Controlling the Physical and Electrochemical Properties of Arylamines Through the Use of Simple Silyl Ethers: Liquid, Waxy and Glassy Arylamines

The effect of silyl ether substitution on the physical and electrochemical properties of single and two-nitrogen centered arylamines was explored. It was found that this substitution can significantly lower the Tg and suppress crystallization of these compounds. This resulted in arylamines that were isolated as liquids, waxes, glasses, and in some cases crystalline solids at ambient conditions. Additionally, these silyl ether groups were found to be relatively strong electron donating groups with similar donating potentials to the well known methyl ether group. It is concluded that silyl ether substitution is a synthetic handle to greatly alter the physical properties of arylamines without substantially changing their basic electronic properties.