| Autor: |
Vats, Ravi Prakash, Pandey, Priyanka, Gupta, Shashwat, Gupta, Suchitra, Pal, Shyamal, Goel, Atul |
| Zdroj: |
Synthesis; Jan2025, Vol. 57 Issue 1, p115-124, 10p |
| Abstrakt: |
A new series of N -phenyl-carbazole (N-phCbz) appended pyranones were designed and synthesized using α-oxo-ketene- S , S -acetal under mild reaction conditions in good yields. The reactivity of donor-acceptor (D-A)-based 2 H -pyranones was utilized to develop their ring-transformed benzene-cored N -phenyl-carbazole derivatives. All the synthesized carbazole-based pyranones showed aggregation-induced emission (AIE) characteristics in 80–99% water fraction (fw) in DMSO. Among all the synthesized compounds, 6-(4-(9 H -carbazol-9-yl)phenyl)-4-(methylthio)-2-oxo-2 H -pyran-3-carbonitrile exhibited excellent AIE behavior with ca. 70-fold increase in fluorescence in 80% fw at 550nm. Furthermore, this compound showed exceptionally high fluorescence in nonpolar solvent (THF) as compared to polar solvents such as DMSO (ca. 200-fold increase in fluorescence). The DFT, DSC, and TGA analyses of the synthesized D-π-A compounds suggested the strong electron-donor ability of N-phCbz, with good thermal stability in the range of 231–393 °C. These N -phenyl-carbazole-appended pyranones with interesting AIE properties have great potential as probes for bioimaging applications as well as for optoelectronic materials. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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