Design and Evaluation of Dansyl-Derived Chemosensors for Disulfide-Cleavage-Triggered Detection: Photophysical, Metal Sensing, and Thermometric Applications

12 November 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

In this work, two new dansyl-derived chemosensors have been designed with the aim of developing a disulfide-cleavage-triggered probe. These stable new ligands, containing a thioether (L1) and a disulfide bridge (L2), have been synthesized and evaluated for their photophysical properties in both solution and solid state. Different fluorescence emission responses have been observed for both compounds due to the self-quenching nature of the disulfide bond compared to L1, with the latter reaching quantum yields close to 50%. Efforts to characterize solute-solvent interactions through Kamlet-Taft studies have revealed a positive solvatofluorochromic response for both compounds. Furthermore, the aggregation-induced emission phenomenon was demonstrated at increasing water fractions. The presence of free thiol groups enhances the complexation ability, making L1 particularly beneficial for sensing Cu²⁺ and Hg²⁺ ions, achieving detection limits as low as 2 µM in the case of mercury. Finally, incorporating L1 into polymer-doped films demonstrated promising results as molecular thermometers, while the response of L2 to sodium dithionite underscores its potential in disulfide-cleavage-triggered applications.

Keywords

Dansyl derivatives
solvatochromism
sodium dithionite
polymers
metal ions

Supplementary materials

Title
Description
Actions
Title
Supplementary Material Design and Evaluation of Dansyl-Derived Chemosensors for Disulfide-Cleavage-Triggered Detection: Photophysical, Metal Sensing, and Thermometric Applications
Description
Index of figures in Supplementary Material: Images of NMR spectra for compound L1 – S1-1 to S1-15. Images of NMR spectra for compound L2 – S2-1 to S2-24. ESI-HRMS spectrum of compound L1 – Figure S3. ESI-HRMS spectrum of compound L2 – Figure S4. Photophysical characterization of L1 in a) chloroform, b) THF, c) ethanol and d) DMSO – Figure S5. Photophysical characterization of L2 in a) chloroform, b) THF, c) ethanol and d) DMSO – Figure S6.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.