新型三氟甲基化喹啉-苯酚席夫碱的光物理、光稳定性及活性氧生成特性
Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases.
作者信息
Rocha Inaiá O, Kappenberg Yuri G, Rosa Wilian C, Frizzo Clarissa P, Zanatta Nilo, Martins Marcos A P, Tisoco Isadora, Iglesias Bernardo A, Bonacorso Helio G
机构信息
1Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97105-900, Brazil.
Laboratório de Bioinorgânica e Materiais Porfirínicos, Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97105-900, Brazil.
出版信息
Beilstein J Org Chem. 2021 Dec 1;17:2799-2811. doi: 10.3762/bjoc.17.191. eCollection 2021.
A new series of ten examples of Schiff bases, namely ()-2-(((2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)imino)methyl)phenols , was easily synthesized with yields of up to 91% from the reactions involving a series of 2-(R-substituted) 6-amino-4-(trifluoromethyl)quinolines and 4(5)-R-substituted salicylaldehydes - in which alkyl/aryl/heteroaryl for 2-R-substituents are Me, Ph, 4-MeCH, 4-FCH, 4-NOCH, and 2-furyl, and R-substituents are 5-NEt, 5-OCH, 4-Br, and 4-NO. Complementarily, the Schiff bases showed low to good quantum fluorescence yield values in CHCl (Φ = 0.12-0.80), DMSO (Φ = 0.20-0.75) and MeOH (Φ = 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 CHCl (59-85 nm). Compounds presented good stability under white-LED irradiation conditions and moderate ROS generation properties were observed.
一系列新的十个席夫碱实例，即()-2-(((2-烷基(芳基/杂芳基)-4-(三氟甲基)喹啉-6-基)亚氨基)甲基)苯酚，通过一系列2-(R-取代)6-氨基-4-(三氟甲基)喹啉与4(5)-R-取代水杨醛的反应轻松合成，产率高达91%。其中，2-R-取代基的烷基/芳基/杂芳基为甲基、苯基、4-甲基苄基、4-氟苄基、4-硝基苄基和2-呋喃基，R-取代基为5-二乙氨基、5-甲氧基、4-溴和4-硝基。此外，席夫碱在氯仿(Φ = 0.12 - 0.80)、二甲基亚砜(Φ = 0.20 - 0.75)和甲醇(Φ = 0.13 - 0.85)中显示出低到良好的量子荧光产率值。在极性更强的溶剂(二甲基亚砜；65 - 150纳米和甲醇；65 - 130纳米)中观察到的斯托克斯位移(SS)值比在氯仿(59 - 85纳米)中更高。化合物在白色发光二极管照射条件下表现出良好的稳定性，并观察到适度的活性氧生成特性。
Zotero 插件