Base-Free Synthesis and Photophysical Properties of New Schiff Bases Containing Indole Moiety.

Schiff bases represent an essential class in organic chemistry with antitumor, antiviral, antifungal, and antibacterial activities. The synthesis of Schiff bases requires the presence of an organic base as a catalyst such as piperidine. Base-free synthesis of organic compounds using a heterogeneous catalyst has recently attracted more interest due to the facile procedure, high yield, and reusability of the used catalyst. Herein, we present a comparative study to synthesize new Schiff bases containing indole moieties using piperidine as an organic base catalyst and Au@TiO2 as a heterogeneous catalyst. In both methods, the products were isolated in high yields and fully characterized using different spectral analysis techniques. The catalyst was reusable four times, and the activity was slightly decreased. The presence of Au increases the number of acidic sites of TiO2, resulting in C=O polarization. Yields of the prepared Schiff bases in the presence of Au@TiO2 and piperidine were comparable. However, Au@TiO2 is an easily separable and recyclable catalyst, which would facilitate the synthesis of organic compounds without applying any hazardous materials. Furthermore, the luminescence behavior of the synthesized Schiff bases exhibited spectral shape dependence on the substituent group. Interestingly, the compounds also displayed deep-blue fluorescence with Commission Internationale de l'Éclairage (CIE) coordinates of y < 0.1. Thus, these materials may contribute to decreasing the energy consumption of the emitting devices.

Hierarchical porous zeolitic imidazolate frameworks (ZIF-8) and ZnO@N-doped carbon for selective adsorption and photocatalytic degradation of organic pollutants.

Removing organic contaminants such as dyes from water is essential to purify wastewater. Herein, zeolitic imidazolate framework-8 (ZIF-8) and ZnO@N-doped C are reported as effective adsorbents and photocatalysts for the adsorption and degradation of organic dyes. The materials showed effective and selective adsorption toward anionic dyes such as methyl blue (MeB) dye in the presence of fluorescein (FLU) dye. The adsorption capacities of ZnO@N-doped C for MeB and FLU dyes are 900 mg g-1 and 100 mg g-1, respectively. According to UV-Vis diffuse reflectance spectroscopy (DRS) data, ZnO@N-doped C has a lower bandgap (2.07 eV) than ZIF-8 (4.34 eV) and ZnO (3.12 eV). Thus, ZnO@N-doped C serves as an effective photocatalyst for the degradation of both dyes under UV exposure. The degradation efficiency capacity of the dye (50 mg L-1) is >90% using 200 mg L-1 of the photocatalyst. The mechanism of adsorption and photocatalysis is investigated. The photodegradation pathway of the dye involved the generation of oxidative hydroxy radicals (OH˙), which can degrade the dyes. The degradation products of FLU were recorded using mass spectrometry.

A highly efficient photochemical bromination as a new method for preparation of mono, bis and fused pyrazole derivatives.

N-Bromosuccinimide (NBS) was found to afford photochemical bromination of N-substituted 3-methyl-2-pyrazolin-5-one in chloroform solution. The nature of the products formed was found to be highly dependent on the photolysis time and on the type of N-substituted 3-methyl-2-pyrazolin-5-one. The reaction of substituted 2-pyrazolin-5-ones with NBS in the absence of light yielded in all cases a mixture of N-substituted 3-methyl-4-bromo- (and -4,4-dibromo-) 2-pyrazolin-5-ones. The mechanism of photobromination was illustrated. Separation of all of the products was achieved using column chromatography. The chemical structure of all of the products was assigned by elemental analysis, IR, 1H NMR and GC-MS measurements.