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

  1. Inaiá O. Rocha,
  2. Yuri G. Kappenberg,
  3. Wilian C. Rosa,
  4. Clarissa P. Frizzo,
  5. Nilo ZanattaORCID Logo,
  6. Marcos A. P. Martins,
  7. Isadora Tisoco,
  8. Bernardo A. IglesiasORCID Logo and
  9. Helio G. BonacorsoORCID Logo

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

Beilstein Arch. 2021, 202160. https://doi.org/10.3762/bxiv.2021.60.v1

Published 23 Aug 2021

  • Preprint

Abstract

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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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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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