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 language | English (US) |
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Article number | C07705SS |
Pages (from-to) | 3437-3445 |
Number of pages | 9 |
Journal | Synthesis |
Issue number | 19 |
DOIs | |
State | Published - Dec 1 2005 |
Keywords
- Molecular recognition
- Redox reactions
- Self-assembly
- Spectroelectrochemistry
- Templation
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry