Phenylimino Indolinone: A Green-Light-Responsive T-Type Photoswitch Exhibiting Negative Photochromism

Stefano Crespi*, Nadja A. Simeth, Mariangela Di Donato, Sandra Doria, Charlotte N. Stindt, Michiel F. Hilbers, Ferdinand L. Kiss, Ryojun Toyoda, Sammo Wesseling, Wybren Jan Buma, Ben L. Feringa*, Wiktor Szymański*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

29 Citations (Scopus)
147 Downloads (Pure)

Abstract

Imines are photoaddressable motifs useful in the development of new generations of molecular switches, but their operation with low-energy photons and control over isomer stability remain challenging. Based on a computational design, we developed phenylimino indolinone (PIO), a green-light-addressable T-type photoswitch showing negative photochromism. The isomerization behavior of this photoactuator of the iminothioindoxyl (ITI) class was studied using time-resolved spectroscopies on time scales from femtoseconds to the steady state and by quantum-chemical analyses. The understanding of the isomerization properties and substituent effects governing these photoswitches opens new avenues for the development of novel T-type visible-light-addressable photoactuators based on C=N bonds.

Original languageEnglish
Pages (from-to)25290-25295
Number of pages6
JournalAngewandte Chemie - International Edition
Volume60
Issue number48
Early online date5-Oct-2021
DOIs
Publication statusPublished - 22-Nov-2021

Keywords

  • computational chemistry
  • isomerization
  • molecular dynamics
  • photochromism
  • time-resolved spectroscopy

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