Triphenylamine/Tetracyanobutadiene-Based π-Conjugated Push–Pull Molecules End-Capped with Arene Platforms: Synthesis, Photophysics, and Photovoltaic Response

Pablo Simon Marques, Jose Maria Andres Castan, Benedito A. L. Raul, Giacomo Londi, Ivan Ramirez, Maxim S. Pshenichnikov*, David Beljonne*, Karsten Walzer, Martin Blais, Magali Allain, Clement Cabanetos, Philippe Blanchard*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)

Abstract

π-Conjugated push–pull molecules based on triphenylamine and 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) have been functionalized with different terminal arene units. In solution, these highly TCBD-twisted systems showed a strong internal charge transfer band in the visible spectrum and no detectable photoluminescence (PL). Photophysical and theoretical investigations revealed very short singlet excited state deactivation time of ≈10 ps resulting from significant conformational changes of the TCBD-arene moiety upon photoexcitation, opening a pathway for non-radiative decay. The PL was recovered in vacuum-processed films or when the molecules were dispersed in a PMMA matrix leading to a significant increase of the excited state deactivation time. As shown by cyclic voltammetry, these molecules can act as electron donors compared to C 60. Hence, vacuum-processed planar heterojunction organic solar cells were fabricated leading to a maximum power conversion efficiency of ca. 1.9 % which decreases with the increase of the arene size.

Original languageEnglish
Pages (from-to)16422-16433
Number of pages12
JournalChemistry
Volume26
Issue number69
Early online date9-Nov-2020
DOIs
Publication statusPublished - 9-Dec-2020

Keywords

  • computational chemistry
  • donor&#8211
  • acceptor systems
  • organic solar cells
  • photophysics
  • tetracyanobutadiene
  • ORGANIC SOLAR-CELLS
  • CHARGE-TRANSFER INTERACTIONS
  • DONOR-ACCEPTOR MOLECULES
  • LIGHT-EMITTING-DIODES
  • HIGHLY EFFICIENT
  • OPTOELECTRONIC PROPERTIES
  • ELECTRONIC-PROPERTIES
  • EXCITON DIFFUSION
  • TRIPHENYLAMINE
  • CHROMOPHORES
  • donor–acceptor systems

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