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


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.

SUBMITTER: Crespi S 

PROVIDER: S-EPMC9298291 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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

Crespi Stefano S   Simeth Nadja A NA   Di Donato Mariangela M   Doria Sandra S   Stindt Charlotte N CN   Hilbers Michiel F MF   Kiss Ferdinand L FL   Toyoda Ryojun R   Wesseling Sammo S   Buma Wybren Jan WJ   Feringa Ben L BL   Szymański Wiktor W  

Angewandte Chemie (International ed. in English) 20211022 48


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  ...[more]

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