Active Bromoaniline-Aldehyde Conjugate Systems and Their Complexes as Versatile Sensors of Multiple Cations with...

Two fluorescence active bromoaniline-based Schiff base chemosensors, namely, (E)-4-bromo-2-(((4-bromophenyl)imino)methyl)phenol (HL ) and (E)-2-(((4-bromophenyl)imino)methyl)phenol (HL ), have been employed for the selective and notable detection of Cu²⁺ and Zn²⁺ ions, respectively, with the simultaneous formation of two new metal complexes [Cu(L₁)₂] (1) and [Zn(L₂)₂] (2). X-ray single crystal analyses indicate that complexes 1 and 2 are tetra-coordinated systems with substantial CH...π/π...π stacking interactions in the solid-state crystal structures. These two complexes are exploited for the next step detection of Al³⁺ and Hg²⁺ where complex 2 exhibits impressive results via turn-off fluorescence quenching in (DMSO/H₂O) HEPES buffer medium. The sensing phenomena are optimized by UV-vis spectral analyses as well as theoretical calculations (density functional theory and time-dependent density functional theory). The combined detection phenomena of the ligand (HL ) and complex 2 are exclusively utilized for the first time to construct a molecular memory device, intensifying their multisensoric properties. Furthermore, the DNA- and human serum albumin (HSA)-binding efficacies of these two complexes are examined by adopting electronic and fluorometric titration methods. Complex 2 shows a higher DNA-binding ability in comparison with complex 1, whereas in the case of HSA, the reverse situation is observed. Finally, the binding modes of both the complexes with DNA and HSA have been investigated through molecular docking studies, suggesting good agreement with the experimental results.