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Triazole-Based Functionalized Olygo(Arylene Ethynylene)s-Synthesis and Properties
Anastasia I Govdi1, Vasiliy V Menchikov1, Ilya E Kolesnikov2
1Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.
Molecules (Basel, Switzerland)
|December 11, 2025
Summary
New oligo(arylene ethynylene)s (OAEs) were synthesized using the retro-Favorskii reaction. These OAEs exhibit tunable fluorescence properties, with aggregate-induced emission enhancement observed in aqueous organic solutions.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Oligo(arylene ethynylene)s (OAEs) are conjugated polymers with potential applications in organic electronics and photonics.
- The synthesis and photophysical properties of OAEs are of significant interest for developing new functional materials.
Purpose of the Study:
- To synthesize novel OAEs incorporating 1,2,3-triazole units and explore their fluorescence characteristics.
- To investigate the effect of substituents and solvent polarity on the emission properties of these OAEs.
- To study the phenomenon of aggregate-induced emission enhancement (AIEE) in aqueous organic media.
Main Methods:
- Synthesis of OAEs via the retro-Favorskii reaction, utilizing 4,5-(diethynylaryl)-1,2,3-triazoles.
- Characterization of synthesized OAEs using spectroscopic techniques (fluorescence spectroscopy).
- Investigation of solvent effects on emission spectra and quantum yields in various organic solvents and aqueous mixtures.
- Dynamic light scattering (DLS) to study aggregate formation.
Main Results:
- OAEs with trimethoxyphenyl substituents showed high fluorescence quantum yields (up to 88%) in THF.
- Minimal solvent polarity effect on emission for trimethoxyphenyl derivatives.
- Significant red shifts and hypochromic effects observed for OAEs with para-dimethylaminophenyl groups in polar solvents.
- Aggregate-induced emission enhancement (AIEE) observed in aqueous organic solutions, particularly in DMSO/water mixtures.
- DLS confirmed the formation of nanoscale aggregates in aqueous organic media.
Conclusions:
- The retro-Favorskii reaction is an effective method for synthesizing novel OAEs with tunable photophysical properties.
- The electronic nature of substituents significantly influences the emission behavior of OAEs in different solvent environments.
- The synthesized OAEs demonstrate potential for applications where aggregate formation leads to enhanced fluorescence, such as in sensing or imaging.
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