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Benzo-Crown-Ether Functionalized O-BODIPY Probes for Cations - A Selective Fluorescent Probe for Ba2.
Tobias Sprenger1, Thomas Schwarze2, Hans-Jürgen Holdt2
1Medizinische Fakultät, HMU Potsdam, Olympischer Weg 1, Potsdam, 14471, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 6, 2024
Summary
New methoxy-substituted BODIPY (O-BODIPY) fluorescent probes demonstrate enhanced aqueous solubility and fluorescence. These probes show sensitive and selective cation detection, particularly for barium ions (Ba2+), via fluorescence enhancement.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Analytical Chemistry
Background:
- Boron-dipyrromethene (BODIPY) dyes are widely used as fluorescent probes.
- Crown ethers are known for their ability to bind specific metal cations.
- Developing water-soluble fluorescent probes with high sensitivity and selectivity remains a challenge.
Purpose of the Study:
- To synthesize and characterize novel 4,4'-methoxy-substituted BODIPY (O-BODIPY) fluorescent probes functionalized with varying sizes of benzo-crown ethers.
- To investigate the photophysical properties and cation-sensing capabilities of these O-BODIPYs in aqueous media.
- To compare their performance with previously reported fluoro-substituted BODIPY (F-BODIPY) analogues.
Main Methods:
- Synthesis of O-BODIPY probes 3, 4, and 5, incorporating benzo-15-crown-5, benzo-18-crown-6, and benzo-21-crown-7, respectively.
- Spectroscopic analysis including fluorescence quantum yield measurements.
- Fluorometric titration studies in aqueous solutions with various cations to assess fluorescence enhancement and selectivity.
Main Results:
- O-BODIPYs 3, 4, and 5 exhibit improved aqueous solubility and higher fluorescence quantum yields compared to their F-BODIPY counterparts.
- Cation binding induces fluorescence enhancement (FE) in O-BODIPYs in aqueous solutions.
- While O-BODIPYs show lower cation-induced FEs than F-BODIPYs, their reduced fluorescence quenching allows for sensitive and selective "ON" switching detection.
- Probe 5, featuring benzo-21-crown-7, demonstrates good fluorometric selectivity and sensitivity for barium ions (Ba2+).
Conclusions:
- Methoxy-substituted BODIPY probes with benzo-crown ethers offer a promising platform for aqueous-based fluorescent sensing.
- The O-BODIPY structure facilitates effective "ON" switching detection of cations due to less efficient photoinduced electron transfer.
- The benzo-21-crown-7 functionalized probe 5 is particularly suitable for selective and sensitive detection of Ba2+ in aqueous environments.
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