Synthesis of Molecular Scale Devices with Heteroatomic Functionalities

Synthesis of Molecular Scale Devices with Heteroatomic Functionalities 

Described here are the syntheses of functionalized molecular scale devices which are designed to have nonlinear I(V) responses by adding heterofunctionalities to modulate the n-electron system. Some of the systems 

Compound 71 differs from 70 in that it possesses an acetamide rather than an amine moiety. The Pd/Cu-catalyzed coupling reaction to form 71 proceeded at a faster rate than the coupling to the amine/nitro compound due to the diminished electron donating potential of the acetamide allowing for faster Pd oxidative addition across the aryl bromide bond. The overall net dipole moment of this compound has been calculated to be 2.7 Debye, substantially lower than that for 70.  

85 had limited solubility, it was dehydrated in the presence of ((1 15)3 and EtsN to afford the isonitrile 86.  

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