Abstract:
Some ferrocenyl amides were synthesized by the solution phase condensation reaction of
4-ferrocenyl benzoyl chloride and 4-ferrocenyl aniline with organic amine and acid
chloride derivatives respectively. A series of semi aromatic amine derivatives with
variable alkyl chain at one end was prepared in a three step process which was
condensed with 4-ferrocenyl benzoyl chloride resulting in the formation of ferrocene
derivatives with two amide bonds. Another series with a single amide bond was prepared
by the condensation of 4-ferrocenyl aniline with n-alkyl acid chloride derivatives of
different chain length. The third series of ferrocenyl amides was synthesized by the
reaction of 4-alkoxy benzoyl chloride and 4-ferrocenyl aniline to get seven compounds
with variable alkoxy chain. The fourth and final series was prepared by using 4-(4-
alkoxy phenyl) benzoyl chloride derivative to condense with 4-ferrocenyl aniline and
five products bearing different alkoxy end groups were obtained. All the synthesized
compounds were characterized by their physical properties, elemental analysis, FTIR and
1
H/ 13 CNMR spectroscopic techniques for the structure elucidation. The crystals of some
organic intermediates were also developed and studied for the single crystal XRD
structural factors. A strong intermolecular H-bonding was confirmed for the secondary
amide groups present within all the molecules of the intermediates and final products by
spectroscopic and XRD techniques. These secondary types of forces are pre-requisite for
a compound to interact with the bio molecules such as DNA by developing some
intermolecular forces between the two. Therefore, the synthesized nitroaromatic
compounds and their amine derivatives along with ferrocenyl amides were studied for
the DNA-binding properties by using UV visible spectroscopic and cyclic voltammetric
techniques. The DNA-interactional behaviour of organic intermediates was also
supported by the docking studies leading to the conformation of bonding modes that are
accessible. Ferrocenyl amides and nitroaromatic compounds were investigated for their
electrochemical properties and the redox mechanism involved for the both was suggested
using cyclic voltammetric methods. The melting point behavior of the synthesized
materials was also depictive of their mesomorphic nature, so the selected compounds
were studied for the metallomesogenic properties using DSC and POM techniques. The
phase transition temperatures and the heat changes associated with different transitions
were evaluated for the thermodynamic behavior of the materials and texture of the
iiiAbstract
mesophases were studied by POM at different temperatures. The thermotropic liquid
crystalline nature of the synthesized compounds was found to have some relationship
with the structure of molecules which was further evaluated by the theoretical
calculations of the rigid and flexible part lengths of molecules by using PM6 method.
The effect of alkyl and alkoxy chain lengths on the electrochemical, DNA-binding and
liquid crystalline properties were studied in detail and found to influence the properties
in following order; liquid crystalline > electrochemical > DNA-binding properties. In
fact, it has no effect on DNA-binding strength as alkyl chain is not being actively
involved in the binding process.