Abstract
By applying electrophilic aromatic mercuration of calix[4]arene the introduction of substituted hydroxymethyl groups at the meta position of the basic skeleton has been achieved. Subsequent intramolecular Friedel-Crafts alkylation led to a novel type of bridged calix[4]arenes with additional symmetrically substituted methylene bridges connecting to the neighbouring aromatic units. Additionally, this new efficient synthetic pathway was also used for the preparation of a double bridged analogue. These compounds with rigidified cavities can complex cations and neutral compounds using CH-π and/or cation-π interactions as demonstrated by 1H NMR titration experiments.
Original language | English |
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Pages (from-to) | 14738-14745 |
Number of pages | 8 |
Journal | NEW JOURNAL OF CHEMISTRY |
Volume | 41 |
Issue number | 23 |
DOIs | |
Publication status | Published - 2 Nov 2017 |