Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation

Diego Nava, Younghun Shin, Matteo Massetti, Xuechen Jiao, Till Biskup, Madan S. Jagadeesh, Alberto Calloni, Lamberto Duò, Guglielmo Lanzani, Christopher R. McNeill, Michael Sommer, Mario Caironi

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Organic thermoelectrics are attractive for the fabrication of flexible and cost-effective thermoelectric generators (TEGs) for waste heat recovery, in particular by exploiting large-area printing of polymer conductors. Efficient TEGs require both p- and n-type conductors: so far, the air instability of polymer n-type conductors, which typically lose orders of magnitude in electrical conductivity (σ) even for short exposure time to air, has impeded processing under ambient conditions. Here we tackle this problem in a relevant class of electron transporting, naphthalene-diimide copolymers, by substituting the imide oxygen with sulfur. n-type doping of the thionated copolymer gives rise to a higher σ with respect to the non-thionated one, and most importantly, owing to a reduced energy level of the lowest-unoccupied molecular orbital, σ is substantially stable over 16 h of air exposure. This result highlights the effectiveness of chemical tuning to improve air stability of n-type solution-processable polymer conductors and shows a path toward ambient large-area manufacturing of efficient polymer TEGs.

Original languageEnglish
Pages (from-to)4626-4634
Number of pages9
JournalACS Applied Energy Materials
Volume1
Issue number9
DOIs
Publication statusPublished - 30 Sep 2018

Keywords

  • air stability
  • conjugated polymers
  • n-type doping
  • organic thermoelectrics
  • polymer conductors

Cite this

Nava, Diego ; Shin, Younghun ; Massetti, Matteo ; Jiao, Xuechen ; Biskup, Till ; Jagadeesh, Madan S. ; Calloni, Alberto ; Duò, Lamberto ; Lanzani, Guglielmo ; McNeill, Christopher R. ; Sommer, Michael ; Caironi, Mario. / Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation. In: ACS Applied Energy Materials. 2018 ; Vol. 1, No. 9. pp. 4626-4634.
@article{ddb622ddfd554e6b9bab1f12b5587db4,
title = "Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation",
abstract = "Organic thermoelectrics are attractive for the fabrication of flexible and cost-effective thermoelectric generators (TEGs) for waste heat recovery, in particular by exploiting large-area printing of polymer conductors. Efficient TEGs require both p- and n-type conductors: so far, the air instability of polymer n-type conductors, which typically lose orders of magnitude in electrical conductivity (σ) even for short exposure time to air, has impeded processing under ambient conditions. Here we tackle this problem in a relevant class of electron transporting, naphthalene-diimide copolymers, by substituting the imide oxygen with sulfur. n-type doping of the thionated copolymer gives rise to a higher σ with respect to the non-thionated one, and most importantly, owing to a reduced energy level of the lowest-unoccupied molecular orbital, σ is substantially stable over 16 h of air exposure. This result highlights the effectiveness of chemical tuning to improve air stability of n-type solution-processable polymer conductors and shows a path toward ambient large-area manufacturing of efficient polymer TEGs.",
keywords = "air stability, conjugated polymers, n-type doping, organic thermoelectrics, polymer conductors",
author = "Diego Nava and Younghun Shin and Matteo Massetti and Xuechen Jiao and Till Biskup and Jagadeesh, {Madan S.} and Alberto Calloni and Lamberto Du{\`o} and Guglielmo Lanzani and McNeill, {Christopher R.} and Michael Sommer and Mario Caironi",
year = "2018",
month = "9",
day = "30",
doi = "10.1021/acsaem.8b00777",
language = "English",
volume = "1",
pages = "4626--4634",
journal = "ACS Applied Energy Materials",
issn = "2574-0962",
publisher = "ACS Publications",
number = "9",

}

Nava, D, Shin, Y, Massetti, M, Jiao, X, Biskup, T, Jagadeesh, MS, Calloni, A, Duò, L, Lanzani, G, McNeill, CR, Sommer, M & Caironi, M 2018, 'Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation' ACS Applied Energy Materials, vol. 1, no. 9, pp. 4626-4634. https://doi.org/10.1021/acsaem.8b00777

Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation. / Nava, Diego; Shin, Younghun; Massetti, Matteo; Jiao, Xuechen; Biskup, Till; Jagadeesh, Madan S.; Calloni, Alberto; Duò, Lamberto; Lanzani, Guglielmo; McNeill, Christopher R.; Sommer, Michael; Caironi, Mario.

In: ACS Applied Energy Materials, Vol. 1, No. 9, 30.09.2018, p. 4626-4634.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Drastic Improvement of Air Stability in an n-Type Doped Naphthalene-Diimide Polymer by Thionation

AU - Nava, Diego

AU - Shin, Younghun

AU - Massetti, Matteo

AU - Jiao, Xuechen

AU - Biskup, Till

AU - Jagadeesh, Madan S.

AU - Calloni, Alberto

AU - Duò, Lamberto

AU - Lanzani, Guglielmo

AU - McNeill, Christopher R.

AU - Sommer, Michael

AU - Caironi, Mario

PY - 2018/9/30

Y1 - 2018/9/30

N2 - Organic thermoelectrics are attractive for the fabrication of flexible and cost-effective thermoelectric generators (TEGs) for waste heat recovery, in particular by exploiting large-area printing of polymer conductors. Efficient TEGs require both p- and n-type conductors: so far, the air instability of polymer n-type conductors, which typically lose orders of magnitude in electrical conductivity (σ) even for short exposure time to air, has impeded processing under ambient conditions. Here we tackle this problem in a relevant class of electron transporting, naphthalene-diimide copolymers, by substituting the imide oxygen with sulfur. n-type doping of the thionated copolymer gives rise to a higher σ with respect to the non-thionated one, and most importantly, owing to a reduced energy level of the lowest-unoccupied molecular orbital, σ is substantially stable over 16 h of air exposure. This result highlights the effectiveness of chemical tuning to improve air stability of n-type solution-processable polymer conductors and shows a path toward ambient large-area manufacturing of efficient polymer TEGs.

AB - Organic thermoelectrics are attractive for the fabrication of flexible and cost-effective thermoelectric generators (TEGs) for waste heat recovery, in particular by exploiting large-area printing of polymer conductors. Efficient TEGs require both p- and n-type conductors: so far, the air instability of polymer n-type conductors, which typically lose orders of magnitude in electrical conductivity (σ) even for short exposure time to air, has impeded processing under ambient conditions. Here we tackle this problem in a relevant class of electron transporting, naphthalene-diimide copolymers, by substituting the imide oxygen with sulfur. n-type doping of the thionated copolymer gives rise to a higher σ with respect to the non-thionated one, and most importantly, owing to a reduced energy level of the lowest-unoccupied molecular orbital, σ is substantially stable over 16 h of air exposure. This result highlights the effectiveness of chemical tuning to improve air stability of n-type solution-processable polymer conductors and shows a path toward ambient large-area manufacturing of efficient polymer TEGs.

KW - air stability

KW - conjugated polymers

KW - n-type doping

KW - organic thermoelectrics

KW - polymer conductors

UR - http://www.scopus.com/inward/record.url?scp=85054340554&partnerID=8YFLogxK

U2 - 10.1021/acsaem.8b00777

DO - 10.1021/acsaem.8b00777

M3 - Article

VL - 1

SP - 4626

EP - 4634

JO - ACS Applied Energy Materials

JF - ACS Applied Energy Materials

SN - 2574-0962

IS - 9

ER -