RESUMO
Fluorescent organotin compounds are useful in sensing, optoelectronic devices, and in vitro bioimaging. Although in vitro fluorescence bioimaging shows low resolution at room temperature, a better resolution is possible at cryotemperatures. Therefore, the search for new cryoluminescent materials with potential application in high-resolution fluorescence bioimaging remains a great challenge. Herein, we report the cryoluminescence properties of two fluorescent bis-organotin compounds, namely, BisNTHySnBu2 (5) and BisNTHySnPh2 (6), synthesized via microwave irradiation. All compounds were fully characterized using 1H, 13C, and 119Sn NMR spectroscopy, Raman spectroscopy, IR spectroscopy, and HR-MS. The 119Sn δ and 3J(1H,119Sn) of 5 and 6 indicate that two Sn-ligands are chemically and electronically equivalent, as confirmed by cyclic voltammetry. The crystal structure of 6 showed pentacoordinate tin atoms with skeleton ligands. The study of self-assembled monolayers of both Sn-complexes via STM microscopy revealed a similar supramolecular packing in lamella-like patterns, adopting a face-on arrangement, where molecules stay flat lying on HOPG in accordance with the height profile of closely packed monolayers on graphite of about 0.33 nm thickness. However, only the Sn complex 6, which bears phenyls, covers large surface areas. The photophysical properties of bis-organotin compounds were also investigated in solution (room and low temperatures) and in the solid state. Good luminescence properties in solutions with fluorescence quantum yields (Φ) of approximately 35% and 50% were found. Despite this, Φ is quenched in the solid state because of aggregation, as supported by solvent/non solvent fluorescence studies, which is in agreement with STM and AFM investigation.
RESUMO
Fluorescent bioimaging is an excellent tool in cellular biology, and it will be a powerful technique in modern medicine as a noninvasive imaging technology where tumoral and normal cells must be distinguished. One of the differences between normal and cancer cells is the intracellular pH. Therefore, the design and synthesis of pH-responsive fluorescent materials are required. Organotin Schiff bases showed halofluorochromic behavior in solution. Microwave-assisted synthesis showed better reaction times and chemical yields compared with conventional heating. All compounds were fully characterized by spectroscopic and spectrometric techniques. The halofluorochromism study showed that some molecules in acidic media have the maximum luminescence intensity due to protonation. All the fluorescent tin complexes showed cell staining on hepatocyte and MCF-7 cells by confocal microscopy. The theoretical study has enabled us to rationalize the optical properties and the halofluorochromism for compounds 1 and 2 synthesized in this work. Our results showed that the emission decrease, in the acid and basic media for compounds 1 and 2, respectively, is caused by intramolecular charge transfer (ICT) deactivation.
Assuntos
Corantes Fluorescentes/química , Compostos Orgânicos de Estanho/química , Bases de Schiff/química , Sobrevivência Celular/efeitos dos fármacos , Teoria da Densidade Funcional , Hepatócitos/citologia , Hepatócitos/patologia , Humanos , Concentração de Íons de Hidrogênio , Células MCF-7 , Microscopia Confocal , Conformação Molecular , Compostos Orgânicos de Estanho/farmacologia , Espectrometria de FluorescênciaRESUMO
The progress made by the scientific community in emerging photovoltaic technologies over the past two decades has been outstanding. Numerous methods have been developed for the preparation of hybrid organic-inorganic perovskite solar cells. The power conversion efficiency has been up to 14% by a one-step vacuum deposition technique. A serious concern is the toxicity of the materials. In this review, several methods aimed at resolving these problems to some extent have been compiled, including eco-friendly synthesis. Further efficiency enhancements are expected following optimization, and a better fundamental understanding of the internal electron charge transfer, electron-hole diffusion to the corresponding layers, flexibility, and stability-dependent bandgaps is reported. This paper explores the green synthesis of organic-inorganic perovskites for industrialization. Concerning the above facts, a simple low-cost model called "dispersed photovoltaic cells" is presented.
RESUMO
A series of eight new organotin compounds derived from Schiff bases has been prepared by a multicomponent reaction from 2-hydroxy-1-naphthaldehyde or 4-substituted-2-hydroxybenzalhedyde, benzhydrazine, and the corresponding diorganotin oxide (R2SnO, R = nBu or Ph). All of the compounds were fully characterized by NMR (1H, 13C, and 119Sn), IR, UV/vis, elemental analyses and fluorescence spectroscopy. The crystal structures for some organotin compounds were determined by single crystal X-ray diffraction analysis. All of the compounds display fluorescence at room temperature with quantum yields of about 2 × 10-4 to 0.56. The cytotoxic activity and cellular imaging studies were carried out with the newly synthesized compounds. To the best of our knowledge, this is the first report of organotin compounds with Schiff base ligands investigated for fluorescence bioimaging (FBI).