Tesis
New Ferrocene Chalcones Derivative's Polymers
Autor
Fajardo Tolentino, Johanna
Montes González, Ingrid (Consejera)
Institución
Resumen
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).