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

Shih, Feng -Yang; Choi, Deokkyu; Wu, Qin; Nam, Chang -Yong; Grubbs, Robert B.

doi:10.1002/anie.201809610

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

Journal Article · 14 November 2018 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.201809610 · OSTI ID:1484440

Shih, Feng -Yang ^[1];

^[1];

^[2];

^[1]

Stony Brook Univ., Stony Brook, NY (United States)
Brookhaven National Lab. (BNL), Upton, NY (United States)

Abstract 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. Density functional theory calculations suggest that backbone distortion resulting from side‐chain steric interactions could be a key factor influencing charge mobilities.

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Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0012704

OSTI ID:: 1484440

Alternate ID(s):: OSTI ID: 1484394

Report Number(s):: BNL-209640-2018-JAAM

Journal Information:: Angewandte Chemie (International Edition), Vol. 57; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 3 works

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