Synthesis, Structure and Fluorescence Properties of 5,17-Distyryl-25,26,27,28-tetraproproxycalix[4]arenes in the Cone Conformation

Mogens Larsen, Frederik C Krebs, Mikkel Jørgensen, Niels Harrit

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    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 languageEnglish
    JournalJournal of Organic Chemistry
    Volume63
    Pages (from-to)4420-4424
    ISSN0022-3263
    Publication statusPublished - 1998

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