Chemistry Scholarships

Synthesis of Molecular Butterflies and Pinwheels.

This project involves a dynamic collaboration between organic synthetic chemistry and electrochemistry.

In the first part heptahelicene (1, shown above) will be prepared in several steps from phenanthrene-3 carbaldehyde, key reactions being a Wittig coupling followed by photo-isomerisation.  Once prepared 1b will be subjected to a series of 2,4 or more electron reductions or oxidations.  Cyclic voltammetry studies on any intermediates will be carried out as well as the isolation and crystallization of metal salts from any of the reduced an/or oxidized products. It is anticipated that these molecules will be able to be electrochemically and/or chemically  reduced and possibly  oxidized to give a series of related compounds, but with different electronic configurations. If possible, the reduced and oxidized  derivatives will  be characterized as solids materials or if this is not possible, characterization in solution will be attempted by EPR, NMR,electronic spectra  and other methods to establish the location of the electrons, structural changes induced by change in electron numbers and reactivity changes induced by change in the  redox levels. Particularly when an odd number of electrons are present, dynamic fluxional properties are anticipated, which may produce compounds with novel properties.