ipso-Arylative Ring-Opening Polymerization as a Route to Electron-Deficient Conjugated Polymers
Abstract
ipso–Arylative ring–opening polymerization of 2–bromo–8–aryl–8H–indeno[2,1–b]thiophen–8–ol monomers proceeds to Mn up to 9 kg mol–1 with conversion of the monomer diarylcarbinol groups to pendent conjugated aroylphenyl side chains (2–benzoylphenyl or 2–(4–hexylbenzoyl)phenyl), which influence the optical and electronic properties of the resulting polythiophenes. Poly(3–(2–(4–hexylbenzoyl)phenyl)thiophene) was found to have lower frontier orbital energy levels (HOMO/LUMO=–5.9/–4.0 eV) than poly(3–hexylthiophene) owing to the electron–withdrawing ability of the aryl ketone side chains. The electron mobility (ca. 2×10–3 cm2 V–1 s–1) for poly(3–(2–(4–hexylbenzoyl)phenyl)thiophene) was found to be significantly higher than the hole mobility (ca. 8×10–6 cm2 V–1 s–1), which suggests such polymers are candidates for n–type organic semiconductors. Furthermore, density functional theory calculations suggest that backbone distortion resulting from side–chain steric interactions could be a key factor influencing charge mobilities.
- Authors:
-
[1];
[2];
[2];
[1]
- Stony Brook Univ., Stony Brook, NY (United States)
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Publication Date:
- Research Org.:
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1484440
- Alternate Identifier(s):
- OSTI ID: 1484394
- Report Number(s):
- BNL-209640-2018-JAAM
Journal ID: ISSN 1433-7851
- Grant/Contract Number:
- SC0012704
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 57; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 77 NANOSCIENCE AND NANOTECHNOLOGY; conducting materials; cross-coupling; ipso-arylative polymerization; palladium; ring-opening polymerization
Citation Formats
Shih, Feng -Yang, Choi, Deokkyu, Wu, Qin, Nam, Chang -Yong, and Grubbs, Robert B. ipso-Arylative Ring-Opening Polymerization as a Route to Electron-Deficient Conjugated Polymers. United States: N. p., 2018.
Web. doi:10.1002/anie.201809610.
Shih, Feng -Yang, Choi, Deokkyu, Wu, Qin, Nam, Chang -Yong, & Grubbs, Robert B. ipso-Arylative Ring-Opening Polymerization as a Route to Electron-Deficient Conjugated Polymers. United States. https://doi.org/10.1002/anie.201809610
Shih, Feng -Yang, Choi, Deokkyu, Wu, Qin, Nam, Chang -Yong, and Grubbs, Robert B. Wed .
"ipso-Arylative Ring-Opening Polymerization as a Route to Electron-Deficient Conjugated Polymers". United States. https://doi.org/10.1002/anie.201809610. https://www.osti.gov/servlets/purl/1484440.
@article{osti_1484440,
title = {ipso-Arylative Ring-Opening Polymerization as a Route to Electron-Deficient Conjugated Polymers},
author = {Shih, Feng -Yang and Choi, Deokkyu and Wu, Qin and Nam, Chang -Yong and Grubbs, Robert B.},
abstractNote = {ipso–Arylative ring–opening polymerization of 2–bromo–8–aryl–8H–indeno[2,1–b]thiophen–8–ol monomers proceeds to Mn up to 9 kg mol–1 with conversion of the monomer diarylcarbinol groups to pendent conjugated aroylphenyl side chains (2–benzoylphenyl or 2–(4–hexylbenzoyl)phenyl), which influence the optical and electronic properties of the resulting polythiophenes. Poly(3–(2–(4–hexylbenzoyl)phenyl)thiophene) was found to have lower frontier orbital energy levels (HOMO/LUMO=–5.9/–4.0 eV) than poly(3–hexylthiophene) owing to the electron–withdrawing ability of the aryl ketone side chains. The electron mobility (ca. 2×10–3 cm2 V–1 s–1) for poly(3–(2–(4–hexylbenzoyl)phenyl)thiophene) was found to be significantly higher than the hole mobility (ca. 8×10–6 cm2 V–1 s–1), which suggests such polymers are candidates for n–type organic semiconductors. Furthermore, density functional theory calculations suggest that backbone distortion resulting from side–chain steric interactions could be a key factor influencing charge mobilities.},
doi = {10.1002/anie.201809610},
journal = {Angewandte Chemie (International Edition)},
number = ,
volume = 57,
place = {United States},
year = {2018},
month = {11}
}
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