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Thioureas as reporting elements for metal-responsive fluorescent chemosensors
Mireille Vonlanthen1, Nathaniel S Finney
1Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland.
The Journal of Organic Chemistry
|March 9, 2013
Summary
This study demonstrates sulfur-based fluorescent chemosensors for metal ion detection. These novel sulfur chemosensors offer advantages over traditional nitrogen-based sensors, functioning effectively in aqueous solutions.
Area of Science:
- Chemical Sensing
- Materials Science
- Analytical Chemistry
Background:
- Current fluorescent chemosensors predominantly utilize nitrogen coordination, which presents limitations.
- Photoinduced electron transfer (PET) quenching is a common mechanism in existing metal-responsive chemosensors.
- Reliance on nitrogen coordination chemistry is a practical and conceptual constraint in chemosensor development.
Purpose of the Study:
- To establish sulfur as a viable reporting element for metal-responsive fluorescent chemosensors.
- To develop a new class of fluorescent probes based on sulfur's distinct coordination properties.
- To overcome the limitations associated with nitrogen-based chemosensor systems.
Main Methods:
- Utilized thiourea-appended naphthalimides as the core structure for chemosensors.
- Investigated the fluorescence response of these sulfur-containing compounds upon metal ion binding.
- Modified thiourea substituents to control metal affinity and selectivity.
Main Results:
- Demonstrated that metal binding restores quenched fluorescence in thiourea-appended naphthalimides.
- Showcased the ability to tune metal affinity and selectivity through structural modifications.
- Confirmed that these sulfur-based chemosensors operate effectively in aqueous media.
- Observed that the chemosensors are unresponsive to changes in pH, unlike nitrogen-based counterparts.
Conclusions:
- Sulfur is a promising element for developing novel fluorescent chemosensors for metal ions.
- Sulfur-based chemosensors offer distinct advantages, including aqueous compatibility and pH stability.
- This work opens new avenues for creating innovative metal-responsive fluorescent probes.

