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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.
Supplementary materials
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.
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