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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Patterning of pH sensitive fluorescent bipyridazine derivatives
Jaekwon Do1, Yuna Kim, André-Jean Attias
1Department of Chemical and Biomolecular Engineering, Yonsei University, 134 Sinchon-Dong, Seodaemum-Gu, 120-749 Seoul, South Korea.
A novel pH-sensitive fluorophore, DPP-BPDZ, functions as a reliable sensor in both solution and thin film states. Its fluorescence intensity decreases with increasing acidity, enabling sensitive pH detection and patternable sensor applications.
Area of Science:
- Materials Science
- Analytical Chemistry
- Organic Chemistry
Background:
- Development of sensitive and selective pH sensors is crucial for various analytical applications.
- Fluorophore-based sensors offer advantages in sensitivity and real-time monitoring.
- Existing pH sensors may face limitations in stability, sensitivity, or patternability.
Purpose of the Study:
- To explore the potential of a novel piperazine-substituted bipyridazine fluorophore (DPP-BPDZ) as a pH sensor.
- To investigate the sensing performance of DPP-BPDZ in solution and thin film formats.
- To develop a patternable fluorescent film sensor for localized pH detection.
Main Methods:
- Synthesis and characterization of the DPP-BPDZ fluorophore.
- Spectroscopic analysis (fluorescence spectroscopy) to evaluate pH sensitivity in solution.
- Fabrication of thin film sensors using DPP-BPDZ embedded in a PMMA host.
- Development of a patternable sensor by incorporating a photoacid generator (PAG).
- UV-induced patterning of fluorescent patterns on the film sensor.
Main Results:
- DPP-BPDZ exhibits high fluorescence quantum yield (0.63) in solution.
- Fluorescence intensity decreases linearly with increasing acetic acid concentration due to protonation.
- The thin film sensor shows an exponential decrease in fluorescence intensity with decreasing pH.
- Enhanced sensitivity observed below pH 4.5.
- Patternable sensors with 10 µm line width and high contrast were fabricated using UV light and PAG.
Conclusions:
- DPP-BPDZ is a promising pH-sensitive fluorophore for both solution-based and thin-film sensing applications.
- The developed thin film sensor demonstrates effective and sensitive pH detection.
- The integration of PAG enables the creation of patternable fluorescent sensors for advanced applications.
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