Synthesis of novel molecular cli̇p based on norbornadiene framework

In this thesis, a novel molecular clip, posses norbornadiene skeleton, was synthesized by the imine condensation reaction of racemic -amino ketone 56. Surprisingly, it was observed that only syn isomer was formed from two isomers (syn and anti) that were likely to occur. The exact structure of the C2v symmetric molecular clip was proved by X-ray analysis and NMR spectroscopy. The molecular clip was subjected to further reaction steps with amino acids such as alanine, threonine and 4-amino benzoic acid, and carboxylic acid functional amide derivatives were obtained. The carboxylic acid groups of imides were deprotonated with NaOH to ensure the water solubility of the clip derivatives. In NMR studies, it was observed that the obtained carboxylate salts self-assembled to form dimers in water. The dilution experiments revealed that the dimerization of salts was concentration-independent.