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

Dmytro Sysoiev | Zendy; Thomas Huhn | Zendy

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

Author(s) -

Dmytro Sysoiev,

Thomas Huhn

Publication year - 2020

Publication title -

photochemical and photobiological sciences

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.699

H-Index - 101

eISSN - 1474-9092

pISSN - 1474-905X

DOI - 10.1039/d0pp00292e

Subject(s) - photochromism , chemistry , knoevenagel condensation , sonogashira coupling , photochemistry , wittig reaction , photoisomerization , organic chemistry , combinatorial chemistry , catalysis , isomerization , palladium

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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