Synthesis and molecular modelling of new donor-π-acceptor benzothiazole-carbazole-pyridine-based fluorescent chromophore

Abstract

The targeted benzothiazole-carbazole-pyridine dye (ThCzPy) was synthesized using a synthetic approach completed by the condensation of 6-(benzothiazol-2-yl)-3-formyl-9-hexyl-9H-carbazole (4) with 4-aminopyridine (5). The absorption and emission spectra of the chromophore ThCzPy, in DMSO, displayed good Stokes’ shift (Δν¯ = 4653 cm−1). The DFT configuration of the frontier molecular orbits in gas and solvated ground state (So) were compared to the solvated excited state (S1). Furthermore, the new chromophore’s antimicrobial efficacy was evaluated as minimum inhibitory concentration (MIC) against a panel of Gram’s positive, negative, and fungi using ampicillin and fluconazole as reference drugs, where it exhibited comparable activity. The SwissADME study revealed that ThCzPy has a bioavailability score 0.55 and meets Lipinski’s criteria for drug similarity.

Keywords

• Benzothiazole-carbazole-pyridine
• DFT
• Emission spectra
• Antimicrobial
• SwissADME