Photoinduced Electron Transfer Switching Mechanism of a Naphthalimide Derivative with its Solvatochromic Behaviour: An Experimental and Theoretical Study with In Cell Investigations
| Autor: | Subhash Chandra Bhattacharya, Soumya Sundar Mati, Sourav Chowdhury, Krishnananda Chattopadhyay, Swadesh Ghosh, Dipti Singharoy |
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| Rok vydání: | 2017 |
| Předmět: |
Metal ions in aqueous solution
Analytical chemistry 010402 general chemistry Photochemistry 01 natural sciences Catalysis Photoinduced electron transfer Metal chemistry.chemical_compound mental disorders Molecule 010405 organic chemistry musculoskeletal neural and ocular physiology fungi Organic Chemistry Solvatochromism General Chemistry 0104 chemical sciences Nap Solvent chemistry visual_art visual_art.visual_art_medium human activities psychological phenomena and processes Derivative (chemistry) |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 23(65) |
| ISSN: | 1521-3765 |
| Popis: | The sole existence of a t-bone-shaped naphthalimide derivative [2-(2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)dione] (NAP), which gives rise to a photoinduced electron transfer (PET) mechanism, has been established using a combination of experimental and theoretical studies. In parallel an in vitro-in cell PET mechanism has also been shown. To understand the photophysics of NAP, solvent studies have been carried out in different solvents. In addition, theoretical calculations have been conducted to explain the spectroscopic properties through optimized structures. A "turn off" PET mechanism has also been observed in the presence of specific metal ions, namely, Cr3+ , Fe3+ and Hg2+ among a series of metal ions. Theoretical studies reveal that NAP-Cr3+ , NAP-Fe3+ and NAP-Hg2+ have their HOMO energy states lying in between a HOMO-LUMO energy state of the t-bone-type NAP molecule. On the contrary, the HOMO state of the other metal ion-NAP conjugate (NAP-Mn+ ) does not lie in between the HOMO-LUMO energy gap of the t-bone-type NAP molecule. Coupled with in vitro studies, in cell investigations reveal an enhancement of fluorescence intensity of NAP upon cytosolic metal sensing. Furthermore, a very high cell viability of NAP treated cells as tested by MTT assay and a fast permeation of the said compound as revealed by flow cytometry suggest NAP to be a potential candidate in metal sensing and bioimaging applications. |
| Databáze: | OpenAIRE |
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