Cholesteric aggregation at the quinoidal-to-diradical border enabled stable n-doped conductor

Dafei Yuan, Dazhen Huang, Samara Medina Rivero, Abel Carreras, Cheng Zhang, Ye Zou, Xuechen Jiao, Christopher R. McNeill, Xiaozhang Zhu, Chong an Di, Daoben Zhu, David Casanova, Juan Casado

Research output: Contribution to journalArticleResearchpeer-review

2 Citations (Scopus)

Abstract

Molecular Kekulé diradicals have been demonstrated to show unique optoelectronic properties as a function of their diradical character. A series of thienoquinoidal oligothiophenes from dimer to pentamer and substituted with an odd and even number of pyrrolo-dione groups have been prepared and proven to be n-dopable materials showing outstanding ambient stability and excellent electrical and thermoelectric behavior. Going from dimer to pentamer, a progressive change in the diradical character and aggregation mode is observed, with the tetramer showing an optimal diradical character that allows favorable intermolecular contacts with π−π multi-bonding features, while the presence of the two dione groups promotes a cholesteric-like π−π stacking. Both features synergistically contribute to form a material with exceptional ambient stability for an n-doped system exhibiting high electrical conductivities and thermoelectric performance.

Original languageEnglish
Pages (from-to)964-976
Number of pages13
JournalChem
Volume5
Issue number4
DOIs
Publication statusPublished - 11 Apr 2019

Keywords

  • ambient stability
  • n-type doping
  • organic diradical
  • organic thermoelectrics
  • SDG7: Affordable and clean energy
  • supramolecular packing

Cite this

Yuan, D., Huang, D., Rivero, S. M., Carreras, A., Zhang, C., Zou, Y., ... Casado, J. (2019). Cholesteric aggregation at the quinoidal-to-diradical border enabled stable n-doped conductor. Chem, 5(4), 964-976. https://doi.org/10.1016/j.chempr.2019.02.010
Yuan, Dafei ; Huang, Dazhen ; Rivero, Samara Medina ; Carreras, Abel ; Zhang, Cheng ; Zou, Ye ; Jiao, Xuechen ; McNeill, Christopher R. ; Zhu, Xiaozhang ; Di, Chong an ; Zhu, Daoben ; Casanova, David ; Casado, Juan. / Cholesteric aggregation at the quinoidal-to-diradical border enabled stable n-doped conductor. In: Chem. 2019 ; Vol. 5, No. 4. pp. 964-976.
@article{53c44d6efe9842afa1a30a7447caf4e3,
title = "Cholesteric aggregation at the quinoidal-to-diradical border enabled stable n-doped conductor",
abstract = "Molecular Kekul{\'e} diradicals have been demonstrated to show unique optoelectronic properties as a function of their diradical character. A series of thienoquinoidal oligothiophenes from dimer to pentamer and substituted with an odd and even number of pyrrolo-dione groups have been prepared and proven to be n-dopable materials showing outstanding ambient stability and excellent electrical and thermoelectric behavior. Going from dimer to pentamer, a progressive change in the diradical character and aggregation mode is observed, with the tetramer showing an optimal diradical character that allows favorable intermolecular contacts with π−π multi-bonding features, while the presence of the two dione groups promotes a cholesteric-like π−π stacking. Both features synergistically contribute to form a material with exceptional ambient stability for an n-doped system exhibiting high electrical conductivities and thermoelectric performance.",
keywords = "ambient stability, n-type doping, organic diradical, organic thermoelectrics, SDG7: Affordable and clean energy, supramolecular packing",
author = "Dafei Yuan and Dazhen Huang and Rivero, {Samara Medina} and Abel Carreras and Cheng Zhang and Ye Zou and Xuechen Jiao and McNeill, {Christopher R.} and Xiaozhang Zhu and Di, {Chong an} and Daoben Zhu and David Casanova and Juan Casado",
year = "2019",
month = "4",
day = "11",
doi = "10.1016/j.chempr.2019.02.010",
language = "English",
volume = "5",
pages = "964--976",
journal = "Chem",
issn = "2451-9308",
publisher = "Cell Press",
number = "4",

}

Yuan, D, Huang, D, Rivero, SM, Carreras, A, Zhang, C, Zou, Y, Jiao, X, McNeill, CR, Zhu, X, Di, CA, Zhu, D, Casanova, D & Casado, J 2019, 'Cholesteric aggregation at the quinoidal-to-diradical border enabled stable n-doped conductor', Chem, vol. 5, no. 4, pp. 964-976. https://doi.org/10.1016/j.chempr.2019.02.010

Cholesteric aggregation at the quinoidal-to-diradical border enabled stable n-doped conductor. / Yuan, Dafei; Huang, Dazhen; Rivero, Samara Medina; Carreras, Abel; Zhang, Cheng; Zou, Ye; Jiao, Xuechen; McNeill, Christopher R.; Zhu, Xiaozhang; Di, Chong an; Zhu, Daoben; Casanova, David; Casado, Juan.

In: Chem, Vol. 5, No. 4, 11.04.2019, p. 964-976.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Cholesteric aggregation at the quinoidal-to-diradical border enabled stable n-doped conductor

AU - Yuan, Dafei

AU - Huang, Dazhen

AU - Rivero, Samara Medina

AU - Carreras, Abel

AU - Zhang, Cheng

AU - Zou, Ye

AU - Jiao, Xuechen

AU - McNeill, Christopher R.

AU - Zhu, Xiaozhang

AU - Di, Chong an

AU - Zhu, Daoben

AU - Casanova, David

AU - Casado, Juan

PY - 2019/4/11

Y1 - 2019/4/11

N2 - Molecular Kekulé diradicals have been demonstrated to show unique optoelectronic properties as a function of their diradical character. A series of thienoquinoidal oligothiophenes from dimer to pentamer and substituted with an odd and even number of pyrrolo-dione groups have been prepared and proven to be n-dopable materials showing outstanding ambient stability and excellent electrical and thermoelectric behavior. Going from dimer to pentamer, a progressive change in the diradical character and aggregation mode is observed, with the tetramer showing an optimal diradical character that allows favorable intermolecular contacts with π−π multi-bonding features, while the presence of the two dione groups promotes a cholesteric-like π−π stacking. Both features synergistically contribute to form a material with exceptional ambient stability for an n-doped system exhibiting high electrical conductivities and thermoelectric performance.

AB - Molecular Kekulé diradicals have been demonstrated to show unique optoelectronic properties as a function of their diradical character. A series of thienoquinoidal oligothiophenes from dimer to pentamer and substituted with an odd and even number of pyrrolo-dione groups have been prepared and proven to be n-dopable materials showing outstanding ambient stability and excellent electrical and thermoelectric behavior. Going from dimer to pentamer, a progressive change in the diradical character and aggregation mode is observed, with the tetramer showing an optimal diradical character that allows favorable intermolecular contacts with π−π multi-bonding features, while the presence of the two dione groups promotes a cholesteric-like π−π stacking. Both features synergistically contribute to form a material with exceptional ambient stability for an n-doped system exhibiting high electrical conductivities and thermoelectric performance.

KW - ambient stability

KW - n-type doping

KW - organic diradical

KW - organic thermoelectrics

KW - SDG7: Affordable and clean energy

KW - supramolecular packing

UR - http://www.scopus.com/inward/record.url?scp=85062703642&partnerID=8YFLogxK

U2 - 10.1016/j.chempr.2019.02.010

DO - 10.1016/j.chempr.2019.02.010

M3 - Article

AN - SCOPUS:85062703642

VL - 5

SP - 964

EP - 976

JO - Chem

JF - Chem

SN - 2451-9308

IS - 4

ER -