Electrochemical Recognition of Aromatic Species with Ferrocenylated 1,3,5-Triazine- or 1,3,5-Triphenylbenzene-Containing Highly Organized Molecules.

Two ferrocenylated organized molecules comprising 1,3,5-triphenylbenzene (Fc-1) or 2,4,6-triphenyl-1,3,5-triazine skeletons (Fc-2) were used for the first time as receptor layers for the electrochemical recognition of polycyclic aromatic hydrocarbons. While our group recently reported the synthesis of Fc-1, herein the facile synthesis of its 2,4,6-triphenyl-1,3,5-triazine-containing structural analog (Fc-2) is presented. Although the synthesis of Fc-2 was found to be challenging, we achieved a very high yield (89 %) under mild conditions using an acid-catalyzed imine-bond formation reaction in 1,4-dioxane:toluene solvent system. Title compounds were comprehensively characterized with various analytical techniques, including spectroscopic (NMR, FT-IR, FT-Raman spectroscopy) methods, high-resolution mass spectrometry (HRMS), microscopic (SEM) and electrochemical (CV) analyses. Fc-1 and Fc-2 were also used for the construction of the first-of-a-kind recognition layers (electrochemical sensors) dedicated to the recognition of polycyclic aromatic hydrocarbons. Fully constructed innovative sensors enabled the efficient recognition of analytes since the limit of detection (LOD) values were not higher than 2.9 μM. Comparative studies between the working parameters of electrochemical sensors comprising Fc-1 or Fc-2 were also included in this work.