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Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases.


ABSTRACT: A new series of ten examples of Schiff bases, namely (E)-2-(((2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)imino)methyl)phenols 3, was easily synthesized with yields of up to 91% from the reactions involving a series of 2-(R-substituted) 6-amino-4-(trifluoromethyl)quinolines 1 and 4(5)-R1-substituted salicylaldehydes 2 - in which alkyl/aryl/heteroaryl for 2-R-substituents are Me, Ph, 4-MeC6H4, 4-FC6H4, 4-NO2C6H4, and 2-furyl, and R1-substituents are 5-NEt2, 5-OCH3, 4-Br, and 4-NO2. Complementarily, the Schiff bases showed low to good quantum fluorescence yield values in CHCl3f = 0.12-0.80), DMSO (Φf = 0.20-0.75) and MeOH (Φf = 0.13-0.85). Higher values of Stokes shifts (SS) were observed in more polar solvents (DMSO; 65-150 nm and MeOH; 65-130 nm) than in CHCl3 (59-85 nm). Compounds 3 presented good stability under white-LED irradiation conditions and moderate ROS generation properties were observed.

SUBMITTER: Rocha IO 

PROVIDER: S-EPMC8649202 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases.

Rocha Inaiá O IO   Kappenberg Yuri G YG   Rosa Wilian C WC   Frizzo Clarissa P CP   Zanatta Nilo N   Martins Marcos A P MAP   Tisoco Isadora I   Iglesias Bernardo A BA   Bonacorso Helio G HG  

Beilstein journal of organic chemistry 20211201


A new series of ten examples of Schiff bases, namely (<i>E</i>)-2-(((2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)imino)methyl)phenols <b>3</b>, was easily synthesized with yields of up to 91% from the reactions involving a series of 2-(R-substituted) 6-amino-4-(trifluoromethyl)quinolines <b>1</b> and 4(5)-R<sup>1</sup>-substituted salicylaldehydes <b>2</b> - in which alkyl/aryl/heteroaryl for 2-R-substituents are Me, Ph, 4-MeC<sub>6</sub>H<sub>4</sub>, 4-FC<sub>6</sub>H<sub>4</sub>  ...[more]

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