Synthesis And Properties Of Anion Receptor Based On Electrochemical Sense

Molecular recognition is an important research area in supramolecular chemistry.The development of anion coordination chemistry is delayed compared with neutralmolecules and cations. It is necessary to construct novel anion receptors. Recently, thesignificant role of anionic species in biology and the environment has led to increasedinvestigation into designing molecules suited to their analytical determination byelectrochemical methods. The anion receptor generally includes two groups, whichare the group that binds anion and the group that expresses the anion binding signal,which connect directly or through a connect arm. Therefore, the design of theinformation reporting groups, the anion binding groups and the connect arm is veryimportant in the study of anion recognition.In this paper, first, by means of cross-coupling and deprotection to obtain2,3-dibutylthiotetrathiafulvaleno [6,7-c]pyrrole 13 from 4,5-dibutylthio-1,3-Dithiole-2-one and N-tosyl-2-thiono-1,3-dithiolo[4,5-c] pyrrole. Under base condition, 13 reactwith formalin(37%) to give N-hydroxymethyl product 14. The target compounds werecharacterized by ¹H NMR, ¹³C NMR, IR, MALDI-TOF-MS and elemental analysis.The coupling behavior of 14 was studied with ¹H NMR in different polar solvents.Secondly, we have designed and synthesized three anion receptors whichcombined with monopyrrole-TTF unit. The target compounds were characterized by¹H NMR, ¹³C NMR, IR, MS(EI). From UV-vis spectra of the complex of targetcompound 14c and F, the intramolecular charge-transfer (CT) absorption band wasobserved clearly. We have studied the binding ability between the receptor 14b, 14cand F^-, AcO^-, H₂PO₄^- through ¹H NMR, UV-vis, and Cyclic voltammetry method. Wefind compound 14c have remarkable electrochemical sensitivity and selectivity towards F^-, which combined with visible colour change. The NMR also exhibits thisresult.