Diarylethene Photoswitches Undergoing 6π Azaelectrocyclic Reaction: Disrotatory Thermal Cycloreversion of the Closed-Ring Isomer

04 August 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Gaining insight into the dynamics of electrocyclic reactions is very important from both fundamental and application perspectives. In this study, we developed novel diarylethene photoswitches that undergo 6 azaelectrocyclic reaction. We found that they exhibit fast thermally reversible type (T-type) photochromism in contrast to the fact that common diarylethenes exhibit photochemically reversible type (P-type) photochromism. The quantum chemical calculations revealed that the fast T-type photochromism originates from the unprecedented disrotatory thermal cycloreversion of the closed-ring isomer. Our results provide useful information not only for the dynamics of the 6 azaelectrocyclic reaction but also for the further development of diarylethene photoswitches utilizing 6 azaelectrocyclic reaction.

Keywords

6π Azaelectrocyclic Reaction
Diarylethene
Woodward-Hoffmann rule

Supplementary materials

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Supporting Information
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Experimental details of syntheses, absorption spectroscopy, theoretical calculations, and the detailed data.
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Video S1
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Associated with Figure 2e.
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Video S2
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Associated with Figure 3a.
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Video S3
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Associated with Figure 3b.
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Video S4
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Molecular geometrical change during the thermal cycloreversion of 1–4.
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