Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes
| Autor: | Brenno A. D. Neto, José R. Corrêa, Juliano A. Chaker, Paulo Eduardo Narcizo de Souza, Daniel F. S. Machado, Elaine R Sodre, Valter H. Carvalho-Silva, Claudia C. Gatto, Talita de A. Fernandes, Bruna C. Guido |
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| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Relaxation (NMR) Kinetics 010402 general chemistry Photochemistry 01 natural sciences Fluorescence 0104 chemical sciences law.invention Spectrometry Fluorescence Dynamic light scattering law Excited state Lipid droplet Thiadiazoles Density functional theory Electron paramagnetic resonance Fluorescent Dyes |
| Zdroj: | The Journal of Organic Chemistry. 85:12614-12634 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.0c01805 |
| Popis: | An aggregation-induced emission enhancement (AIEE) effect in fluorescent lipophilic 2,1,3-benzothiadiazole (BTD) derivatives and their organic nanoaggregates were studied. A set of techniques such as single-crystal X-ray, dynamic light scattering (DLS), electron paramagnetic resonance (EPR), UV-vis, fluorescence, and density functional theory (DFT) calculations have been used to decipher the formation/break (kinetics), properties, and dynamics of the organic nanoaggregates of three BTD small organic molecules. An in-depth study of the excited-state also revealed the preferential relaxation emissive pathways for the BTD derivatives and the dynamics associated with it. The results described herein, for the first time, explain the formation of fluorescent BTD nanoaggregate derivatives and allow for the understanding of their dynamics in solution as well as the ruling forces of both aggregation and break processes along with the involved equilibrium. One of the developed dyes could be used at a nanomolar concentration to selectively stain lipid droplets emitting an intense and bright fluorescence at the red channel. The other two BTDs could also stain lipid droplets at very low concentrations and were visualized preferentially at the blue channel. |
| Databáze: | OpenAIRE |
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