A combined theoretical and experimental investigation on the solvatochromism of ESIPT3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde.

Excited state intramolecular proton transfer inspired 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde, showing solid state fluorescence has been synthesized. Existence of excited state intramolecular proton transfer process between carbonyl group and phenolic OH group has been theoretically predicted using computational method. Density functional theory and time dependent density functional theory computations have been used to investigate structural parameters and understand the photophysical properties of the synthesized carbaldehyde. The photophysical properties of carbaldehyde were evaluated using UV-Visible and fluorescence spectroscopy and are found to be very sensitive to the microenvironment such as solvent polarity and pH. The experimental absorption-emission a results are correlated with the computed values. The increase in the dipole moment of A2-Keto(*) than A2-Enol(*) suggested the presence of keto form in the excited state and which is responsible for the single fluorescence emission with a large Stokes shift in all solvents.

TDDFT investigation of the electronic structures and photophysical properties of fluorescent extended styryl push-pull chromophores containing carbazole unit.

Push-pull chromophores attached to carbazole based π-conjugating spacers bearing N-alkylamino donors, cyanovinyl and carbethoxy acceptors have been studied by the means of UV-Visible measurements. The intramolecular charge transfer (ICT) of these π-conjugated systems has also been tested by investigating the ability of the solute molecules to undergo shifts in their fluorescence emission maxima with increasing solvent polarity. Density Functional Theory [B3LYP/6-31G(d)] and Time Dependent Density Functional Theory [TD-B3LYP/6-31G(d)] computations have been used to have more understanding of the structural, molecular, electronic and photophysical parameters of push-pull dyes. The largest wavelength difference between the experimental and computed electronic absorption maxima was 45 nm. For emission, a largest difference of 61 nm was observed. The ground state and excited state dipole moments in different solvents were determined using experimental solvatochromic data and computed Onsager radii. The dipole moments of the molecules in the excited state were observed to be higher than in the ground state.

Synthesis, photo-physical and DFT studies of ESIPT inspired novel 2-(2',4'-dihydroxyphenyl) benzimidazole, benzoxazole and benzothiazole.

Novel ESIPT inspired benzimidazole, benzoxazole and benzothiazole were synthesized from 2,4-dihydroxy benzoic acid and 1,2-phenelenediamine, 2-aminophenol, and 2-aminothiophenol respectively. The synthesized 2-(2',4'-dihydroxyphenyl) benzimidazole, benzoxazole and benzothiazole are fluorescent and the emission characteristic are very sensitive to the micro-environment. They show a single absorption and dual emission with large Stokes shift originating from excited state intramolecular proton transfer. The absorption-emission characteristics of all these compounds are studied as a function of pH. The change in the electronic transition, energy levels, and orbital diagrams of synthesized compounds were investigated by the molecular orbital calculation and were correlated with the experimental spectral emission. Experimental absorption and emission wavelengths are in good agreement with those predicted using the Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT) [B3LYP/6-31G(d)].

Synthesis and photo-physical characteristics of ESIPT inspired 2-substituted benzimidazole, benzoxazole and benzothiazole fluorescent derivatives.

Novel 2-(1H-benzimidazol-2-yl)-5-(N,N-diethylamino) phenol, 2-(1,3-benzoxazol-2-yl)-5-(N,N-diethylamino) phenol, 2-(1,3-benzothiazol-2-yl)-5-(N,N-diethylamino) phenol and their derivatives have been synthesized from p-N,N-diethyl amino salicylaldehyde with different substituted o-phenylenediamine or o-aminophenol or o-aminothiophenol and their photo-physical properties were studied. Effects of solvent polarity in the absorption-emission properties of synthesized compounds were investigated. All these compounds shows excited state intra-molecular proton transfer pathway having single absorption and dual emission characteristics. The fluorescent compounds were characterised by FT-IR, (1)HNMR, (13)C NMR and Mass spectral analysis. TGA analysis showed these compounds are thermally stable up to 200 °C.

Synthesis of new ESIPT-fluorescein: photophysics of pH sensitivity and fluorescence.

ESIPT-inspired benzimidazolyl substituted fluorescein dyes were synthesized. PH-sensitivity was determined by the photophysical property measured at a physiological possible pH range. Fluorescence quantum efficiency values were calculated independently at two different emissions. A rational relationship is defined between fluorescence quantum efficiency and calculated HOMO energy.

Synthesis, Characterization, Thermal Properties, and Antimicrobial Activities of 5-(Diethylamino)-2-(5-nitro-1H-benzimidazol-2-yl)phenol and Its Transition Metal Complexes.

Synthesis and antimicrobial activities of new metal [Co(II), Cu(II), Ni(II), and Fe(II)] complexes from 5-(diethylamino)-2-(5-nitro-1H-benzimidazol-2-yl)phenol are described. The newly synthesized ligands were characterized by IR, (1)H NMR, and LC-MS analysis, and metal-ligand complex formations were confirmed by using atomic absorption spectroscopy and elemental analysis. All complexes show significant in vitro antibacterial activities against E. coli and S. aureus strains and in vitro antifungal activity against C. albicans and A. niger strains by using serial dilution method. The antibacterial activities were expressed as the minimum inhibitory concentration (MIC) in µg/mL. Thermal properties and electrochemical behavior of novel transition metal complexes have been studied.