RESUMEN
Synthesis of three novel phenyl(1H-benzoimidazol-5-yl)methanone based fluorescent monoazo disperse dyes and their characterization by spectroscopic methods (1H NMR, 13C NMR, IR and MS) are presented. Insertion of phenyl(1H-benzoimidazol-5-yl)methanone moiety bring about induced fluorescence properties and enhanced photostability as compared to the previously reported analogues (CI Solvent Yellow 14, 4-diethylamino-2-hydroxy-1-diazobenzene and 7-(diethylamino)-4-hydroxy-3-(phenyldiazenyl)-2H-chromen-2-one). Synthesized phenyl(1H-benzoimidazol-5-yl)methanone based dyes exhibited red-shifted absorption maxima (497-516 nm), high molar extinction coefficients and are emitting in the far-red region (565-627 nm). Moreover, naphthalene-comprising dyes showed negative solvatochromism while N,N-diethylamine comprising dyes showed positive solvatochromism and are in good agreement with solvent polarity graphs and the computed energy levels of highest occupied and lowest unoccupied molecular orbitals. Synthesised dyes have better photostability (light fastness) and sublimation fastness on dyed polyester and nylon compared to reported analogues. DFT calculated energies, electrophilicity index and Frontier Molecular Orbitals (FMO's) enabled to evaluate the stabilities of azo and hydrazone forms of the dyes.
RESUMEN
Synthesis of novel 3,6-di(substituted quinoxalin) carbazole fluorophores by the condensation of 1,1'-(9-ethyl-9H-carbazole-3,6-diyl)bis(2-bromoethanone) with methyl, chloro and unsubstituted o-phenylenediamine is presented. Synthesized derivatives are well characterized by 1H NMR, 13C NMR, FTIR and Mass spectroscopy. Photophysical studies are carried out using solvents of varying polarities revealed positive solvatochromism and intramolecular charge transfer from carbazole (Donor) to quinoxalin (Acceptor). Intramolecular charge transfer properties are correlated by dipole moment changes and different polarity functions like Lippert-Mataga, Bilot-Kawski, Bakhshiev and Liptay plots with very good regression factors. Mulliken hush-analysis further support charge transfer characteristic. Linear and Nonlinear optical properties are explained by solvatochromic data using two-level quantum mechanical model and are correlated with computational calculations using density functional theory at B3LYP/6-31G(d) level. First hyperpolarizability value of all the synthesized compounds is found to be greater than urea by >333 times. Moreover, increase of hyperpolarizability values from non-polar to polar solvents are in good correlation with the significant charge transfer characteristic in polar solvents.
RESUMEN
Synthesis of novel benzophenone-based chemosensor is presented for the selective sensing of Sn2+ ion. Screening of competitive metal ions was performed by competitive experiments. The specific cation recognition ability of chemosensor towards Sn2+ was investigated by experimental (UV-visible, fluorescence spectroscopy, 1H NMR, 13C NMR, FTIR and HRMS) methods and further supported by Density Functional Theory study. The stoichiometric binding ratio and binding constant (Ka) for complex is found to be 1:1 and 1.50×104, respectively. The detection limit of Sn2+ towards chemosensor was found to be 0.3898ppb. Specific selectivity and superiority of chemosensor over another recently reported chemosensor is presented.