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Issue 10, 2018
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Transforming hemithioindigo from a two-way to a one-way molecular photoswitch by isolation in the gas phase

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Abstract

Hemithioindigo compounds are attractive two-way molecular photoswitches combining stilbene and thioindigo parts connected by a C–C double bond. In solution, these photoswitches have been well studied. This study presents the investigation of a hemithioindigo derivative in the gas phase. Visible absorption spectra, measured by standard (visPD) and helium-tagging visible photodissociation (He-visPD) techniques were used to unravel absorption characteristics at the level of isolated molecules at 3 Kelvin. Comparison between the Z and E isomers shows a quite distinctive behavior upon visible light absorption. The Z isomer readily undergoes ZE conversion in the gas phase, as evidenced by the changes in the helium-tagging infrared photodissociation (He-IRPD) spectra. Surprisingly, visible light excitation of the E isomer does not lead to efficient EZ isomerization unlike in solution. Instead, the ions relax back to their ground state. Influencing the microenvironment of the E isomer by complexation with the highly polar betaine zwitterion resulted in absorption changes, albeit without activating the photoswitching process. Hence, isolation in the gas phase transforms hemithioindigo into a one-way molecular photoswitch. Furthermore, the combination of He-visPD and IRPD spectroscopies proved to be an excellent method for studying photochemical processes such as the double-bond isomerization in the gas phase.

Graphical abstract: Transforming hemithioindigo from a two-way to a one-way molecular photoswitch by isolation in the gas phase

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Supplementary files

Article information


Submitted
05 Jan 2018
Accepted
16 Feb 2018
First published
19 Feb 2018

Phys. Chem. Chem. Phys., 2018,20, 6868-6876
Article type
Paper

Transforming hemithioindigo from a two-way to a one-way molecular photoswitch by isolation in the gas phase

R. Navrátil, S. Wiedbrauk, J. Jašík, H. Dube and J. Roithová, Phys. Chem. Chem. Phys., 2018, 20, 6868
DOI: 10.1039/C8CP00096D

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