Presentation Information
[P03-327]Design and Synthesis of Novel AIEE-Active 3,7-Diarylpyrazolo[1,5-a]pyridine Luminogens: Tunable Photoluminescence and β-Cyclodextrin Encapsulation
○Jean-Ho Chu1, Bing-Han Zhuang1, Wen-Sheng Tsui1, Kun-Chi Tsai1 (1. Department of Applied Science, National Taitung University (Taiwan))
Keywords:
pyrazolo[1,5-a]pyridines,aggregation-induced enhanced emission (AIEE),cyclodextrins,bio-imaging applications
[Purpose]
This study is to design and synthesize a series of novel aggregation-induced enhanced emission (AIEE)-active 3,7-diarylpyrazolo[1,5-a]pyridine luminogens, to modulate their photoluminescence properties through molecular structural modification, and to investigate their host–guest encapsulation behavior with β-cyclodextrin (β-CD) for potential applications in aqueous fluorescent bioimaging.
[Method]
A Pd-mediated C(3,7)–H activation/arylation strategy was employed to efficiently synthesize a series of 3,7-diarylpyrazolo[1,5-a]pyridine derivatives. Their photophysical properties were systematically investigated using UV–Vis absorption and photoluminescence (PL) spectroscopy, including measurements of fluorescence quantum yields. The AIEE behavior was evaluated in THF/water mixtures with varying water fractions. In addition, host–guest complexation with β-cyclodextrin was examined in aqueous solution.
[Results]
The results demonstrate that the emission wavelengths of the 3,7-diarylpyrazolo[1,5-a]pyridine luminogens can be effectively tuned from 480 to 570 nm by introducing electron-donating and electron-withdrawing substituents. These luminogens exhibit pronounced AIEE behavior in THF/water mixed solvent systems with high water content. Furthermore, the compounds were successfully encapsulated by β-cyclodextrin to form stable 1:2 host–guest complexes in aqueous solution.
[Consideration]
Encapsulation by β-cyclodextrin significantly improves the aqueous dispersibility and stability of the hydrophobic AIEE-active luminogens while preserving their emissive properties. This host–guest strategy provides an effective approach to enhancing the applicability of AIEE luminogens in water-based and biologically relevant environments.
[Conclusion]
A facile and efficient synthetic approach has been developed to access AIEE-active 3,7-diarylpyrazolo[1,5-a]pyridine luminogens with tunable photoluminescence. Their successful encapsulation by β-cyclodextrin affords stable host–guest complexes in aqueous media, highlighting their promising potential for applications in aqueous fluorescent bioimaging.
This study is to design and synthesize a series of novel aggregation-induced enhanced emission (AIEE)-active 3,7-diarylpyrazolo[1,5-a]pyridine luminogens, to modulate their photoluminescence properties through molecular structural modification, and to investigate their host–guest encapsulation behavior with β-cyclodextrin (β-CD) for potential applications in aqueous fluorescent bioimaging.
[Method]
A Pd-mediated C(3,7)–H activation/arylation strategy was employed to efficiently synthesize a series of 3,7-diarylpyrazolo[1,5-a]pyridine derivatives. Their photophysical properties were systematically investigated using UV–Vis absorption and photoluminescence (PL) spectroscopy, including measurements of fluorescence quantum yields. The AIEE behavior was evaluated in THF/water mixtures with varying water fractions. In addition, host–guest complexation with β-cyclodextrin was examined in aqueous solution.
[Results]
The results demonstrate that the emission wavelengths of the 3,7-diarylpyrazolo[1,5-a]pyridine luminogens can be effectively tuned from 480 to 570 nm by introducing electron-donating and electron-withdrawing substituents. These luminogens exhibit pronounced AIEE behavior in THF/water mixed solvent systems with high water content. Furthermore, the compounds were successfully encapsulated by β-cyclodextrin to form stable 1:2 host–guest complexes in aqueous solution.
[Consideration]
Encapsulation by β-cyclodextrin significantly improves the aqueous dispersibility and stability of the hydrophobic AIEE-active luminogens while preserving their emissive properties. This host–guest strategy provides an effective approach to enhancing the applicability of AIEE luminogens in water-based and biologically relevant environments.
[Conclusion]
A facile and efficient synthetic approach has been developed to access AIEE-active 3,7-diarylpyrazolo[1,5-a]pyridine luminogens with tunable photoluminescence. Their successful encapsulation by β-cyclodextrin affords stable host–guest complexes in aqueous media, highlighting their promising potential for applications in aqueous fluorescent bioimaging.
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