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Title: ipso-Arylative Ring-Opening Polymerization as a Route to Electron-Deficient Conjugated Polymers

ipso–Arylative ring–opening polymerization of 2–bromo–8–aryl–8 H–indeno[2,1–b]thiophen–8–ol monomers proceeds to M n 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 cm 2 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 cm 2 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] ; ORCiD logo [1] ; ORCiD logo [2] ; ORCiD logo [2] ; ORCiD logo [1]
  1. Stony Brook Univ., Stony Brook, NY (United States)
  2. Brookhaven National Lab. (BNL), Upton, NY (United States)
Publication Date:
Report Number(s):
BNL-209640-2018-JAAM
Journal ID: ISSN 1433-7851
Grant/Contract Number:
SC0012704; Scientific Data & Computing Center
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
Research Org:
Brookhaven National Laboratory (BNL), Upton, NY (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
Language:
English
Subject:
77 NANOSCIENCE AND NANOTECHNOLOGY; conducting materials; cross-coupling; ipso-arylative polymerization; palladium; ring-opening polymerization
OSTI Identifier:
1484440
Alternate Identifier(s):
OSTI ID: 1484394

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., 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. doi:10.1002/anie.201809610.
Shih, Feng -Yang, Choi, Deokkyu, Wu, Qin, Nam, Chang -Yong, and Grubbs, Robert B. 2018. "ipso-Arylative Ring-Opening Polymerization as a Route to Electron-Deficient Conjugated Polymers". United States. doi:10.1002/anie.201809610.
@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}
}

Works referenced in this record:

Living ring-opening metathesis polymerization
journal, January 2007