Approaches to organic metals

ORGN 404

Zachariah A. Page, pageza06@juniata.edu, Mohammad A. Khoshnevisan, khoshma05@juniata.edu, and I. David Reingold, reingold@juniata.edu. Department of Chemistry, Juniata College, 1700 Moore St., Campus Box 102A, Huntingdon, PA 16652
Polycyclic Aromatic Compounds (PACs) have potential uses in electronics due to the extended pi system and pi stacking. Polyhydroxykekulene and zig-zag polyacenol are PACs that have the potential to be used as OLEDs, non-linear optics, photovoltaic cells, field effect transistors and other electronics. The synthesis of these PACs can be theoretically accomplished through multiple tandem Michael-Dieckmann reactions using 4,4-dimethoxy-cyclohexa-2,5-dienone (I); 4,4-dimethoxy-5-carbomethoxymethyl-2-cyclohexenone (II); and 4,4-dimethoxy-3,5-bis(carbomethoxymethyl)-cyclohexanone (III). We can show the feasibility of synthesizing polyhydroxokekulene through the synthesis of perhydrophenanthrene-1,5,10-trione (IV) and phenanthrene-1,5,10-triol. Syntheses of compounds I–IV will be reported.