Star‐Shaped Ferrocene‐Based 1,4‐Disubstituted‐1,2,3‐Triazole Derivatives: Synthesis, Characterization, and Investigation of Linear Optical and Electrochemical Properties

Abstract

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.

A decacationic ferrocene-based metallostar

“…6 In many molecular stars the metallocene unit is located in the outskirts of the molecule [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] despite its C 5 symmetry rendering it as an ideal core building block. Examples of ferrocene centered metallostars are rare 23,24 probably due to the synthetic difficulties associated with the poly-or perfunctionalization of ferrocene. 25 In 2021 we reported a simple perfunctionalization approach by treatment of ferrocene with mercury(II) carboxylates to obtain FeC 10 (HgX) 10 (X = O 2 CC 3 H 7 , O 2 CCF 3 , O 2 CCCl 3 ) in multigram scale.…”

“…6 In many molecular stars the metallocene unit is located in the outskirts of the molecule 7–22 despite its C 5 symmetry rendering it as an ideal core building block. Examples of ferrocene centered metallostars are rare 23,24 probably due to the synthetic difficulties associated with the poly- or perfunctionalization of ferrocene. 25…”

Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles

“…The former method for the synthesis of 1,2,3-triazole rings was the thermal condition at high temperatures in general through the coupling reaction between alkynes and organic azides to obtain a mixture of 1,4-and 1,5-disubstituted-1,2,3-triazoles [4]. Moreover, during recent decades CuAAC has developed as a unique alternative and received much consideration due to its exclusive regioselectivity, extensive substrate scope, mild and green reaction conditions, and simple purification which have made it the method of choice for making the most stable connections by means of 1,4-disubstituted-1,2,3-triazoles since its discovery [5][6][7].…”

A Decacationic Ferrocene-Based Metallostar

“…[6] In many molecular stars the metallocene unit is located in the outskirts of the molecule [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] despite its C5 symmetry rendering it as an ideal core building block. Examples of ferrocene centered metallostars are rare [23,24] probably due to the synthetic difficulties associated with the poly-or perfunctionalization of ferrocene. [25] In 2021 we reported a simple perfunctionalization approach by treatment of ferrocene with mercury(II) carboxylates to obtain FeC10(HgX)10 (X = O2CC3H7, O2CCF3, O2CCCl3) in multigram scale.…”