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

Submitting author affiliation:
Federal University of Santa Maria - UFSM, Santa Maria, Brazil

Beilstein Arch. 2021, 202160.

Published 23 Aug 2021



A new series of ten examples of (E)-2-(((2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)imino)methyl)phenols (Schiff bases), was easy synthesized at yields up to 91% from the reactions involving a series of 2-(R-substituted) 6-amino-4-(trifluoromethyl)quinolines and 4(5)-R1-substituted salicylaldehydes – 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 both 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). Also, compounds 3 confirmed to present good stability under white-LED irradiation conditions and moderate ROS generation properties were observed.

Keywords: Schiff base, quinoline, photophysical properties, photostability, ROS generation.

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Rocha, I. O.; Kappenberg, Y. G.; Rosa, W. C.; Frizzo, C. P.; Zanatta, N.; Martins, M. A. P.; Tisoco, I.; Iglesias, B. A.; Bonacorso, H. G. Beilstein Arch. 2021, 202160. doi:10.3762/bxiv.2021.60.v1

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