Charge transfer in mixed and segregated stacks of tetrathiafulvalene, tetrathianaphthalene and naphthalene diimide: a structural, spectroscopic and computational study

Chanel F. Leong, Bun Chan, Tianfu Liu, Harrison S. Moore, Idan Hod, Marcello B. Solomon, Pavel M. Usov, Joseph T. Hupp, Omar Farha, Deanna M. D’Alessandro

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Tetrathiafulvalene (TTF) is a highly tunable electron donor that has been widely studied in charge transfer (CT) complexes, including Bechgaard salts which are superconductors at low temperatures. Its close relative, tetrathianaphthalene (TTN) has received considerably less attention than its TTF counterpart but is potentially a versatile electron donor. Three novel CT complexes containing mixed and segregated stack donor-acceptor (D-A) complexes of tetrathiafulvalene (TTF), tetrathianaphthalene (TTN) and naphthalene diimide (NDI) are reported. We demonstrate a facile mechanochemical synthesis of two salts, TTF-DPNI and TTN-DPNI (DPNI = N,N′-di-(4-pyridyl)-1,4,5,8-naphthalenetetracarboxydiimide), which is uncommon for these materials. Despite the detection of a very low partial charge transfer in the three salts using UV-Vis-NIR, Raman and EPR spectroscopies, we elucidated the properties of the TTN core with support from DFT calculations for the first time. We highlight the performance of TTN in a CT complex and demonstrate the importance of a combined approach to the characterisation of CT in organic D-A complexes.

Original languageEnglish
Pages (from-to)10026-10036
Number of pages11
JournalNew Journal of Chemistry
Volume46
Issue number21
DOIs
StatePublished - 25 Apr 2022

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Materials Chemistry

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