 142 · 1003410.1021/jacs.0c01930 ↗

46. Deng · Angew. Chem. · 2016 · 55 · 345910.1002/anie.201508781 ↗

47. Zeng · J. Am. Chem. Soc. · 2015 · 137 · 857210.1021/jacs.5b04156 ↗

48. Yang · J. Am. Chem. Soc. · 2020 · 142 · 432910.1021/jacs.9b12683 ↗

49. Chung · ACS Appl. Mater. Interfaces · 2018 · 10 · 647110.1021/acsami.7b15584 ↗

50. Kim · Adv. Mater. · 2018 · 30

51. Cui · Macromolecules · 2011 · 44 · 786910.1021/ma2017293 ↗

52. Cui · Macromolecules · 2013 · 46 · 723210.1021/ma400008h ↗

53. Zhang · Polym. Chem. · 2014 · 5 · 375410.1039/C4PY00388H ↗

54. Hong · Chem. Commun. · 2013 · 49 · 48410.1039/C2CC37266E ↗

55. Kawabata · J. Am. Chem. Soc. · 2016 · 138 · 772510.1021/jacs.6b03688 ↗

56. Liu · J. Am. Chem. Soc. · 2017 · 139 · 835510.1021/jacs.7b04031 ↗

57. Yue · J. Mater. Chem. A · 2013 · 1 · 1011610.1039/c3ta12701j ↗

58. Wei · Adv. Funct. Mater. · 2021 · 31 · 201097910.1002/adfm.202010979 ↗

59. Liu · Adv. Funct. Mater. · 2018 · 28

60. Wang · J. Am. Chem. Soc. · 2020 · 142 · 1789210.1021/jacs.0c06604 ↗

61. Liu · J. Mater. Chem. A · 2021 · 9 · 2349710.1039/D1TA06383A ↗

62. Dyaga · Mater. Adv. · 2022 · 3 · 685310.1039/D2MA00628F ↗

63. Xiao · Mater. Adv. · 2023 · 4 · 192710.1039/D3MA00037K ↗

64. Osaka · J. Am. Chem. Soc. · 2009 · 131 · 252110.1021/ja801475h ↗

65. Wang · Adv. Mater. · 2020 · 32 · 200206010.1002/adma.202002060 ↗

66. Fu · Adv. Funct. Mater. · 2014 · 24 · 373410.1002/adfm.201304231 ↗

67. Yuan · Chem. Mater. · 2016 · 28 · 604510.1021/acs.chemmater.6b01929 ↗

68. Mikie · Chem. Mater. · 2021 · 33 · 818310.1021/acs.chemmater.1c02072 ↗

69. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian, Inc., Wallingford CT, 2013.

70. Yu · ACS Appl. Mater. Interfaces · 2017 · 9 · 4216710.1021/acsami.7b11863 ↗

71. Tam · Chem. Mater. · 2019 · 31 · 854310.1021/acs.chemmater.9b03684 ↗