Indole-Boron-Difluoride Complexes with Anticancer and Fluorescence Properties
4
Issued Date
2025-01-01
Resource Type
ISSN
18614728
eISSN
1861471X
Scopus ID
2-s2.0-105002124757
Journal Title
Chemistry - An Asian Journal
Rights Holder(s)
SCOPUS
Bibliographic Citation
Chemistry - An Asian Journal (2025)
Suggested Citation
Vanthiya V., Jaroenchuensiri T., Faikhruea K., Pang-Eaem P., Plianjantuek N., Limpanuparb T., Vilaivan T., Aonbangkhen C., Chuawong P. Indole-Boron-Difluoride Complexes with Anticancer and Fluorescence Properties. Chemistry - An Asian Journal (2025). doi:10.1002/asia.202401698 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/109543
Title
Indole-Boron-Difluoride Complexes with Anticancer and Fluorescence Properties
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Abstract
Eight indole-boron-difluoride complexes were synthesized from 2,3-arylpyridylindole derivatives via Sonogashira coupling and Larock heteroannulation. These complexes exhibited distinct photophysical properties. Solvent polarity influenced their spectral behavior showing hypsochromic absorption, bathochromic emission shifts, and aggregation-induced emission (AIE) in mixed solvents. The ¹⁹F NMR shifts and photophysical properties, including excitation, emission maxima, and Stokes shift, correlated with Hammett substituent constants highlighting electronic effects on molecular properties. The synthesized complexes exhibited a range of intramolecular charge transfer (ICT) behaviors, as evidenced by their Lippert-Mataga parameters. TD-DFT calculations aligned with experimental data, offering insight into spectroscopic behavior. Notably, the indole-boron-difluoride complex bearing a methyl ester group exhibited significant anticancer activity against HeLa cells and potential for fluorescence imaging, indicating its promise for biomedical applications in cell imaging and therapy.