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Star‐Shaped Ferrocene‐Based 1,4‐Disubstituted‐1,2,3‐Triazole Derivatives: Synthesis, Characterization, and Investigation of Linear Optical and Electrochemical Properties
Author(s) -
Rahimpour Keshvar,
TeimuriMofrad Reza
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5943
Subject(s) - chemistry , ferrocene , electrochemistry , cyclic voltammetry , cycloaddition , triazole , ascorbic acid , 1,2,3 triazole , glassy carbon , redox , inorganic chemistry , organic chemistry , electrode , catalysis , food science
In this study, the star‐shaped ferrocene‐based 1,4‐disubstituted‐1,2,3‐triazole derivatives were designed and synthesized via Huisgen reaction. For this purpose, the [3 + 2] cycloaddition reaction between multi‐(4‐azidobutyl) substituted ferrocene derivatives and ethynylferrocene was carried out in the presence of CuSO 4 .5H 2 O as Cu (I) source and ascorbic acid as reluctant for convert the Cu (II) to Cu (I). The optical and electrochemical properties of the final dendrimer‐like ferrocenyl derivatives were evaluated using UV–vis spectroscopy (UV–vis) and cyclic voltammetry (CV) techniques, respectively. The linear relationship between the cathodic and anodic peak currents and the square root of the scan rate was indicated the diffusion‐limited mechanism for the redox process. Furthermore, ferrocene‐based 1,4‐disubstituted‐1,2,3‐triazole derivatives show good electrochemical behavior (the CV and DPV technique) when immobilized on glassy carbon electrode surface using Nafion. In addition, the quantum chemistry study was performed on the synthesized compounds with the DFT approach. The B3LYP/6‐31G(d) method was applied to do TD‐DFT calculations due to its good agreement with experimental data for prediction of UV–Vis spectra.