Effect of Backbone Regiochemistry on Conductivity, Charge Density, and Polaron Structure of n-Doped Donor–Acceptor Polymers

Suhao Wang, Daniele Fazzi*, Yuttapoom Puttisong, Mohammad J. Jafari, Zhihua Chen, Thomas Ederth, Jens Wenzel Andreasen, Weimin M. Chen, Antonio Facchetti, Simone Fabiano

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

We investigated the influence of backbone regiochemistry on the conductivity, charge density, and polaron structure in the widely studied n-doped donor–acceptor polymer poly[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenediimide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene) [P(NDI2OD-T2)]. In contrast to classic semicrystalline polymers such as poly(3-hexylthiophene) (P3HT), the regioirregular (RI) structure of the naphthalenediimide (NDI)-bithiophene (T2) backbone does not alter the intramolecular steric demand of the chain versus the regioregular (RR) polymer, yielding RI-P(NDI2OD-T2) with similar energetics and optical features as its RR counterpart. By combining the electrical, UV–vis/infrared, X-ray diffraction, and electron paramagnetic resonance data and density functional theory calculations, we quantitatively characterized the conductivity, aggregation, crystallinity, and charge density, and simulated the polaron structures, molecular vibrations, and spin density distribution of RR-/RI-P(NDI2OD-T2). Importantly, we observed that RI-P(NDI2OD-T2) can be doped to a greater extent compared to its RR counterpart. This finding is remarkable and contrasts benchmark P3HT, allowing us to uniquely study the role of regiochemistry on the charge-transport properties of n-doped donor–acceptor polymers.
Original languageEnglish
JournalChemistry of Materials
Volume31
Issue number9
Pages (from-to)3395-3406
ISSN0897-4756
DOIs
Publication statusPublished - 2019

Cite this

Wang, Suhao ; Fazzi, Daniele ; Puttisong, Yuttapoom ; Jafari, Mohammad J. ; Chen, Zhihua ; Ederth, Thomas ; Andreasen, Jens Wenzel ; Chen, Weimin M. ; Facchetti, Antonio ; Fabiano, Simone. / Effect of Backbone Regiochemistry on Conductivity, Charge Density, and Polaron Structure of n-Doped Donor–Acceptor Polymers. In: Chemistry of Materials. 2019 ; Vol. 31, No. 9. pp. 3395-3406.
@article{3829f161893144e480e12b639bbd1d57,
title = "Effect of Backbone Regiochemistry on Conductivity, Charge Density, and Polaron Structure of n-Doped Donor–Acceptor Polymers",
abstract = "We investigated the influence of backbone regiochemistry on the conductivity, charge density, and polaron structure in the widely studied n-doped donor–acceptor polymer poly[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenediimide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene) [P(NDI2OD-T2)]. In contrast to classic semicrystalline polymers such as poly(3-hexylthiophene) (P3HT), the regioirregular (RI) structure of the naphthalenediimide (NDI)-bithiophene (T2) backbone does not alter the intramolecular steric demand of the chain versus the regioregular (RR) polymer, yielding RI-P(NDI2OD-T2) with similar energetics and optical features as its RR counterpart. By combining the electrical, UV–vis/infrared, X-ray diffraction, and electron paramagnetic resonance data and density functional theory calculations, we quantitatively characterized the conductivity, aggregation, crystallinity, and charge density, and simulated the polaron structures, molecular vibrations, and spin density distribution of RR-/RI-P(NDI2OD-T2). Importantly, we observed that RI-P(NDI2OD-T2) can be doped to a greater extent compared to its RR counterpart. This finding is remarkable and contrasts benchmark P3HT, allowing us to uniquely study the role of regiochemistry on the charge-transport properties of n-doped donor–acceptor polymers.",
author = "Suhao Wang and Daniele Fazzi and Yuttapoom Puttisong and Jafari, {Mohammad J.} and Zhihua Chen and Thomas Ederth and Andreasen, {Jens Wenzel} and Chen, {Weimin M.} and Antonio Facchetti and Simone Fabiano",
year = "2019",
doi = "10.1021/acs.chemmater.9b00558",
language = "English",
volume = "31",
pages = "3395--3406",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "9",

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Wang, S, Fazzi, D, Puttisong, Y, Jafari, MJ, Chen, Z, Ederth, T, Andreasen, JW, Chen, WM, Facchetti, A & Fabiano, S 2019, 'Effect of Backbone Regiochemistry on Conductivity, Charge Density, and Polaron Structure of n-Doped Donor–Acceptor Polymers', Chemistry of Materials, vol. 31, no. 9, pp. 3395-3406. https://doi.org/10.1021/acs.chemmater.9b00558

Effect of Backbone Regiochemistry on Conductivity, Charge Density, and Polaron Structure of n-Doped Donor–Acceptor Polymers. / Wang, Suhao; Fazzi, Daniele; Puttisong, Yuttapoom; Jafari, Mohammad J.; Chen, Zhihua; Ederth, Thomas; Andreasen, Jens Wenzel; Chen, Weimin M.; Facchetti, Antonio; Fabiano, Simone.

In: Chemistry of Materials, Vol. 31, No. 9, 2019, p. 3395-3406.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Effect of Backbone Regiochemistry on Conductivity, Charge Density, and Polaron Structure of n-Doped Donor–Acceptor Polymers

AU - Wang, Suhao

AU - Fazzi, Daniele

AU - Puttisong, Yuttapoom

AU - Jafari, Mohammad J.

AU - Chen, Zhihua

AU - Ederth, Thomas

AU - Andreasen, Jens Wenzel

AU - Chen, Weimin M.

AU - Facchetti, Antonio

AU - Fabiano, Simone

PY - 2019

Y1 - 2019

N2 - We investigated the influence of backbone regiochemistry on the conductivity, charge density, and polaron structure in the widely studied n-doped donor–acceptor polymer poly[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenediimide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene) [P(NDI2OD-T2)]. In contrast to classic semicrystalline polymers such as poly(3-hexylthiophene) (P3HT), the regioirregular (RI) structure of the naphthalenediimide (NDI)-bithiophene (T2) backbone does not alter the intramolecular steric demand of the chain versus the regioregular (RR) polymer, yielding RI-P(NDI2OD-T2) with similar energetics and optical features as its RR counterpart. By combining the electrical, UV–vis/infrared, X-ray diffraction, and electron paramagnetic resonance data and density functional theory calculations, we quantitatively characterized the conductivity, aggregation, crystallinity, and charge density, and simulated the polaron structures, molecular vibrations, and spin density distribution of RR-/RI-P(NDI2OD-T2). Importantly, we observed that RI-P(NDI2OD-T2) can be doped to a greater extent compared to its RR counterpart. This finding is remarkable and contrasts benchmark P3HT, allowing us to uniquely study the role of regiochemistry on the charge-transport properties of n-doped donor–acceptor polymers.

AB - We investigated the influence of backbone regiochemistry on the conductivity, charge density, and polaron structure in the widely studied n-doped donor–acceptor polymer poly[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenediimide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene) [P(NDI2OD-T2)]. In contrast to classic semicrystalline polymers such as poly(3-hexylthiophene) (P3HT), the regioirregular (RI) structure of the naphthalenediimide (NDI)-bithiophene (T2) backbone does not alter the intramolecular steric demand of the chain versus the regioregular (RR) polymer, yielding RI-P(NDI2OD-T2) with similar energetics and optical features as its RR counterpart. By combining the electrical, UV–vis/infrared, X-ray diffraction, and electron paramagnetic resonance data and density functional theory calculations, we quantitatively characterized the conductivity, aggregation, crystallinity, and charge density, and simulated the polaron structures, molecular vibrations, and spin density distribution of RR-/RI-P(NDI2OD-T2). Importantly, we observed that RI-P(NDI2OD-T2) can be doped to a greater extent compared to its RR counterpart. This finding is remarkable and contrasts benchmark P3HT, allowing us to uniquely study the role of regiochemistry on the charge-transport properties of n-doped donor–acceptor polymers.

U2 - 10.1021/acs.chemmater.9b00558

DO - 10.1021/acs.chemmater.9b00558

M3 - Journal article

VL - 31

SP - 3395

EP - 3406

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 9

ER -