{"title":"3,5-双((2-羟基亚苄基)氨基)-N-(2-羟基苯基)苯甲酰胺和 Zn(II) 复合物的合成与表征:色度、荧光和 DPPH 自由基清除行为的研究","authors":"Özlem Güngör","doi":"10.1016/j.ica.2024.122410","DOIUrl":null,"url":null,"abstract":"<div><div>Novel amido-Schiff base 3,5-bis((2-hydroxybenzylidene)amino)-<em>N</em>-(2-hydroxyphenyl)benzamide (<strong>2a</strong>) has been obtained by the reaction of Schiff base <strong>1a</strong> with 2-hydroxyaniline in the presence of coupling agent <em>N,N′-</em>dicyclohexylcarbodiimide. Schiff base (<strong>1a</strong>) which serves as the starting compound in amide synthesis was produced from the condensation of 3,5-diaminobenzoic acid with salicylaldehyde in a 1:2 mol ratio. Tetrahedral geometry with 1:1 [M:L] stoichiometry Zn(II) complex (<strong>3a</strong>) was newly synthesized by the complexation reaction of ligand <strong>2a</strong> with zinc(II) nitrate. <strong>1a</strong> and <strong>2a</strong> displayed a broad emission band at λ<sub>em</sub> = 456 and 472 nm with a blue fluorescent in pure DMSO, while <strong>3a</strong> emitted a strong greenish-blue fluorescent with the λ<sub>em</sub> = 485 nm (λ<sub>exc</sub> = 365 nm). The fluorescence efficiency of <strong>1a</strong> was poor compared to the others. The λ<sub>em</sub> in aqueous DMSO solution (v/v, 1:1) had ∼8–33 nm red-shift with respect to that of pure solution. The λ<sub>em</sub> gave ∼1–15 nm red-shift with very low emission efficiency in acidic DMSO media. The results suggested that the aggregation caused quenching properties of <strong>1a–3a</strong> in pure, aqueous, and acidic DMSO system with a 50 % water fraction. The fluorescence of the compounds appeared to be visibly very bright in basic DMSO media. All the compounds were also screened for antioxidant activity using UV–Vis spectroscopy. They were found to be not effective DPPH radical scavengers in DMSO.</div></div>","PeriodicalId":13599,"journal":{"name":"Inorganica Chimica Acta","volume":"574 ","pages":"Article 122410"},"PeriodicalIF":2.7000,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and characterization of 3,5-bis((2-hydroxybenzylidene)amino)-N-(2-hydroxyphenyl)benzamide and Zn(II) complex: Investigation of chromic, fluorescence and DPPH radical scavenging behaviours\",\"authors\":\"Özlem Güngör\",\"doi\":\"10.1016/j.ica.2024.122410\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Novel amido-Schiff base 3,5-bis((2-hydroxybenzylidene)amino)-<em>N</em>-(2-hydroxyphenyl)benzamide (<strong>2a</strong>) has been obtained by the reaction of Schiff base <strong>1a</strong> with 2-hydroxyaniline in the presence of coupling agent <em>N,N′-</em>dicyclohexylcarbodiimide. Schiff base (<strong>1a</strong>) which serves as the starting compound in amide synthesis was produced from the condensation of 3,5-diaminobenzoic acid with salicylaldehyde in a 1:2 mol ratio. Tetrahedral geometry with 1:1 [M:L] stoichiometry Zn(II) complex (<strong>3a</strong>) was newly synthesized by the complexation reaction of ligand <strong>2a</strong> with zinc(II) nitrate. <strong>1a</strong> and <strong>2a</strong> displayed a broad emission band at λ<sub>em</sub> = 456 and 472 nm with a blue fluorescent in pure DMSO, while <strong>3a</strong> emitted a strong greenish-blue fluorescent with the λ<sub>em</sub> = 485 nm (λ<sub>exc</sub> = 365 nm). The fluorescence efficiency of <strong>1a</strong> was poor compared to the others. The λ<sub>em</sub> in aqueous DMSO solution (v/v, 1:1) had ∼8–33 nm red-shift with respect to that of pure solution. The λ<sub>em</sub> gave ∼1–15 nm red-shift with very low emission efficiency in acidic DMSO media. The results suggested that the aggregation caused quenching properties of <strong>1a–3a</strong> in pure, aqueous, and acidic DMSO system with a 50 % water fraction. The fluorescence of the compounds appeared to be visibly very bright in basic DMSO media. All the compounds were also screened for antioxidant activity using UV–Vis spectroscopy. They were found to be not effective DPPH radical scavengers in DMSO.</div></div>\",\"PeriodicalId\":13599,\"journal\":{\"name\":\"Inorganica Chimica Acta\",\"volume\":\"574 \",\"pages\":\"Article 122410\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-10-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Inorganica Chimica Acta\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0020169324005012\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Inorganica Chimica Acta","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0020169324005012","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Synthesis and characterization of 3,5-bis((2-hydroxybenzylidene)amino)-N-(2-hydroxyphenyl)benzamide and Zn(II) complex: Investigation of chromic, fluorescence and DPPH radical scavenging behaviours
Novel amido-Schiff base 3,5-bis((2-hydroxybenzylidene)amino)-N-(2-hydroxyphenyl)benzamide (2a) has been obtained by the reaction of Schiff base 1a with 2-hydroxyaniline in the presence of coupling agent N,N′-dicyclohexylcarbodiimide. Schiff base (1a) which serves as the starting compound in amide synthesis was produced from the condensation of 3,5-diaminobenzoic acid with salicylaldehyde in a 1:2 mol ratio. Tetrahedral geometry with 1:1 [M:L] stoichiometry Zn(II) complex (3a) was newly synthesized by the complexation reaction of ligand 2a with zinc(II) nitrate. 1a and 2a displayed a broad emission band at λem = 456 and 472 nm with a blue fluorescent in pure DMSO, while 3a emitted a strong greenish-blue fluorescent with the λem = 485 nm (λexc = 365 nm). The fluorescence efficiency of 1a was poor compared to the others. The λem in aqueous DMSO solution (v/v, 1:1) had ∼8–33 nm red-shift with respect to that of pure solution. The λem gave ∼1–15 nm red-shift with very low emission efficiency in acidic DMSO media. The results suggested that the aggregation caused quenching properties of 1a–3a in pure, aqueous, and acidic DMSO system with a 50 % water fraction. The fluorescence of the compounds appeared to be visibly very bright in basic DMSO media. All the compounds were also screened for antioxidant activity using UV–Vis spectroscopy. They were found to be not effective DPPH radical scavengers in DMSO.
期刊介绍:
Inorganica Chimica Acta is an established international forum for all aspects of advanced Inorganic Chemistry. Original papers of high scientific level and interest are published in the form of Articles and Reviews.
Topics covered include:
• chemistry of the main group elements and the d- and f-block metals, including the synthesis, characterization and reactivity of coordination, organometallic, biomimetic, supramolecular coordination compounds, including associated computational studies;
• synthesis, physico-chemical properties, applications of molecule-based nano-scaled clusters and nanomaterials designed using the principles of coordination chemistry, as well as coordination polymers (CPs), metal-organic frameworks (MOFs), metal-organic polyhedra (MPOs);
• reaction mechanisms and physico-chemical investigations computational studies of metalloenzymes and their models;
• applications of inorganic compounds, metallodrugs and molecule-based materials.
Papers composed primarily of structural reports will typically not be considered for publication.