Syntheses and Characterization of Ferrocenophanes

Marwan Talib Joudah


Metallocenophanes are divided into two categories, monomolecular metallocenophanes and bimolecular metallocenophanes. This project focused on monomolecular metallocenophanes, in this case where a carbon-based bridge links the two cyclopentadienyl rings of a metallocene. Previous metallocenophanes were prepared by harsh methods and only work to form ferrocenophanes. Therefore, a new method was utilized to synthesize ferrocenophanes that should allow Co, Cr, Mn, Ni, V derivatives to be prepared. This thesis reports the syntheses of four molecules, 1,4-bis(tetramethylcyclopentadienyl)butane, 1,5-bis(tetramethylcyclo-pentadienyl)- pentane, 1,4-bis(cyclopentadienyl)butane, and 1,5-bis(cyclopentadienyl)pentane by utilizing two different methods in 71%, 69%, 98%, and 90% yields, respectively. These four molecules were deprotonated by BuLi, and ultimately reacted with FeCl2•1.5(THF) to obtain [4]octamethylferrocenophane (50%), [5]octamethylferrocenophane (54%), [4]ferrocenophane (34%), and [5]ferrocenophane (28%). The identities of the ferrocenophanes were verified by 1H NMR spectroscopy.