Research output: Contribution to journal › Article › peer-review
Journal | Tetrahedron |
---|---|
Date | Accepted/In press - 9 Jan 2017 |
Date | E-pub ahead of print - 12 Jan 2017 |
Date | Published (current) - 2 Mar 2017 |
Issue number | 9 |
Volume | 73 |
Number of pages | 8 |
Pages (from-to) | 1230-1237 |
Early online date | 12/01/17 |
Original language | English |
Direct mercuration and subsequent transformation of organomercurial intermediates into the corresponding nitroso derivatives enabled the construction of calix[4]arenes bearing azo moieties at the meta position (to the alkoxy groups). These compounds, representing a unique substitution pattern in calixarene chemistry, showed very unusual dynamic behaviour in solution. Temperature dependent1H NMR spectra confirmed that the introduction of two bulky moieties (or even just one) into the meta position of calix[4]arene led to the rigidification of the molecule as demonstrated by complete arrest of the typical pinched cone – pinched cone interconversion in solution. The rigidified molecules can be used as ligands capable of cation−π interactions with N-methylpyridinium salts.
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