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Basic enemies of photochromism: irreversible transformation of fluorinated diarylethenes to polyenic enamines and enols

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Abstract

Non-photochemical degradation of perfluorinated photochromic diarylethenes (DAE) under Knoevenagel, Sonogashira or Wittig conditions was discovered. This base promoted formation of strongly colored non-photochromic byproducts has an impact in the field of molecular electronics due to the basic conditions often employed during deacylation and desilylation of the protected thiol anchoring groups of functionalized DAE. The products were identified as seven-membered ring systems of the bicyclo[5.3.0]deca-1,7-diene type. Their formation was rationalized by a tentative two-step reaction mechanism.

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Author notes

  1. Dmytro Sysoiev

    Present address: Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences Flemingovo nam. 2, 16610, Prague, Czech Republic

Authors and Affiliations

  1. Fachbereich Chemie, Universität Konstanz, 78464, Konstanz, Germany

    Dmytro Sysoiev & Thomas Huhn

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  1. Dmytro Sysoiev
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  2. Thomas Huhn
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Correspondence to Thomas Huhn.

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Sysoiev, D., Huhn, T. Basic enemies of photochromism: irreversible transformation of fluorinated diarylethenes to polyenic enamines and enols. Photochem Photobiol Sci 19, 1511–1516 (2020). https://doi.org/10.1039/d0pp00292e

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