Helicenes from diarylmaleimides

Harald Bock, Daniel Subervie, Pierre Mathey, Anirban Pradhan, Parantap Sarkar, Pierre Dechambenoit, Elizabeth A. Hillard, Fabien Durola

    Research output: Contribution to journalArticlepeer-review

    32 Citations (Scopus)

    Abstract

    Perkin condensations of arylglyoxylic acids with arylacetic acids, followed by the addition of alkylamine, yield diarylmaleimides in a one-pot procedure. The arylglyoxylic acids are obtained by arene acylation with ClCOCO 2Et and reduced with NaI and hypophosphorous acid to the arylacetic acids. With 2,7-di-tert-butyl-pyren-4-yl or chrysen-6-yl as the aryl, photocyclodehydrogenation of the diarylmaleimides yields substituted helicenes which can be reduced to stable anions. The helicenes combine bathochromically shifted absorption with hypsochromically shifted fluorescence with respect to their precursors.

    Original languageEnglish
    Pages (from-to)1546-1549
    Number of pages4
    JournalOrganic letters
    Volume16
    Issue number6
    DOIs
    Publication statusPublished - 2014 Mar 21

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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