Structure–property relationships in para-substituted nitrobenzofurazans: electrochemical, optical, and theoretical analysis

In this work, we seek to understand and to quantify the structure–property relationships of chlorine, methoxy and phenoxy para-substituted nitrobenzofurazans (NBDs). Optical and electrochemical properties of studied materials were explored using UV–Vis spectroscopy and cyclic voltammetry (CV), respe...

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Bibliographic Details
Published inChemical papers Vol. 76; no. 7; pp. 4059 - 4080
Main Authors Raissi, Hanen, Chérif, Imen, Aribi, Imen, Ayachi, Hajer, Haj Said, Ayoub, Ayachi, Sahbi, Boubaker, Taoufik
Format Journal Article
LanguageEnglish
Published Warsaw Versita 01.07.2022
Springer Nature B.V
Subjects
Biochemistry
Biotechnology
Charge transfer
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chlorine
Electrochemical analysis
Energy bands
Energy gap
Industrial Chemistry/Chemical Engineering
Materials Science
Medicinal Chemistry
Optical properties
Original Paper
Spectrum analysis
Substitutes
Cyclic voltammetry
Intra-molecular charge transfer (ICT)
DFT
RDG
Optical properties
Nitrobenzofurazan
Structure–property relationships
ELF
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Summary:In this work, we seek to understand and to quantify the structure–property relationships of chlorine, methoxy and phenoxy para-substituted nitrobenzofurazans (NBDs). Optical and electrochemical properties of studied materials were explored using UV–Vis spectroscopy and cyclic voltammetry (CV), respectively. Through an extrapolation of the linear trend observed in the UV–Vis spectra, the estimated energy band gaps for chlorine, methoxy and phenoxy para-substituted nitrobenzofurazans (NBDs) are 3.22, 2.89 and 2.94 eV, respectively. The electrochemical energy gaps deduced from the CV measurements are 3.34 eV (NBD-Cl), 3.00 eV (NBD-OCH 3 ) and 3.01 eV (NBD-OC 6 H 5 ). The almost complete agreement between the values determined by the two independent experimental methods is remarkable. In addition, the DFT computed band gap energies are closer to the experimental values. Further, the DFT and its extension of TD-DFT methods combined with several topological analyses have been used to understand the nature and the intra-molecular charge transfer (ICT) abilities within the studied molecules.
ISSN:0366-6352
1336-9075
2585-7290
DOI:10.1007/s11696-022-02150-y