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Updated: Dec 25, 2025
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Published on: August 1, 2016
Multistimuli-Responsive Fluorescent Organogelator Based on Triphenylamine-Substituted Acylhydrazone Derivative
Tianren Zhang1, Fangyi Chen1, Chunxue Zhang1
1Key Laboratory of Automobile Materials, Ministry of Education, College of Materials Science and Engineering, Jilin University, Changchun 130012, China.
A novel triphenylamine-based acylhydrazone derivative, TPAH-B8, forms organogels and exhibits fluorescence enhancement. This material displays remarkable multistimuli-responsive behaviors, including solvatochromism, mechanofluorochromism, and acidochromism.
Area of Science:
- Materials Science
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Triphenylamine derivatives are widely explored for their optoelectronic properties.
- Acylhydrazone compounds offer versatile synthetic pathways and tunable characteristics.
- Developing stimuli-responsive materials is crucial for advanced sensing and display technologies.
Purpose of the Study:
- To synthesize and characterize a new triphenylamine-based acylhydrazone derivative, TPAH-B8.
- To investigate the gelation behavior and fluorescence properties of TPAH-B8.
- To explore the multistimuli-responsive characteristics of TPAH-B8, including its response to solvents, mechanical force, and acids.
Main Methods:
- Synthesis of the triphenylamine-based acylhydrazone derivative (TPAH-B8).
- Organogel formation in cyclohexane via ultrasonic treatment.
- Spectroscopic analysis (UV-Vis absorption and fluorescence emission) to study optical properties.
- Investigation of solvatochromic, mechanofluorochromic, and acidochromic effects.
Main Results:
- TPAH-B8 successfully formed organogels in cyclohexane, exhibiting gelation-induced fluorescence enhancement attributed to J-aggregate formation.
- TPAH-B8 displayed a distinct solvatochromic effect, with emission color shifting from blue to cyan upon changing solvent polarity (cyclohexane to DMSO).
- Reversible mechanofluorochromism was observed; grinding the xerogel changed fluorescence from blue to cyan, reversible by annealing, linked to crystalline-amorphous state transitions.
- Acidochromic properties were demonstrated, with fluorescence color switching between states upon addition of trifluoroacetic acid (TFA) or triethylamine (TEA).
Conclusions:
- The synthesized TPAH-B8 exhibits significant multistimuli-responsive fluorescent properties.
- The material's responses are linked to molecular aggregation, solvent polarity, mechanical stress, and acid-base interactions.
- TPAH-B8 serves as a promising platform for developing novel multistimuli-responsive fluorescent materials for various applications.
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