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Photoinduced Electron Transfer Switching Mechanism of a Naphthalimide Derivative with its Solvatochromic Behaviour: An Experimental and Theoretical Study with In Cell Investigations
- Source :
- Chemistry (Weinheim an der Bergstrasse, Germany). 23(65)
- Publication Year :
- 2017
-
Abstract
- 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.
- Subjects :
- 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)
Subjects
Details
- ISSN :
- 15213765
- Volume :
- 23
- Issue :
- 65
- Database :
- OpenAIRE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Accession number :
- edsair.doi.dedup.....240df6414b65359e3f59be95cb2173ea