Attempted synthesis of 1,2-diamino-4,5-bis(dodecoxy)benzene as a precursor to new metallomesogens

CHED 1181

Amber Bisch, bischa@washjeff.edu, Brenda A. Frazier, and Steven M. Malinak, smalinak@washjeff.edu. Department of Chemistry, Washington and Jefferson College, 50 South Lincoln Street, Box #149, Washington, PA 15301
Liquid crystals, also known as mesogens, exist in an intermediate phase between that of an ordered solid and a flowing liquid. Metallomesogens are liquid crystals that contain metal atoms. Surface area is important in the interaction between two molecules in that large surface areas allow for strong interactions in the liquid state leading to the formation of liquid crystalline phases. The ultimate goal of this investigation is to synthesize and examine the properties of new discotic metallomesogens consisting of one metal atom (see figure). Derivatives of the compound were synthesized with n=11, m=0, and M=Ni2+or Cu2+. Early investigations of the thermal properties of the molecule suggest liquid crystalline behavior. The enduring focus of this project is to synthesize new metallomesogens by varying the values of m. To accomplish this goal, means of obtaining 1,2-diamino-4,5-bis(dodecoxy)benzene as a precursor to the metallated ligand are currently being explored.