Investigation of photophysical and electronic properties of aurone derivatives: Insights from spectroscopic techniques and density functional theory calculations.

This paper reports on a study of the photophysical properties, density functional theory (DFT) calculations, infrared (IR), ultraviolet (UV) and nuclear magnetic resonance (NMR) spectroscopic techniques of a series of aurone compounds. The photophysical properties were investigated using UV absorption and fluorescence spectroscopy in a dimethyl sulfoxide (DMSO) solution. Furthermore, the fluorescence quantum yields of the target compounds (1-24) were also investigated. Remarkably, these compounds revealed high quantum yields (Φ = 0.001-0.729) as compared to the already existing aurones in literature. The DFT calculations were performed to elucidate the electronic structure, energy levels and draw a comparison between experimental and theoretical findings. The simulated properties such as molecular frontier orbitals, the density of states, reactivity descriptors (GCRD), electrostatic potential distribution, transition density matrix, electron localization function (ELF) and localized orbital locator (LOL) have been calculated using DFT. The DFT calculations provided insight into the electronic structure and energy levels of the aurone compounds, while the IR and UV spectroscopy results shed light on their functional groups and electronic transitions, respectively. The results of this study contribute to a better understanding of the photophysical properties of aurone compounds and suggest their potential use in technological applications.

An AIE active fluorescence sensor for measuring Fe3+ in aqueous media and an iron deficiency anemia drug.

In this study, a new tetraphenylethene derivative bearing triazole and pyridine moieties (TPE-TAP) was synthesized using click chemistry. The fluorescence sensing properties of TPE-TAP were investigated in almost 100% aqueous media. For this purpose, first of all, structural characterization of the newly synthesized compound TPE-TAP was performed by NMR and HRMS analyses. Then, the optical behavior of TPE-TAP was investigated in different ratios of a THF-water mixture (0-98%). The obtained results showed that the best fluorescence for TPE-TAP was observed in the presence of 98% water in the medium. Then, the ion selectivity of TPE-TAP was determined using 19 different cations in the THF-water medium (2 : 98 v/v%). It was observed that among the cations studied, only Fe3+ quenched the fluorescence of TPE-TAP. The detection limit and binding constant values of TPE-TAP for Fe3+ were calculated as 1.3 µM and 26.65 M-2, respectively, from the graph results of the decrease in the fluorescence intensity of TPE-TAP in the presence of Fe3+ at different concentrations. In addition, the study investigating the selectivity of TPE-TAP in the presence of 18 cations other than Fe3+ showed that none of the studied cations interfered with Fe3+. Practical application of TPE-TAP was also carried out using a commercial iron drug. All results showed that TPE-TAP is a fluorometric sensor highly selective, sensitive, and suitable for practical application for Fe3+ ions in aqueous medium.

Deciphering binding mechanism between bovine serum albumin and new pyrazoline compound K4.

The binding mechanism of a new and possible drug candidate pyrazoline derivative compound K4 and bovine serum albumin (BSA) was investigated in buffer solution (pH 7.4) using ultraviolet-visible light absorption and steady-state and synchronous fluorescence techniques. The fluorescence intensity of BSA was quenched in the presence of K4. The quenching process between BSA and K4 was examined at four different temperatures. Decrease of the quenching constants calculated using the Stern-Volmer equation and at increasing temperature suggested that the interaction BSA-K4 was realized through a static quenching mechanism. Synchronous fluorescence measurements suggested that K4 bounded to BSA at the tryptophan region. Fourier transform infrared spectroscopy results showed that there was no significant change in polarity around the tryptophan residue The forces responsible for the BSA-K4 interaction were examined using thermodynamic parameters. In this study, the calculated negative value of ΔG, the negative value of ΔH and the positive value of ΔS pointed to the interaction being through spontaneous and electrostatic interactions that were dominant for our cases. This study provides a very useful in vitro model to researchers by mimicking in vivo conditions to estimate interactions between a possible drug candidate or a drug and body proteins.

Investigation of Solvent Effects on Photophysical Properties of New Aminophthalimide Derivatives-Based on Methanesulfonate.

Novel aminophthalimide derivatives were synthesized starting from (3aR,7aS)-2-(2-hydroxypropyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione (9) , and solvent effects on the photo-physical properties of these newly synthesized aminophthalimide derivatives (compounds 14 and 15) were investigated using UV-Vis absorption spectroscopy, steady-state and time-resolved fluorescence measurements. Both absorption and fluorescence spectra exhibited bathochromic shift with the increased polarity of the solvents for both molecules. Solute-solvent interactions were analyzed using the Lippert-Mataga and Bakhshiev polarity functions, and Kamlet-Taft and Catalan multiple linear regression approaches. The results revealed that these two molecules experienced specific interactions. Furthermore, photo-physical parameters were calculated for both molecules in all of the solvents, such as the fluorescence quantum yield, fluorescence lifetime, radiative (kr) and non-radiative (knr) rate constant values. It was observed that the fluorescence quantum yield values decreased linearly with increasing solvent polarity. This study proved the new dyes including isopropyl methanesulfonate group displayed different behavior from previous studies of aminophthalimide derivatives in water. It was recommended that these new dyes having interesting properties by changing solvent can be used various applications such as environmentally sensitive fluorescent probes, labels in biology, laser industry.

Rhodamine 101-graphene oxide composites in aqueous solution: the fluorescence quenching process of rhodamine 101.

The interaction of rhodamine 101 (Rh101) with graphene oxide (GO) in aqueous dispersion was examined using advanced spectroscopic techniques. Rh101-GO composites in water were easily prepared by mixing an aqueous solution of both components since GO sheets interacted with the cationic dyes via π-π and electrostatic cooperative interactions. In the composites, the fluorescence of Rh101, which was a well-known laser dye with a high fluorescence quantum yield, could be efficiently quenched by GO. The quenching mechanism of Rh101 by GO sheets was evaluated by the Stern-Volmer (SV) equation and the time-resolved fluorescence studies. The results revealed that the fluorescence quenching of Rh101 by GO in the aqueous dispersion is due to the static quenching mechanism. The formation of the Rh101-GO composites at various pH values was spectroscopically monitored, and the spectroscopic results revealed that the composites were formed at the pH values studied except in the strong acidic media (pH ≈ 2). The interaction of Rh101 with GO in aqueous solution was spectroscopically followed in the presence of SDS (sodium dodecyl sulphate) at the surfactant concentrations above and below the CMC (critical micelle concentration). The fluorescence studies revealed that the fluorescence of Rh101 in the aqueous solution remarkably increased at the surfactant concentration forming the micelle of SDS.

Spectroscopic studies on the interaction of fluorescein and safranine T in PC liposomes.

In this study, the fluorescence quenching of fluorescein by safranine T in liposome media had been investigated systematically by fluorescence spectroscopy, UV-vis absorption spectroscopy and fluorescence decay lifetime measurements. The spectroscopic data were analyzed using a Stern-Volmer equation to determine the quenching process. The experimental results showed that the intrinsic fluorescence of fluorescein was strongly quenched by safranine T, and that the quenching mechanism was considered as static quenching by forming a ground-complex. The Stern-Volmer quenching constant Ksv, and the bimolecular quenching constant Kq were estimated. The distances between the donor (fluorescein) and the acceptor (safranine T) were calculated according to the Förster non-radiation energy transfer theory. In addition, the partition coefficient of the safranine T (Kp) in the L-egg lecithin phosphatidylcholine liposomes was also calculated by utilizing the fluorescence quenching.