Probing the ESIPT process in 2-amino-1,4-naphthoquinone: thermodynamics properties, solvent effect and chemometric analysis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18450%2F16%3A50004663" target="_blank" >RIV/62690094:18450/16:50004663 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1007/s00214-015-1786-4" target="_blank" >http://dx.doi.org/10.1007/s00214-015-1786-4</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s00214-015-1786-4" target="_blank" >10.1007/s00214-015-1786-4</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Probing the ESIPT process in 2-amino-1,4-naphthoquinone: thermodynamics properties, solvent effect and chemometric analysis

Popis výsledku v původním jazyce

The developing of fluorescent probes for disease diagnosis is a very important task, which favors precision in the diagnosis and success in the treatment. Recently, amino-naphthoquinone derivatives showed to be efficient fluorescent probes for disease diagnosis. Those compounds exhibit excited-state intramolecular proton transfer (ESIPT), which is the main mechanism responsible for their use as fluorescent probes. The understanding of the ESIPT mechanism for naphthoquinones is an important way of developing more efficient and selective fluorescent probes. In this work, the ESIPT process for ANQ was performed at the TD-DFT/CAM-B3LYP/DGTZVP and DFT/ B3LYP/DGTZVP level for the electronic and geometric studies. These parameters were selected for the PCA analysis. The solvent effect was investigated by using PCM and IEF-PCM in chloroform, water and methanol. 2-Amino-1,4-naphthoquinone (ANQ) showed blue emission for fluorescence, having keto–keto* absorption at 4.50 eV and the enol–enol* decay at 2.75 eV. The solvent effect was evaluated, and the ESIPT process of ANQ was favorable in nonpolar and polar solvents. Furthermore, the thermodynamics properties showed that the ESIPT is favorable with a proton transfer equilibrium constant of ~105.

Název v anglickém jazyce

Probing the ESIPT process in 2-amino-1,4-naphthoquinone: thermodynamics properties, solvent effect and chemometric analysis

Popis výsledku anglicky

The developing of fluorescent probes for disease diagnosis is a very important task, which favors precision in the diagnosis and success in the treatment. Recently, amino-naphthoquinone derivatives showed to be efficient fluorescent probes for disease diagnosis. Those compounds exhibit excited-state intramolecular proton transfer (ESIPT), which is the main mechanism responsible for their use as fluorescent probes. The understanding of the ESIPT mechanism for naphthoquinones is an important way of developing more efficient and selective fluorescent probes. In this work, the ESIPT process for ANQ was performed at the TD-DFT/CAM-B3LYP/DGTZVP and DFT/ B3LYP/DGTZVP level for the electronic and geometric studies. These parameters were selected for the PCA analysis. The solvent effect was investigated by using PCM and IEF-PCM in chloroform, water and methanol. 2-Amino-1,4-naphthoquinone (ANQ) showed blue emission for fluorescence, having keto–keto* absorption at 4.50 eV and the enol–enol* decay at 2.75 eV. The solvent effect was evaluated, and the ESIPT process of ANQ was favorable in nonpolar and polar solvents. Furthermore, the thermodynamics properties showed that the ESIPT is favorable with a proton transfer equilibrium constant of ~105.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Theoretical chemistry accounts

ISSN

1432-881X

e-ISSN

—

Svazek periodika

135

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

11

Strana od-do

1-11

Kód UT WoS článku

000369976000002

EID výsledku v databázi Scopus

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