Title

Synthesis of 1'-ethyne-1-ferrocenecarboxylic Acid

Authors

Sean O'Connor

Document Type

Article

Publication Date

2011

Abstract

1'-ethyne-1-ferrocenecarboxylic acid is a compound which will serve as a linker molecule between DNA and a gold micro array. Its unique electrochemical properties allow quantitative data to be collected regarding the electrical conductivities of many samples of DNA, and their respective binding proteins simultaneously. The original synthesis began by deprotonating ferrocene with t-butyl lithium, and reacting it with tributyltin chloride to create a mixture of mono- and bis-substituted stannyl ferrocene. These were separated on a silica column, and the bis-substituted product was reacted with Iodine to form 1,1'-diiodoferrocene. The following reaction, which attempted a nucleophilic attack on carbon dioxide, was hindered due to the presence of various tin derivatives. An alternate synthesis of 1,1'-diiodoferrocene, involving a halomecuriferrocene, yields the product without Tin derivatives.

Advisor

Michael Hill

Department

chemistry

Support

Howard Hughes Medical Institute Undergraduate Science Education Grant



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