Synthesis, characterization, antibacterial activity and molecular docking of novel dicyanodihydrofuran-based push-pull fluorophores.

Novel push-pull fluorescent molecules based on dicyanodihydrofuran that have remarkable molar extinction coefficients have been created and described. The fluorophores were synthesized over Knoevenagel condensation in arid pyridine at room temperature using acetic acid as catalytic agent. Meanwhile, condensation reaction was performed over the activated methyl-containing dicyanodihydrofuran with 3°-amine-containing aromatic aldehyde. The molecular structures for the synthesized fluorophores were proved by various spectral techniques such as 1 H, 13 C NMR, FT-IR, and (C, H, N) analysis. UV-Vis absorption and emission spectra of the prepared fluorophores revealed high extinction coefficient, which was monitored to be affected by the type of the aryl (phenyl and thiophene)-vinyl bridge in conjugation with the 3° amine donor moiety. The substituents bonded to the tertiary amine, aryl and alkyl groups, were found to affect on the absorbance maximum wavelength. Meanwhile, the synthesized dicyanodihydrofuran analogues were checked to inspect antimicrobial effectiveness. Derivatives 2b, 4a and 4b labeled reasonable activity toward (+ve) Gram bacteria rather than (-ve) Gram bacteria relative to amoxicillin drug reference. Meanwhile, the molecular docking stimulation was pragmatic to explore their binding interactions toward (PDB code: 1LNZ).