Synthesis, electrochemical, optical and biological properties of new carbazole derivatives

Abstract

Carbazole skeleton is the key structural motif of many biologically active compounds including synthetic and natural products. Based on the (E)-2-(2-(4-9H-carbazol-9-yl)benzylidene) hydrazinyl)thiazole as skeleton, three novel carbazole dyes were synthesized. The scientific analysis includes the effect of changing the strength of the activating substituents and their exchange for the deactivating substituent on the chemical and biological properties. The presented research showed a significant influence of the CH₃, OCH₃ and CH₂COOC₂H₅ groups on the spectral properties of the tested derivatives. Their significant influence is also visible in electrochemical, nonlinear-optic and biological properties. The study also included the analysis of the use of the presented derivatives as potential fluorescent probes for in vivo and in vitro tests. Quantum-chemical calculations complement the conducted experiments.

Keywords: Bioimaging; Carbazole dyes; DFT; Nonlinear optical properties; Optical functional materials; Photo-optical properties; Protein affinity; Toxicology.