From p- to n-Type Mixed Conduction in Isoindigo-Based Polymers through Molecular Design.
donor-acceptor polymers
isoindigo
mixed conductors
organic bioelectronics
semiconducting polymers
Journal
Advanced materials (Deerfield Beach, Fla.)
ISSN: 1521-4095
Titre abrégé: Adv Mater
Pays: Germany
ID NLM: 9885358
Informations de publication
Date de publication:
Apr 2022
Apr 2022
Historique:
revised:
06
12
2021
received:
30
09
2021
pubmed:
26
1
2022
medline:
26
1
2022
entrez:
25
1
2022
Statut:
ppublish
Résumé
Organic mixed ionic and electronic conductors are of significant interest for bioelectronic applications. Here, three different isoindigoid building blocks are used to obtain polymeric mixed conductors with vastly different structural and electronic properties which can be further fine-tuned through the choice of comonomer unit. This work shows how careful design of the isoindigoid scaffold can afford highly planar polymer structures with high degrees of electronic delocalization, while subtle structural modifications can control the dominant charge carrier (hole or electron) when probed in organic electrochemical transistors. A combination of experimental and computational techniques is employed to probe electrochemical, structural, and mixed ionic and electronic properties of the polymer series which in turn allows the derivation of important structure-property relations for this promising class of materials in the context of organic bioelectronics. Ultimately, these findings are used to outline robust molecular-design strategies for isoindigo-based mixed conductors that can support efficient p-type, n-type, and ambipolar transistor operation in an aqueous environment.
Identifiants
pubmed: 35075720
doi: 10.1002/adma.202107829
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2107829Subventions
Organisme : Academy of Medical Sciences & Wellcome Trust
ID : SBF002/1158
Organisme : Materials Research Institute
Organisme : National Science Foundation
ID : NSF DMR-1751308
Organisme : Advanced Photon Source
Organisme : U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory
Organisme : Northwestern University Micro/Nano Fabrication Facility
Organisme : Soft and Hybrid Nanotechnology Experimental
ID : NSF ECCS-1542205
Organisme : Materials Research Science and Engineering Center
ID : DMR-1720139
Organisme : State of Illinois, and Northwestern University
Organisme : Keck-II and EPIC facilities of Northwestern University's NUANCE Center
Organisme : Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource
ID : NSF ECCS-1542205
Organisme : Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource
ID : NSF DMR-1720139
Organisme : Materials Research Center
Organisme : International Institute for Nanotechnology
Informations de copyright
© 2022 The Authors. Advanced Materials published by Wiley-VCH GmbH.
Références
M. Berggren, A. Richter-Dahlfors, Adv. Mater. 2007, 19, 3201.
T. Someya, Z. Bao, G. G. Malliaras, Nature 2016, 540, 379.
B. D. Paulsen, K. Tybrandt, E. Stavrinidou, J. Rivnay, Nat. Mater. 2020, 19, 13.
J. Rivnay, P. Leleux, M. Sessolo, D. Khodagholy, T. Hervé, M. Fiocchi, G. G. Malliaras, Adv. Mater. 2013, 25, 7010.
S. T. Keene, T. P. A. van der Pol, D. Zakhidov, C. H. L. Weijtens, R. A. J. Janssen, A. Salleo, Y. van de Burgt, Adv. Mater. 2020, 32, 2000270.
P. Jastrzebska-Perfect, G. D. Spyropoulos, C. Cea, Z. Zhao, O. J. Rauhala, A. Viswanathan, S. A. Sheth, J. N. Gelinas, D. Khodagholy, Sci. Adv. 2020, 6, eaaz6767.
Y. Kim, H. Noh, B. D. Paulsen, J. Kim, I. Y. Jo, H. J. Ahn, J. Rivnay, M. H. Yoon, Adv. Mater. 2021, 33, 2007550.
C. B. Nielsen, A. Giovannitti, D.-T. T. Sbircea, E. Bandiello, M. R. Niazi, D. A. Hanifi, M. Sessolo, A. Amassian, G. G. Malliaras, J. Rivnay, I. Mcculloch, J. Am. Chem. Soc. 2016, 138, 10252.
A. Giovannitti, D.-T. Sbircea, S. Inal, C. B. Nielsen, E. Bandiello, D. A. Hanifi, M. Sessolo, G. G. Malliaras, I. McCulloch, J. Rivnay, Proc. Natl. Acad. Sci. USA 2016, 113, 12017.
E. Zeglio, J. Eriksson, R. Gabrielsson, N. Solin, O. Inganäs, Adv. Mater. 2017, 29, 1605787.
T. Nicolini, J. Surgailis, A. Savva, A. D. Scaccabarozzi, R. Nakar, D. Thuau, G. Wantz, L. J. Richter, O. Dautel, G. Hadziioannou, N. Stingelin, Adv. Mater. 2020, 33, 2005723.
M. Moser, A. Savva, K. Thorley, B. D. Paulsen, T. C. Hidalgo, D. Ohayon, H. Chen, A. Giovannitti, A. Marks, N. Gasparini, A. Wadsworth, J. Rivnay, S. Inal, I. McCulloch, Angew. Chem., Int. Ed. 2021, 133, 7856.
S. Inal, G. G. Malliaras, J. Rivnay, Nat. Commun. 2017, 8, 1767.
M. Moser, T. C. Hidalgo, J. Surgailis, J. Gladisch, S. Ghosh, R. Sheelamanthula, Q. Thiburce, A. Giovannitti, A. Salleo, N. Gasparini, A. Wadsworth, I. Zozoulenko, M. Berggren, E. Stavrinidou, S. Inal, I. McCulloch, Adv. Mater. 2020, 32, 2002748.
A. Giovannitti, C. B. Nielsen, D.-T. T. Sbircea, S. Inal, M. Donahue, M. R. Niazi, D. A. Hanifi, A. Amassian, G. G. Malliaras, J. Rivnay, I. Mcculloch, Nat. Commun. 2016, 7, 13066.
A. Giovannitti, I. P. Maria, D. Hanifi, M. J. Donahue, D. Bryant, K. J. Barth, B. E. Makdah, A. Savva, D. Moia, M. Zetek, P. R. F. Barnes, O. G. Reid, S. Inal, G. Rumbles, G. G. Malliaras, J. Nelson, J. Rivnay, I. McCulloch, Chem. Mater. 2018, 30, 2945.
H. Sun, M. Vagin, S. Wang, X. Crispin, R. Forchheimer, M. Berggren, S. Fabiano, Adv. Mater. 2018, 30, 1704916.
C. G. Bischak, L. Q. Flagg, K. Yan, C. Z. Li, D. S. Ginger, ACS Appl. Mater. Interfaces 2019, 11, 28138.
J. Surgailis, A. Savva, V. Druet, B. D. Paulsen, R. Wu, A. Hamidi-Sakr, D. Ohayon, G. Nikiforidis, X. Chen, I. McCulloch, J. Rivnay, S. Inal, Adv. Funct. Mater. 2021, 31, 2010165.
Z. S. Parr, R. Halaksa, P. A. Finn, R. B. Rashid, A. Kovalenko, M. Weiter, J. Rivnay, J. Krajčovič, C. B. Nielsen, ChemPlusChem 2019, 84, 1384.
Z. S. Parr, R. B. Rashid, B. D. Paulsen, B. Poggi, E. Tan, M. Freeley, M. Palma, I. Abrahams, J. Rivnay, C. B. Nielsen, Adv. Electron. Mater. 2020, 6, 2000215.
X. Wu, Q. Liu, A. Surendran, S. E. Bottle, P. Sonar, W. L. Leong, Adv. Electron. Mater. 2021, 7, 2000701.
H. Jia, Z. Huang, P. Li, S. Zhang, Y. Wang, J. Y. Wang, X. Gu, T. Lei, J. Mater. Chem. C 2021, 9, 4927.
G. Krauss, F. Meichsner, A. Hochgesang, J. Mohanraj, S. Salehi, P. Schmode, M. Thelakkat, Adv. Funct. Mater. 2021, 31, 2010048.
Y. Wang, E. Zeglio, H. Liao, J. Xu, F. Liu, Z. Li, I. P. Maria, D. Mawad, A. Herland, I. Mcculloch, W. Yue, Chem. Mater. 2019, 31, 9797.
R. S. Ashraf, A. J. Kronemeijer, D. I. James, H. Sirringhaus, I. McCulloch, Chem. Commun. 2012, 48, 3939.
R. Stalder, J. Mei, K. R. Graham, L. A. Estrada, J. R. Reynolds, Chem. Mater. 2014, 26, 664.
W. Yue, M. Nikolka, M. Xiao, A. Sadhanala, C. B. Nielsen, A. J. P. White, H.-Y. Chen, A. Onwubiko, H. Sirringhaus, I. McCulloch, J. Mater. Chem. C 2016, 4, 9704.
Y. K. Voronina, D. B. Krivolapov, A. V. Bogdanov, V. F. Mironov, I. A. Litvinov, J. Struct. Chem. 2012, 53, 413.
J. Huang, Z. Mao, Z. Chen, D. Gao, C. Wei, W. Zhang, G. Yu, Chem. Mater. 2016, 28, 2209.
J. Liu, G. Ye, H. G. O. Potgieser, M. Koopmans, S. Sami, M. I. Nugraha, D. R. Villalva, H. Sun, J. Dong, X. Yang, X. Qiu, C. Yao, G. Portale, S. Fabiano, T. D. Anthopoulos, D. Baran, R. W. A. Havenith, R. C. Chiechi, L. J. A. Koster, Adv. Mater. 2021, 33, 2006694.
J. Mei, K. R. Graham, R. Stalder, J. R. Reynolds, Org. Lett. 2010, 12, 660.
M. Ashizawa, T. Hasegawa, S. Kawauchi, H. Masunaga, T. Hikima, H. Sato, H. Matsumoto, RSC Adv. 2016, 6, 109434.
D. Yoo, T. Hasegawa, M. Ashizawa, T. Kawamoto, H. Masunaga, T. Hikima, H. Matsumoto, T. Mori, J. Mater. Chem. C 2017, 5, 2509.
G. Kim, A. R. Han, H. R. Lee, J. Lee, J. H. Oh, C. Yang, Chem. Commun. 2014, 50, 2180.
N. M. Randell, C. L. Radford, J. Yang, J. Quinn, D. Hou, Y. Li, T. L. Kelly, Chem. Mater. 2018, 30, 4864.
X. Chen, A. Marks, B. D. Paulsen, R. Wu, R. B. Rashid, H. Chen, M. Alsufyani, J. Rivnay, I. McCulloch, Angew. Chem., Int. Ed. 2021, 60, 9368.
K. Feng, W. Shan, S. Ma, Z. Wu, J. Chen, H. Guo, B. Liu, J. Wang, B. Li, H. Y. Woo, S. Fabiano, W. Huang, X. Guo, Angew. Chem., Int. Ed. 2021, 60, 24198.
X. Chen, Z. Zhang, J. Liu, L. Wang, Polym. Chem. 2017, 8, 5496.
A. C. French, A. L. Thompson, B. G. Davis, Angew. Chem., Int. Ed. 2009, 48, 1248.
R. K. Hallani, B. D. Paulsen, A. J. Petty, R. Sheelamanthula, M. Moser, K. J. Thorley, W. Sohn, R. B. Rashid, A. Savva, S. Moro, J. P. Parker, O. Drury, M. Alsufyani, M. Neophytou, J. Kosco, S. Inal, G. Costantini, J. Rivnay, I. McCulloch, J. Am. Chem. Soc. 2021, 143, 11007.
M. Brinkmann, E. Gonthier, S. Bogen, K. Tremel, S. Ludwigs, M. Hufnagel, M. Sommer, ACS Nano 2012, 6, 10319.
F. Zhang, E. Mohammadi, G. Qu, X. Dai, Y. Diao, Adv. Mater. 2020, 32, 2002823.
N. E. Jackson, B. M. Savoie, K. L. Kohlstedt, M. O. De La Cruz, G. C. Schatz, L. X. Chen, M. A. Ratner, J. Am. Chem. Soc. 2013, 135, 10475.
K. J. Thorley, I. McCulloch, J. Mater. Chem. C 2018, 6, 12413.