1999 Summer Research Fellow

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Jeremy Nelson

Jeremy just graduated from Carleton College with a B.S. in Chemistry.

Synthesis of Tetra(carboxy)TTF and Tris(4-pyridyl)benzene for the Purpose of Forming Redox-active Heterocrystals
Jeremy Nelson
Carleton College

Michael D. Ward
Department of Chemical Engineering and Materials Science, University of Minnesota

The redox active tetra(carboxy)tetrathiafulvane was successfully synthesized and isolated using a coupling reaction between 4,5-dicarbomethoxy-1,3-dithiole-2-thione followed by a basification reaction using potassium hydroxide to convert the tetrathiafulvalene (TTF) tetra(methyl ester) into the TTF tetra(carboxy) acid. 1,3,5-tris(4-pyridyl)benzene was also synthesized using a multi-step procedure involving the formation of a tri(methyl)tinpyridine reagent which was then reacted with tribromobenzene. Column chromatography on an alumina gel column was then attempted in order to isolate the desired final product. This purification procedure proved unreliable, although some pure product was isolated. The procedure used to synthesize 1,3,5-tris(4-pyridyl)benzene should prove to be a general method capable of yielding numerous poly(4-pyridyl)-substituted benzenes. Efforts were also directed towards the synthesis of di(carboxy)TTF and ferrocinedialdehyde.