New Ferrocene Chalcones Derivative's Polymers
Fajardo Tolentino, Johanna
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Polymers represent the largest and versatile class of biomaterials being extensively applied in multiple biomedical applications. This versatility is attributed to the relative ease with which polymers can be designed and prepared with a wide variety of structures and appropriate physical, chemical, surface, and biomimetic properties. Ferrocene polymers have been widely studied because of their many applications. These applications include biocatalysis, biosensing, biofuel cells, films, anticancer agents, biomedical engineering, material sciences, biophysics, and synthetic organic chemistry. However, one of the most explored applications of these ferrocene polymers is based on their unique electrochemical properties. Ferrocene derivatives show different electronic, optical, and redox properties due to their structure and among the possible applications, they can be used to prepare a series of electrochemical labels for the detection of DNA hybridization. In this research the syntheses and characterization of eight new ferrocenyl polymers from ferrocenyl chalcones is discussed. Among the ferrocene derivatives there are two different series by exchanging the relative position of the carbonyl and the double bond attached to ferrocene systems:1-ferrocenyl called Series A ferrocene chalcones and Series B correspond to 3-ferrocenyl chalcones. Each compound was characterized by NMR spectroscopy, FT-IR, melting point determination, UV/Visible Spectroscopy and Cyclic Voltammetry or Osteryoung Square Wave Voltammetry. The synthetic approach for the target compounds follows a route that encompasses a Claisen-Schmidt condensation to obtain the nitro ferrocenyl chalcones, then a chemioselective reduction of the nitro group, followed by the amidation of a 14 phenylamine substrate to synthesize the monomers as the precursors for the polymers after applying a free radical reaction. The synthesis and characterization of six-ferrocenyl chalcones derivatives as precursors for the polymers is discussed in Chapter 2. Among them, two derivatives have not been reported. As discussed in Chapter 2, they were synthesized in good to moderate yields (65–90%). Furthermore, in Chapter 3, the synthesis and characterization of eight novel polymers prepared from the ferrocenyl chalcones derivatives is discussed. The polymers were synthesized by free radical polymerization using azobisisobutyronitrile (AIBN) as initiator, in 39-86% yields. These derivatives were characterized using: 1H NMR, 13C NMR, FT-IR Spectroscopy, Cyclic Voltammetry (CV) and Ultraviolet-Visible Spectroscopy (UV-Vis).