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Updated: May 4, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Cyclization-induced turn-on fluorescence system applicable to dicarboxylate sensing.
Takao Noguchi1, Bappaditya Roy, Daisuke Yoshihara
1Institute for Advanced Study, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395 (Japan); Nanotechnology Laboratory, Institute of Systems, Information Technologies and Nanotechnologies (ISIT), 4-1 Kyudai-Shinmachi, Nishi-ku, Fukuoka 819-0388 (Japan).
A new fluorescence (FL) chemosensor shows nonlinear turn-on FL switching. This occurs through cooperative binding of L-tartarate, enabling selective detection of dicarboxylates for potential metabolic disorder screening.
Area of Science:
- Chemical sensing
- Fluorescence spectroscopy
- Biomarker detection
Background:
- Fluorescence (FL) chemosensors are crucial for detecting specific analytes.
- Nonlinear FL switching presents opportunities for enhanced sensitivity and selectivity.
- Metabolic disorders often involve altered levels of specific organic acids.
Purpose of the Study:
- To develop a novel tetraphenylethene-based fluorescence (FL) chemosensor.
- To investigate its nonlinear turn-on FL switching mechanism.
- To assess its potential for selective dicarboxylate detection and metabolic disorder screening.
Main Methods:
- Synthesis of a novel tetraphenylethene-based chemosensor.
- Investigation of fluorescence response upon analyte binding.
- Analysis of binding modes and cooperative effects.
- Evaluation of selectivity for dicarboxylates versus monocarboxylates.
Main Results:
- The chemosensor demonstrated nonlinear turn-on FL switching.
- Cooperative binding of L-tartarate was identified as the key mechanism.
- Formation of cyclic substructures upon binding led to FL increase.
- Selective detection of dicarboxylates over monocarboxylates was achieved.
Conclusions:
- The developed chemosensor exhibits unique nonlinear FL switching behavior.
- Cooperative binding and cyclic substructure formation are responsible for the observed FL enhancement.
- The sensor's selectivity for dicarboxylates holds promise for preliminary metabolic disorder screening.

