Template-directed syntheses of configurable and reconfigurable molecular switches

Yi Liu, Sourav Saha, Scott A. Vignon, Amar H. Flood, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Two self-complexing compounds based on donor-acceptor interactions, one comprised of a π-electron-deficient cyclobis(paraquat-p-phenylene) (CBPQT4+) ring attached to a side-arm component containing π-electron-rich tetrathiafulvalene (TTF) and 1,5-dioxynaphthalene (DNP) units, and the other comprised of a CBPQT4+ ring carrying two side-arms, one containing a TTF unit and the other a DNP unit have been synthesized. 1H NMR spectroscopy and UV/Vis spectroelectrochemistry have revealed that, while the latter compound behaves as a reconfigurable redox-active molecular switch involving only the side-arm containing the TTF unit in a self-complexing role with the CBPQT4+ ring (the side-arm containing the DNP unit is essentially a 'spectator'), the former compound behaves as a molecular switch that is reversible and reconfigurable when its starting self-complexing conformation is retained, but becomes only configurable and irreversible when the self-complexing conformation is partially transformed into 'uncomplexed' conformation on oxidation of the TTF unit.

Original languageEnglish (US)
Article numberC07705SS
Pages (from-to)3437-3445
Number of pages9
JournalSynthesis
Issue number19
DOIs
StatePublished - Dec 1 2005

Keywords

  • Molecular recognition
  • Redox reactions
  • Self-assembly
  • Spectroelectrochemistry
  • Templation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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