Synthesis and photochromic properties of some N-phthalimide azo-azomethine dyes. A DFT quantum mechanical calculations on imine-enamine tautomerism and trans-cis photoisomerization

Georgiev, Anton; Stoilova, Ani; Dimov, D; Yordanov, Dancho; Zhivkov, I.; Weiter, Martin

doi:10.1016/j.saa.2018.11.033

Cited by 28 publications

(9 citation statements)

References 30 publications

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“…Azo dyes 3-14 were prepared by coupling reactions of diazonium salts of compounds 1 & 2 with different substituted phenols. FTIR spectral data confirmed the formation of azo dyes 3-10 by the appearance of (OH) stretching bands at (3421-3365) cm -1 and (NH) stretching bands at (3355-3174) cm -1 due to the occurring of a tautomerization process between OH and N=N groups, as explained in equation 1 [20]. Also, FTIR spectral data showed the appearance of (N=N) stretching bands at 1483-1461 cm -1 , while (NH 2 ) stretching bands disappeared from the spectrum.…”

Section: Methodsmentioning

confidence: 52%

Synthesis and Characterization of New Azo Compounds Linked to 1, 8-Naphthalimide and Studying Their Ability as Acid-Base Indicators

Al-Majidi

Al-Khuzaie

2019

eijs

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New Azo compounds containing an 1,8-naphthalimide moiety were synthesized from 1, 8-naphthalic anhydride by a reaction with p-phenylenediamine or benzidine to produce 1,8-naphthalimide derivatives (1 or 2), which were converted to diazonium salt derivatives by using sodium nitrite and acetic acid at 0-5 áµ’C. The diazonium salt was subjected to a coupling reaction with different substituted phenol in alkaline media at 0-5 áµ’c to produce azo compound derivatives (3-14). The New Azo compound derivatives (3-14) were identified by 1H-NMR, 13C-NMR, and FTIR and by measuring characteristic physical properties and specific reactions. Also, the ability of the prepared azo compounds to work as acid-base indicator was investigated, since azo dyes have different and sharp colors in acidic or basic solutions.

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Section: Methodsmentioning

confidence: 52%

Synthesis and Characterization of New Azo Compounds Linked to 1, 8-Naphthalimide and Studying Their Ability as Acid-Base Indicators

Al-Majidi

Al-Khuzaie

2019

eijs

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“…Like the other cyclic imides, phthalimides are characterized by a pair of carbonyls that are bound to the same nitrogen atom (Figure 1) [4]. These compounds have a number of similar characteristics such as hydrophobicity, which assures greater bioavailability and thus greater membrane diffusion capacity [5].…”

Section: Am J Biomed Sci and Resmentioning

confidence: 99%

Therapeutic Potential of Phthalimide Derivatives: A Review

Júnior

Holanda

RodriguesGambôa

et al. 2019

AJBSR

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“…Thus, the development of effective molecular sensors for the detection of metal ions is an evolving field in chemistry due to their simplicity, low cost, sensitive ion-induced spectroscopic and electrochemical changes, easy monitoring of operating conditions, and analysis in real time [ 2 , 3 , 4 ]. Many chemists have focused on the advances in the analysis of azo dyes, which has led to their direct use as chromophoric and metallochromic reagents [ 5 , 6 ], high-performance materials [ 7 , 8 ], photo-sensitizers [ 9 , 10 ], colorants [ 11 , 12 , 13 ], environmental sensors for substrate detection [ 14 , 15 , 16 ] and analytical reagents; they are important in the production of paints because they cover a large range of colors (practically every shade from yellow to black) [ 17 , 18 ]. Azo multifunctional dyes, in addition to the characteristic azo (-N=N-) group [ 19 ], could contain various substituents in aromatic rings or groups involved in complex formation processes, such as azomethine (-CH=N-), that can enhance or hinder their application [ 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Complex Activity and Sensor Potential toward Metal Ions in Environmental Water Samples of N-Phthalimide Azo-Azomethine Dyes

et al. 2021

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Herein, the spectral and electrochemical characterizations of three different substituted N-phthalimide azo-azomethine (NAA) dyes (L) containing an o-hydroxy group and their NAA-M(II) chelates [M(II): Cu, Ni, Co, Pb] were reported by using UV–Vis and fluorescence spectroscopy and potentiometric and voltamperometric techniques. The pK value of the dyes as well as the stoichiometry and stability of the NAA-metal chelates were studied, and the stoichiometry was found to be mostly 1:2 (ML2) with high complex stability constant values. The sensor activity of N-phthalimide azo-azomethine derivatives toward pH and metal ions has been also investigated and tested for indicator application in acid–base analysis and detection of Cu(II) ions in real samples of surface river water using voltamperometric detection. The results showed that one of the ligands possesses the highest electrochemical response upon binding to copper ions and could be successfully used in the analysis of copper in water at a concentration range of the analyte from 3.7 × 10−7 to 5.0 × 10−6 mol L−1, with analytical characteristics of the method being Sr = 1.5%, LOD = 3.58 µg L−1 and LOQ =11.9 µg L−1

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Synthesis and photochromic properties of some N-phthalimide azo-azomethine dyes. A DFT quantum mechanical calculations on imine-enamine tautomerism and trans-cis photoisomerization

Cited by 28 publications

References 30 publications

Synthesis and Characterization of New Azo Compounds Linked to 1, 8-Naphthalimide and Studying Their Ability as Acid-Base Indicators

Synthesis and Characterization of New Azo Compounds Linked to 1, 8-Naphthalimide and Studying Their Ability as Acid-Base Indicators

Therapeutic Potential of Phthalimide Derivatives: A Review

Complex Activity and Sensor Potential toward Metal Ions in Environmental Water Samples of N-Phthalimide Azo-Azomethine Dyes

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