Use of a Multiple Hydride Donor To Achieve an n-Doped Polymer with High Solvent Resistance
Abstract
We report the ability to insolubilize doped semiconducting polymer layers can help enable the fabrication of efficient multilayer solution-processed electronic and optoelectronic devices. Here, we present a promising approach to simultaneously n-dope and largely insolubilize conjugated polymer films using tetrakis[{4-(1,3-dimethyl-2,3-dihydro-1H-benzo[d]imidazol-2-yl)phenoxy}methyl]methane (tetrakis-O-DMBI-H), which consists of four 2,3-dihydro-1H-benzoimidazole (DMBI-H) n-dopant moieties covalently linked to one another. Doping a thiophene-fused benzodifurandione-based oligo(p-phenylenevinylene)-co-thiophene polymer (TBDOPV-T) with tetrakis-O-DMBI-H results in a highly n-doped film with bulk conductivity of 15 S cm–1. Optical absorption spectra provide evidence for film retention of ~93% after immersion in o-dichlorobenzene for 5 min. The optical absorption signature of the charge carriers in the n-doped polymer decreases only slightly more than that of the neutral polymer under these conditions, indicating that the exposure to solvent also results in negligible dedoping of the film. Moreover, thermal treatment studies on a tetrakis-O-DMBI-H-doped TBDOPV-T film in contact with another undoped polymer film indicate immobilization of the molecular dopant in TBDOPV-T. This is attributed to the multiple electrostatic interactions between each dopant tetracation and up to four nearby anionic doped polymer segments.
- Authors:
-
[1];
[2];
[5];
[2];
[1];
[6];
[3];
[5];
[1]
- Georgia Institute of Technology, Atlanta, GA (United States); University of Colorado, Boulder, CO (United States)
- Humboldt University of Berlin (Germany)
- Peking University, Beijing (China)
- SLAC National Accelerator Lab., Menlo Park, CA (United States); Stanford University, CA (United States)
- Humboldt University of Berlin (Germany); Helmholtz-Zentrum Berlin für Materialien und Energie GmbH, Berlin (Germany)
- University of Colorado, Boulder, CO (United States)
- Publication Date:
- Research Org.:
- SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); German Research Foundation (DFG); National Science Foundation (NSF); US Air Force Office of Scientific Research (AFOSR)
- OSTI Identifier:
- 1884813
- Grant/Contract Number:
- AC02-76SF00515; DMR-807797; DMR-22116857; DMR-1729737; FA0550-18-1-0499
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Applied Materials and Interfaces
- Additional Journal Information:
- Journal Volume: 14; Journal Issue: 29; Journal ID: ISSN 1944-8244
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; n-doping; insolubilization; cross-linking; conductivity; hydride; donor
Citation Formats
Saeedifard, Farzaneh, Lungwitz, Dominique, Yu, Zi-Di, Schneider, Sebastian, Mansour, Ahmed E., Opitz, Andreas, Barlow, Stephen, Toney, Michael F., Pei, Jian, Koch, Norbert, and Marder, Seth R. Use of a Multiple Hydride Donor To Achieve an n-Doped Polymer with High Solvent Resistance. United States: N. p., 2022.
Web. doi:10.1021/acsami.2c05724.
Saeedifard, Farzaneh, Lungwitz, Dominique, Yu, Zi-Di, Schneider, Sebastian, Mansour, Ahmed E., Opitz, Andreas, Barlow, Stephen, Toney, Michael F., Pei, Jian, Koch, Norbert, & Marder, Seth R. Use of a Multiple Hydride Donor To Achieve an n-Doped Polymer with High Solvent Resistance. United States. https://doi.org/10.1021/acsami.2c05724
Saeedifard, Farzaneh, Lungwitz, Dominique, Yu, Zi-Di, Schneider, Sebastian, Mansour, Ahmed E., Opitz, Andreas, Barlow, Stephen, Toney, Michael F., Pei, Jian, Koch, Norbert, and Marder, Seth R. Wed .
"Use of a Multiple Hydride Donor To Achieve an n-Doped Polymer with High Solvent Resistance". United States. https://doi.org/10.1021/acsami.2c05724. https://www.osti.gov/servlets/purl/1884813.
@article{osti_1884813,
title = {Use of a Multiple Hydride Donor To Achieve an n-Doped Polymer with High Solvent Resistance},
author = {Saeedifard, Farzaneh and Lungwitz, Dominique and Yu, Zi-Di and Schneider, Sebastian and Mansour, Ahmed E. and Opitz, Andreas and Barlow, Stephen and Toney, Michael F. and Pei, Jian and Koch, Norbert and Marder, Seth R.},
abstractNote = {We report the ability to insolubilize doped semiconducting polymer layers can help enable the fabrication of efficient multilayer solution-processed electronic and optoelectronic devices. Here, we present a promising approach to simultaneously n-dope and largely insolubilize conjugated polymer films using tetrakis[{4-(1,3-dimethyl-2,3-dihydro-1H-benzo[d]imidazol-2-yl)phenoxy}methyl]methane (tetrakis-O-DMBI-H), which consists of four 2,3-dihydro-1H-benzoimidazole (DMBI-H) n-dopant moieties covalently linked to one another. Doping a thiophene-fused benzodifurandione-based oligo(p-phenylenevinylene)-co-thiophene polymer (TBDOPV-T) with tetrakis-O-DMBI-H results in a highly n-doped film with bulk conductivity of 15 S cm–1. Optical absorption spectra provide evidence for film retention of ~93% after immersion in o-dichlorobenzene for 5 min. The optical absorption signature of the charge carriers in the n-doped polymer decreases only slightly more than that of the neutral polymer under these conditions, indicating that the exposure to solvent also results in negligible dedoping of the film. Moreover, thermal treatment studies on a tetrakis-O-DMBI-H-doped TBDOPV-T film in contact with another undoped polymer film indicate immobilization of the molecular dopant in TBDOPV-T. This is attributed to the multiple electrostatic interactions between each dopant tetracation and up to four nearby anionic doped polymer segments.},
doi = {10.1021/acsami.2c05724},
journal = {ACS Applied Materials and Interfaces},
number = 29,
volume = 14,
place = {United States},
year = {Wed Jul 13 00:00:00 EDT 2022},
month = {Wed Jul 13 00:00:00 EDT 2022}
}
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