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Issue 25, 2020
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Selective thiolation and photoswitching mechanism of Cy5 studied by time-dependent density functional theory

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Abstract

Cy5 is one of the most widely used organic dyes with a photoswitching property. It can be reversibly photoconverted to the dark state through thiolation with primary thiols. Although photoswitching of Cy5 has been widely used in super-resolution nanoscopy, its thiolation mechanism remains unclear. We carried out time-dependent density functional theory calculations to investigate the excited state dynamics of Cy5 and observed its site-selective thiolation on both the ground and excited states. Scanning the excited state potential energy surfaces by rotating individual C–C bonds revealed structural similarity between the twisted form of Cy5 and the Cy5 subunit in the thiolated Cy5, which suggests that the dark state formation is strongly associated with the torsional motion on the excited state.

Graphical abstract: Selective thiolation and photoswitching mechanism of Cy5 studied by time-dependent density functional theory

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Supplementary files

Article information


Submitted
03 Jan 2020
Accepted
28 May 2020
First published
01 Jun 2020

Phys. Chem. Chem. Phys., 2020,22, 14125-14129
Article type
Paper

Selective thiolation and photoswitching mechanism of Cy5 studied by time-dependent density functional theory

E. Lim, J. Kwon, J. Park, J. Heo and S. K. Kim, Phys. Chem. Chem. Phys., 2020, 22, 14125
DOI: 10.1039/D0CP00026D

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