FIRST-GENERATION MOLECULAR MOTOR FROM ISOLONCHOCARPIN VIA MCMURRY REACTION

• Main Author: Bongso, Anthony
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/64954
• Institution: Institut Teknologi Bandung

Molecular motors are molecular systems that able to rotate 360o by utilizing the energy of light or heat. The development of molecular motors has been projected to be a pioneer in the field of nano-machinery. Generally, the synthesis of molecular motors requires a long synthesis step, a lot of chemicals, and a long reaction time considering the relatively large size of the molecular motor. In this research, the first-generation molecular motor (2) based on Indonesian's natural compound, namely (-)-isolonchocarpin from Tephrosia vogelii will be synthesized through the McMurry reaction. Isolonchocarpin was chosen due to its relatively planar structure and the presence of a stereogenic center that facilitates the characterization of the rotational movement of the molecular motor. Before the synthesis of the first generation molecular motor, a model compound 1,1'-dimethylstilbene (1) has been synthesized from acetophenone through the McMurry reaction. The selection of acetophenone was based on the similarity of the structure with isolonchocarpin. Brominated isolonchocarpin (3) has also been synthesized as a precursor for first-generation molecular motor variations. The model compound (1) has been successfully synthesized with a yield of 39.22% (E: Z = 4: 1), the first generation molecular motor (2) has been successfully synthesized with a yield of 44.41%, and brominated flavanone (3) has been successfully synthesized with a yield of 31.32%.