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

23 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