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

Abstract

A 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 impact in the field of molecular electronics due to basic conditions often employed during deacylation and desilylation of protected thiol anchoring groups of functionalized DAE. Products were identified as seven-membered ring systems of the bicyclo[5.3.0]deca-1,7-diene type. Their formation is rationalized by a tentative two-step reaction mechanism.

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Supplementary files

Article information


Submitted
28 Aug 2020
Accepted
14 Oct 2020
First published
15 Oct 2020

Photochem. Photobiol. Sci., 2020, Accepted Manuscript
Article type
Communication

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

T. Huhn and D. Sysoiev, Photochem. Photobiol. Sci., 2020, Accepted Manuscript , DOI: 10.1039/D0PP00292E

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