Synthesis of (tricyanofuran‐3‐ylmethylene)hydrazinyl thiazole‐containing chromophore: A study of its photophysical properties, solvatochromism, and TD‐DFT computations

Abstract

The chromophore 2-2- (3-cyano-5,5-dimethyl-4-((2-[thiazol-2-yl]hydrazono)methyl)furan-2(5H)-ylidene)malononitrile (TzHTCF) was prepared by diazo-coupling of diazotized 2-aminothiazole with 3-cyano-2-(dicyanomethylene)-4,5,5-trimethylfuran (TCF). The TzHTCF absorption solvatochromism, in different polarity solvents, demonstrated a ΔE max = +4.74 in which the positive sign implied the occurrence of a red shift and the TzHTCF lowest excited state was more polar than its ground state. In addition, the TzHTCF fluorescence spectrum produced a λ em in the 416-670 nm range and was more dependent on the solvent polarity than the absorption λ max , despite both exhibiting a red shift of 24 and 254 nm, respectively. To discover the Stokes shift (ΔνÞ behaviour of the TzHTCF derivative, Lippert-Mataga and linear solvation-energy relationship (LSER) formulations were utilized in which the LSER approach displayed better results than the Lippert-Mataga method (R 2 = 0.9931).Furthermore, the LSER showed that the absorption and fluorescence solvatochromic behaviours were dependent on the solvent's hydrogen-bond donor (α) and acceptor (β), along with the solvent's polarizability (π*). Moreover, DFT calculations showed that TzHTCF has a planar configuration and its simulated absorption and emission spectra in dimethyl sulphoxide revealed that λ max primarily originated from the HOMO!LUMO and HOMO-1!LUMO transitions, respectively.

Synthesis, characterization, and anticancer evaluation of novel 4‐hydrazinothiazole analogs

“…The varied activities of the carbon atoms on the thiazole ring have facilitated its utility as a vital synthon bearing various substituents [25,26]. The functionalization of the thiazole heterocycle leads to the synthesis of new molecular scaffolds with desirable physiochemical properties [27][28][29][30] for potential use as therapeutic drugs [31][32][33][34][35]. Different ketone derivatives have been extensively utilized as versatile reagents in the synthesis of diverse biologically active thiazoles [36][37][38][39][40].…”