Synthetic approaches to molecular motors and conjugated oligomer libraries
Tour, James M.
Doctor of Philosophy
Chapter 1 describes the synthesis of four caltrop-shaped molecules that might be useful as surface-bound electrical field driven molecular motors. The caltrops have a pair of electron donor-accepter arms which form a strong dipole moment. The direction and movement of the dipolar unit could be influenced by an outer electric field. The caltrops also have three benzylic thiols for bonding to a gold surface. Ellipsometry results indicate that monolayers of caltrop molecules form on a gold surface. Chapter 2 and Chapter 3 detail efforts to synthesize libraries of oligo (phenylene vinylene)s (OPVs) using combinatorial synthesis. A series of building blocks for OPVs were synthesized. Model studies were carried out to optimize the reaction strategies and to make OPV tetramers from the building blocks. Chapter 2 describes using the fluorous mixture synthesis (FMS) technology to synthesize a library of OPVs in solution phase. Chapter 3 describes the synthesis of OPVs using solid phase organic synthesis (SPOS). The NMR spectral properties of a group of intermediates frequently encountered in combinatorial synthesis, 1-aryl-3,3-dialkyltriazenes are discussed in Chapter 4.