Stable High‐Conductivity Ethylenedioxythiophene Polymers via Borane‐Adduct Doping
Abstract
Abstract Efficient doping of polymer semiconductors is required for high conductivity and efficient thermoelectric performance. Lewis acids, e.g., B(C 6 F 5 ) 3 , have been widely employed as dopants, but the mechanism is not fully understood. 1:1 “Wheland type” or zwitterionic complexes of B(C 6 F 5 ) 3 are created with small conjugated molecules 3,6‐bis(5‐(7‐(5‐methylthiophen‐2‐yl)‐2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)thiophen‐2‐yl)‐2,5‐dioctyl‐2,5‐dihydropyrrolo[3,4‐c]pyrrole‐1,4‐dione [oligo_DPP(EDOT) 2 ] and 3,6‐bis(5''‐methyl‐[2,2':5',2''‐terthiophen]‐5‐yl)‐2,5‐dioctyl‐2,5‐dihydropyrrolo[3,4‐c]pyrrole‐1,4‐dione [oligo_DPP(Th) 2 ]. Using a wide variety of experimental and computational approaches, the doping ability of these Wheland Complexes with B(C 6 F 5 ) 3 are characterized for five novel diketopyrrolopyrrole‐ethylenedioxythiophene (DPP‐EDOT)‐based conjugated polymers. The electrical properties are a strong function of the specific conjugated molecule constituting the adduct, rather than acidic protons generated via hydrolysis of B(C 6 F 5 ) 3 , serving as the oxidant. It is highly probable that certain repeat units/segments form adduct structures in p ‐type conjugated polymers which act as intermediates for conjugated polymer doping. Electronic and optical properties are consistent with the increase in hole‐donating ability of polymers with their cumulative donor strengths. The doped film of polymer (DPP(EDOT) 2 ‐(EDOT) 2 ) exhibits exceptionally good thermal and air‐storage stability. The highest conductivities, ≈300 and ≈200 S cm −1 ,more »
- Authors:
-
[1]
- Department of Materials Science and Engineering Johns Hopkins University 3400 N Charles Street Baltimore MD 20218 USA
- Department of Chemical and Biomolecular Engineering Johns Hopkins University 3400 N Charles Street Baltimore MD 20218 USA
- Department of Mechanical Engineering Johns Hopkins University 3400 N Charles Street Baltimore MD 20218 USA
- Department of Electrical and Computer Engineering Johns Hopkins University 3400 N Charles Street Baltimore MD 20218 USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1995886
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Advanced Functional Materials
- Additional Journal Information:
- Journal Name: Advanced Functional Materials Journal Volume: 32 Journal Issue: 51; Journal ID: ISSN 1616-301X
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Mukhopadhyaya, Tushita, Lee, Taein D., Ganley, Connor, Tanwar, Swati, Raj, Piyush, Li, Lulin, Song, Yunjia, Clancy, Paulette, Barman, Ishan, Thon, Susanna, and Katz, Howard E. Stable High‐Conductivity Ethylenedioxythiophene Polymers via Borane‐Adduct Doping. Germany: N. p., 2022.
Web. doi:10.1002/adfm.202208541.
Mukhopadhyaya, Tushita, Lee, Taein D., Ganley, Connor, Tanwar, Swati, Raj, Piyush, Li, Lulin, Song, Yunjia, Clancy, Paulette, Barman, Ishan, Thon, Susanna, & Katz, Howard E. Stable High‐Conductivity Ethylenedioxythiophene Polymers via Borane‐Adduct Doping. Germany. https://doi.org/10.1002/adfm.202208541
Mukhopadhyaya, Tushita, Lee, Taein D., Ganley, Connor, Tanwar, Swati, Raj, Piyush, Li, Lulin, Song, Yunjia, Clancy, Paulette, Barman, Ishan, Thon, Susanna, and Katz, Howard E. Thu .
"Stable High‐Conductivity Ethylenedioxythiophene Polymers via Borane‐Adduct Doping". Germany. https://doi.org/10.1002/adfm.202208541.
@article{osti_1995886,
title = {Stable High‐Conductivity Ethylenedioxythiophene Polymers via Borane‐Adduct Doping},
author = {Mukhopadhyaya, Tushita and Lee, Taein D. and Ganley, Connor and Tanwar, Swati and Raj, Piyush and Li, Lulin and Song, Yunjia and Clancy, Paulette and Barman, Ishan and Thon, Susanna and Katz, Howard E.},
abstractNote = {Abstract Efficient doping of polymer semiconductors is required for high conductivity and efficient thermoelectric performance. Lewis acids, e.g., B(C 6 F 5 ) 3 , have been widely employed as dopants, but the mechanism is not fully understood. 1:1 “Wheland type” or zwitterionic complexes of B(C 6 F 5 ) 3 are created with small conjugated molecules 3,6‐bis(5‐(7‐(5‐methylthiophen‐2‐yl)‐2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)thiophen‐2‐yl)‐2,5‐dioctyl‐2,5‐dihydropyrrolo[3,4‐c]pyrrole‐1,4‐dione [oligo_DPP(EDOT) 2 ] and 3,6‐bis(5''‐methyl‐[2,2':5',2''‐terthiophen]‐5‐yl)‐2,5‐dioctyl‐2,5‐dihydropyrrolo[3,4‐c]pyrrole‐1,4‐dione [oligo_DPP(Th) 2 ]. Using a wide variety of experimental and computational approaches, the doping ability of these Wheland Complexes with B(C 6 F 5 ) 3 are characterized for five novel diketopyrrolopyrrole‐ethylenedioxythiophene (DPP‐EDOT)‐based conjugated polymers. The electrical properties are a strong function of the specific conjugated molecule constituting the adduct, rather than acidic protons generated via hydrolysis of B(C 6 F 5 ) 3 , serving as the oxidant. It is highly probable that certain repeat units/segments form adduct structures in p ‐type conjugated polymers which act as intermediates for conjugated polymer doping. Electronic and optical properties are consistent with the increase in hole‐donating ability of polymers with their cumulative donor strengths. The doped film of polymer (DPP(EDOT) 2 ‐(EDOT) 2 ) exhibits exceptionally good thermal and air‐storage stability. The highest conductivities, ≈300 and ≈200 S cm −1 , are achieved for DPP(EDOT) 2 ‐(EDOT) 2 doped with B(C 6 F 5 ) 3 and its Wheland complexes.},
doi = {10.1002/adfm.202208541},
journal = {Advanced Functional Materials},
number = 51,
volume = 32,
place = {Germany},
year = {Thu Oct 06 00:00:00 EDT 2022},
month = {Thu Oct 06 00:00:00 EDT 2022}
}
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