Electrochemical Ring-Opening and -Closing of a Spiropyran

Jorn D Steen, Daniël R Duijnstee, Andy S Sardjan, Jacopo Martinelli, Luuk Kortekaas, Denis Jacquemin*, Wesley R Browne*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

The bistability of molecular switches is an essential characteristic in their use as functional components in molecular-based devices and machines. For photoswitches, light-driven switching between two stable states proceeds via short-lived changes of the bond order in electronically excited states. Here, bistable switching of a ditertbutyl-substituted spiropyran photoswitch is instead demonstrated by oxidation and subsequent reduction in an overall four-state cycle. The spiropyran structure chosen has reduced sensitivity to the effect of secondary electrochemical processes such as H+ production and provides transient access to a decreased thermal Z-E isomerization barrier in the one electron oxidized state, akin to that achieved in the corresponding photochemical path. Thus, we show that the energy needed for switching spiropyrans to the merocyanine form on demand, typically delivered by a photon, can instead be provided electrochemically. This opens up further opportunities for the utilization of spiropyrans in electrically controlled applications and devices.

Original languageEnglish
Pages (from-to)3355–3361
JournalThe Journal of Physical Chemistry. A: Molecules, Spectroscopy, Kinetics, Environment, & General Theory
Volume125
Issue number16
Early online date16-Apr-2021
DOIs
Publication statusPublished - 29-Apr-2021

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