Studies On Synthesis And Properties Of Novel Ferrocenyl Bisamide Receptors

Supramolecular optical and electrochemical recognition is an area of increasing interest, which focuses on the development of efficient optical- and redox-active receptors. It is greatly significant to both supramolecular chemistry and materials science. The optical- and redox-active receptors are widely used in the fields of ion transport, molecular switch, electrochemical molecular devices, chemical sensors, and so on. Therefore, a study on synthesis, characterization and properties of novel ferrocenyl bisamide receptors was carried out. The main results are as follows:1. Recent research progress of ferrocene-based bisamide receptors, involving molecular design, chemical synthesis and their applications in supramolecular recognition and sensing properties, was briefly reviewed.2. A total of seventeen novel ferrocene-based receptors with one bisamide arm, R1-R11, or two bisamide arm, R12-R17, were firstly synthesized via single and double Ugi four-component reaction from ferrocene carboxylic acid or ferrocene-1,1’-dicarboxylic acid, respectively. Their chemical structures were fully characterized by IR, 1H NMR and HR-MS spectroscopies, as well as for eleven such receptors being determined by X-ray diffraction techniques.3. The recognition and sensing properties of ferrocenyl bisamide receptors prepared, R1-R17, were evaluated by cyclic voltammetry, UV-vis and fluorescence titration techniques. It was found that double-armed ferrocenyl bisamide receptors show better selectivity towards Er3+, Eu3+, Ca2+ and Mg2+ cations than corresponding single-armed ferrocenyl bisamide receptors. In particular, both receptors, R1-R17, show a high selectivity for UV sensing of Er3+, Eu3+, Fe3+ and Cu2+ cations. However, receptors R11 and R17 bearing one anthryl and two anthryl groups, respctively, exhibit a good selectivity for fluorescent sensing of Cu2+ cation.This work has provided a simple and efficient synthesis of novel ferrocenyl bisamide receptors via single and double Ugi four-component reactions and is important for the development of novel optical- and redox-active receptors.