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Design principles for photoswitchable fluorescent dyads.

Sili Qiu¹, Andrew T Frawley¹, Kathryn G Leslie¹

¹Chemistry Research Laboratory, Department of Chemistry, University of Oxford Oxford OX1 3TA UK andrew.frawley@chem.ox.ac.uk harry.anderson@chem.ox.ac.uk.

Chemical Science

|October 24, 2025

Summary

This summary is machine-generated.

Designing efficient photoswitchable fluorescent dyes for advanced imaging is challenging. Our study reveals dye-mediated back-isomerization as a key factor, enabling accurate predictions for high-contrast molecular photoswitches.

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Area of Science:

Chemical Physics
Molecular Imaging
Organic Chemistry

Background:

Photoswitchable fluorophores enable precise optical control in advanced imaging techniques.
However, the design principles for efficient photoswitchable fluorescent dyes are not well understood, limiting their application.

Purpose of the Study:

To investigate the design criteria for efficient photoswitchable fluorescent dyes.
To understand the factors influencing fluorescence modulation and quenching in FRET-based dyads.

Main Methods:

Synthesis of four new FRET-based dyads combining photoswitches with fluorescent dyes.
Comparison with three previously reported dyads.
Development of a model to explain observed fluorescence modulation and quenching discrepancies.

Main Results:

Dithienylethene-based dyads showed fluorescence modulation, while diazocine- and fulgimide-based dyads exhibited minimal quenching.
A developed model demonstrated that fluorophore absorption at the photoswitching wavelength can induce dye-mediated back-isomerization.
This back-isomerization was found to reduce the population of the quenching state, explaining the observed minimal quenching.

Conclusions:

The developed model accurately predicts photostationary state distributions for molecular photoswitches and FRET-based dyads.
Key design principles for achieving high-contrast photoswitchable fluorescent dyes were identified.
Understanding dye-mediated back-isomerization is crucial for optimizing photoswitchable dye design.