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Solvent-Dependent Fluorescence Behavior and Water Detection Sensor Application of Visible Light-Emitting Fluorenone
Jineun Lee1, Heesang Kim1, Toshikazu Sakaguchi2
1Department of Polymer Science & Engineering, Polymeric Nanomaterials Laboratory, Kyungpook National University, 1370 Sankyuk-dong, Buk-ku, Daegu, 702-701, South Korea.
Journal of Fluorescence
|December 12, 2023
Summary
A novel fluorenone derivative exhibits tunable fluorescence colors based on solvent polarity. This D-π-A compound shows fluorescence quenching in alcohols and chloroform due to hydrogen bonding and water presence.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Fluorenone derivatives are known for their optical properties.
- Extended conjugated systems are crucial for tunable electronic and optical behavior.
- Solvatochromism is a key phenomenon in understanding molecular interactions with solvents.
Purpose of the Study:
- To synthesize a fluorenone derivative with an extended conjugated structure.
- To investigate the solvatochromic fluorescence properties of the synthesized compound.
- To explore the quenching mechanisms of fluorescence in specific solvents.
Main Methods:
- Sonogashira coupling reaction for synthesis.
- Spectroscopic analysis of fluorescence in various solvents.
- Correlation of fluorescence changes with solvent polarity and hydrogen bonding.
Main Results:
- A fluorenone derivative with a fluorene-acetylene linkage was successfully synthesized.
- The compound displayed solvatochromic fluorescence, emitting blue, green, and yellow in different solvents.
- Significant fluorescence quenching was observed in alcohols and chloroform, attributed to hydrogen bonding.
- Sensitivity to trace amounts of water, causing fluorescence quenching, was demonstrated.
Conclusions:
- The synthesized fluorenone derivative exhibits tunable fluorescence based on solvent polarity and electronic structure (D-π-A).
- Hydrogen bonding interactions play a critical role in fluorescence quenching mechanisms.
- The compound shows potential as a sensor for water in organic solvents.
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