The HWE (Horner-Wadsworth-Emmons) reaction performed on the easily obtainable 5,17-diformyl- calixarenes (cone) with arylmethyl phosphorus ylides yielded 5,17-distyryl-25,26,27, 28-tetrapropoxycalixarenes (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 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).
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 1998|