Vanthiya V.Jaroenchuensiri T.Faikhruea K.Pang-Eaem P.Plianjantuek N.Limpanuparb T.Vilaivan T.Aonbangkhen C.Chuawong P.Mahidol University2025-04-152025-04-152025-01-01Chemistry - An Asian Journal (2025)18614728https://repository.li.mahidol.ac.th/handle/123456789/109543Eight 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.ChemistryBiochemistry, Genetics and Molecular BiologyArticleSCOPUS10.1002/asia.2024016982-s2.0-1050021247571861471X