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Updated: Jun 12, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Diclofenac Detection via Inner-Filter Effect Using Pyridine-Modified Triphenylene.

Matti Haukka¹, Navdeep Kajal², Amar Raj¹

¹Department of Chemistry, University of Jyväskylä, P. O. Box 35, Jyväskylä, FI-40014, Finland.

|June 11, 2025

Summary

New triphenylene derivatives act as selective chemosensors for detecting diclofenac, a nonsteroidal anti-inflammatory drug. This cost-effective method offers high sensitivity and works even in natural water samples.

Keywords:

diclofenac fluorescence quenching hexa‐pyridine triphenylene inner‐filter effects sensors

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Area of Science:

Organic Chemistry
Analytical Chemistry
Materials Science

Background:

Triphenylene derivatives are explored for their unique photophysical properties.
Development of selective chemosensors for pharmaceutical compounds is crucial.
Diclofenac detection is important for environmental and health monitoring.

Purpose of the Study:

To synthesize novel triphenylene derivatives, 3PY and 4PY.
To evaluate their efficacy as chemosensors for diclofenac detection.
To investigate the sensing mechanism and assess practical applicability.

Main Methods:

Suzuki-Miyaura coupling for synthesis of triphenylene derivatives.
Spectroscopic analysis (UV-vis absorption and fluorescence) for sensing.
Testing selectivity against various drugs and hormones.
Determination of limit of detection (LOD) and recovery in real samples.

Main Results:

Successful synthesis of 3PY and 4PY.
High selectivity of the derivatives for diclofenac over other NSAIDs and hormones.
Fluorescence quenching mechanism identified as inner filter effect (IFE).
Achieved a low LOD of 1.18 µM for diclofenac detection.
Demonstrated reliable performance in lake water samples.

Conclusions:

Triphenylene derivatives 3PY and 4PY are effective and selective chemosensors for diclofenac.
The IFE mechanism provides a basis for sensitive fluorescence quenching.
The developed method is simple, cost-effective, and applicable to real-world samples.