UV-visible light-induced photochemical synthesis of benzimidazoles by coomassie brilliant blue coated on W–ZnO@NH2 nanoparticles

Abstract

Heterogeneous photocatalysts proffer a promising method to actualize eco-friendly and green organic transformations. Herein, a new photochemical-based methodology is disclosed in the preparation of a wide range of benzimidazoles through condensation of o-phenylenediamine with benzyl alcohols in the air under the illumination of an HP mercury lamp in the absence of any oxidizing species catalyzed by a new photocatalyst W–ZnO@NH₂–CBB. In this photocatalyst, coomassie brilliant blue (CBB) is heterogenized onto W–ZnO@NH₂ to improve the surface characteristics at the molecular level and enhance the photocatalytic activity of both W–ZnO@NH₂ and CBB fragments. This unprecedented heterogeneous nanocatalyst is also identified by means of XRD, FT-IR, EDS, TGA-DTG, and SEM. The impact of some influencing parameters on the synthesis route and effects on the catalytic efficacy of W–ZnO@NH₂–CBB are also assessed. The appropriate products are attained for both the electron-withdrawing and electron-donating substituents in the utilized aromatic alcohols. Furthermore, preparation of benzimidazoles is demonstrated to occur mainly via a radical mechanism, which shows that reactive species such as ·O₂⁻, OH˙ and h⁺ would be involved in the photocatalytic process. Stability and reusability studies also warrant good reproducibility of the nanophotocatalyst for at least five runs. Eventually, a hot filtration test proved that the nanohybrid photocatalyst is stable in the reaction medium. Using an inexpensive catalyst, UV-vis light energy and air, as a low cost and plentiful oxidant, puts this methodology in the green chemistry domain and energy-saving organic synthesis strategies. Finally, the anticancer activity of W–ZnO nanoparticles is investigated on MCF7 breast cancer cells by MTT assay. This experiment reveals that the mentioned nanoparticles have significant cytotoxicity towards the selected cell line.