Abstract
Calix[4]arene- and calix[3]arene-based polyether precursors to polyradicals are synthesized. π-Conjugated carbanions, such as calix[4]arene-based tetraanion and calix[3]arene-based trianion, are prepared and studied using NMR spectroscopy and voltammetry. A 4-fold-symmetric conformer for the tetraanion and two non-interconverting conformers (3-fold- and 2-fold-symmetric) for the trianion are found on the NMR time scale. Oxidation of the tetraanion gives the corresponding calix[4]arene-based S = 2 tetraradical. However, ESR spectroscopy suggests that the predominant product from oxidation of calix[3]arene-based trianion is the corresponding triradical dimer. The related calix[3]arene-based S = 1 diradical is found to be monomeric. Additional characterization of octaradical 18. and pentaradical 25., which were described in a preliminary communication, is presented.
Original language | English (US) |
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Pages (from-to) | 806-816 |
Number of pages | 11 |
Journal | Journal of the American Chemical Society |
Volume | 117 |
Issue number | 2 |
DOIs | |
State | Published - Jan 1995 |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry