Electron Transfer Studies on Conjugated Ferrocenyl-Containing Oligomers

Abstract

1,2-Divinylferrocene (1) and 1,2-diformylferrocene (3) have been converted to ferrocenyl-containing oligomers in good yields using ADMET (acyclic diene metathesis) and HWE (Horner–Wadsworth–Emmons) reaction protocols. The resulting oligomers showed a high uniformity (low dispersity values); however, the poor solubility limits the chain growth and led to low average molecular weights. Within electrochemical measurements (CV) the conjugated materials showed reversible behavior that was stable during multicyclic experiments. Coupled electrochemical and spectroscopic studies confirmed electron transfer interactions between the ferrocenyl units through the oligomeric chains.

Ferrocenyl–triazole complexes and their use in heavy metal cation sensing

“…Electrochemical measurements were performed using 1.0 mmol L −1 solutions of the analytes and [N n Bu 4 ][B(C 6 F 5 ) 4 ] as the supporting electrolyte in anhydrous dichloromethane at 25 °C. 32,33,38,54 The instrumentation consisted of a Radiometer Gamry interface 1010E workstation interfaced with a personal computer. The measurement cell comprised three electrodes: a Pt auxiliary electrode, a glassy carbon working electrode, and a Ag/Ag + (0.01 mol L −1 AgNO 3 ) reference electrode.…”

“…The electrochemical behavior of 3, 6, 7, and 9 was investigated by cyclic voltammetry (CV) using an anhydrous dichloromethane solution of [N n Bu 4 ][B(C 6 F 5 ) 4 ] (0.1 mol L −1 ) as a supporting electrolyte. 32,33,38,[54][55][56]59,101 The electrochemical measurements were conducted at 25 °C under an argon atmosphere and referenced against the potential of the FcH/FcH + redox couple. In all compounds, reversible and well-dened redox events were observed, as illustrated in Fig.…”

“…102 The large DE p value of 176 mV for 3 suggests that three individual reversible one-electron processes exist in a close potential range, indicating a certain degree of electrostatic interaction between the Fc/Fc + moieties. 33,[103][104][105][106] The cyclic voltammetry (CV) data for compounds 6 and 7 revealed the presence of two distinct reversible one-electron processes superimposed on each other (DE p = 66 mV for 6, 65 mV for 7). This suggests the absence of electronic and electrostatic interactions between Fc/Fc + , as illustrated in Fig.…”

“…[24][25][26][27][28] The unique redox activity of ferrocene and some of its derivatives have raised their potential as chemo-sensing materials. [29][30][31][32][33] In addition, heterocyclic compounds such as oxazolines, imidazoles, and triazoles have proven to be efficient recognition units for metal cation detection. [34][35][36][37][38][39] Therefore, ferrocenes are considered invaluable templates as redoxmoieties and in combination with a triazole-heterocyclic derivative can be expected to offer a greater surface area available for the deposition of specic analytes as well as an enhancement in the electron-transfer processes, and consequently, such compounds should stimulate the modied electrodes to behave as multiple signaling molecular selective chemo-sensors for metal cations.…”