Abstract
The HWE (Horner-Wadsworth-Emmons) reaction performed on the easily
obtainable 5,17-diformyl- calix[4]arenes (cone) with arylmethyl
phosphorus ylides yielded 5,17-distyryl-25,26,27,
28-tetrapropoxycalix[4]arenes (cone) in high yield and purely in
the E/E configuration. Compounds 2-5 were prepared this way
containing bromine. Subsequent bromine-lithium exchange and
reaction with trimethoxyborane yielded the boryl- substituted
5,17-distyrylcalix[4] arenes 6-7a. The structures of 3, 5, and 7a
were determined by X-ray diffraction. The photophysical properties
of 2 were established by absorption and fluorescence spectroscopy
and compared to the monomeric fluorophore,
3,5-dimethyl-4-propoxy-(E)-stilbene (10).
| Original language | English |
|---|---|
| Journal | Journal of Organic Chemistry |
| Volume | 63 |
| Pages (from-to) | 4420-4424 |
| ISSN | 0022-3263 |
| Publication status | Published - 1998 |