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

Beilstein Journal of Organic Chemistry

Clarissa P. Frizzo¹  Isadora Tisoco¹  Yuri G. Kappenberg¹  Inaiá O. Rocha¹  Nilo Zanatta¹  Marcos A. P. Martins¹  Wilian C. Rosa¹  Bernardo A. Iglesias¹  Helio G. Bonacorso¹ 

[1] 1Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97105-900, Brazil;

关键词: photophysical properties;    photostability;    quinoline;    ros generation;    schiff base;   

DOI  :  10.3762/bjoc.17.191

来源: DOAJ

【 摘 要 】

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 CHCl3 (Φf = 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.

【 授权许可】

Unknown