Structure-fluorescence relationships in 2-ary1-5-(2 '-aminophenyl)-4-hydroxy-1,3-thiazoles

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F19%3A39914399" target="_blank" >RIV/00216275:25310/19:39914399 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0022286018309578?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0022286018309578?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2018.08.017" target="_blank" >10.1016/j.molstruc.2018.08.017</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Structure-fluorescence relationships in 2-ary1-5-(2 '-aminophenyl)-4-hydroxy-1,3-thiazoles

Popis výsledku v původním jazyce

Five substituted 2-aryl-4-hydroxy-5-(2&apos;-aminophenyl)-1,3-thiazoles have been studied for their fluorescence properties under neutral and alkaline conditions in solutions of various organic solvents. From comparison with the analogous 2-aryl-4-hydroxy-5-(2&apos;-hydroxyphenyl)-1,3-thiazoles it is clear that both in neutral as well as in the deprotonated state the presence of the 2&apos;-amino group lowers the fluorescence quantum yields (Phi). Introduction of an electron withdrawing groups into the 2-aryl group further decreases Phi. Upon deprotonation of the 4-hydroxy group a large bathochromic shift of the absorption (Delta lambda(A)=100-125 nm) as well as emission (Delta lambda(F)=100-120 nm) bands occurs. An intramolecular hydrogen bond between the amino and hydroxyl groups is obvious. The first absorption band of all studied compounds corresponds to a pi-pi* HOMO-LUMO transition with a CT character. Thiazoles 3b-f and their deprotonated forms 3b(-)-f(-) display fluorescence properties with large Stokes shift (ca 9000 cm(-1) and 6000 cm(-1), respectively) and moderate quantum yields (0.11-0.41), both are connected with the presence of inter and intramolecular hydrogen bonds.

Název v anglickém jazyce

Structure-fluorescence relationships in 2-ary1-5-(2 '-aminophenyl)-4-hydroxy-1,3-thiazoles

Popis výsledku anglicky

Five substituted 2-aryl-4-hydroxy-5-(2&apos;-aminophenyl)-1,3-thiazoles have been studied for their fluorescence properties under neutral and alkaline conditions in solutions of various organic solvents. From comparison with the analogous 2-aryl-4-hydroxy-5-(2&apos;-hydroxyphenyl)-1,3-thiazoles it is clear that both in neutral as well as in the deprotonated state the presence of the 2&apos;-amino group lowers the fluorescence quantum yields (Phi). Introduction of an electron withdrawing groups into the 2-aryl group further decreases Phi. Upon deprotonation of the 4-hydroxy group a large bathochromic shift of the absorption (Delta lambda(A)=100-125 nm) as well as emission (Delta lambda(F)=100-120 nm) bands occurs. An intramolecular hydrogen bond between the amino and hydroxyl groups is obvious. The first absorption band of all studied compounds corresponds to a pi-pi* HOMO-LUMO transition with a CT character. Thiazoles 3b-f and their deprotonated forms 3b(-)-f(-) display fluorescence properties with large Stokes shift (ca 9000 cm(-1) and 6000 cm(-1), respectively) and moderate quantum yields (0.11-0.41), both are connected with the presence of inter and intramolecular hydrogen bonds.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

—

Svazek periodika

1175

Číslo periodika v rámci svazku

January

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

7

Strana od-do

"804–810"

Kód UT WoS článku

000449141100083

EID výsledku v databázi Scopus

2-s2.0-85053113468