FERROCENYL AMIDES, PROMISING MATERIALS FOR CERTAIN POTENTIAL APPLICATIONS

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.