Session: New Reactions & Methodology:

Aluminum is a harmful metal that appears in water systems across Appalachia. It is important for water quality personnel to be able to quickly tell the amount of aluminum present in a water source. The ligand (E)-1-(5-ethynyl-2-hydroxystyryl)napthalen-2-ol will be able to complex aluminum, which causes it to luminesce under fluorescent light. This behavior is ideal for the molecule to be used as an aluminum indicator on sensors in waterways. To make this ligand, two molecules must be synthesized and joined. Presently, one of the two molecules has been successfully prepared by producing three variations of the starting material, 2-hydroxy-1- naphthaldehyde, with different protecting groups for the alcohol. The second molecule is still being synthesized, with completion of protecting the alcohol with a pivalate group and creating the alkyne using the Ohira-Bestmann modification of the Seyferth-Gilbert homologation. Bromination of the alkyne is currently in progress, using NBS and heat. Future actions include adding the triethyl phosphite to the second molecule and then joining it with the first molecule. The last step is a deprotection to yield the desired final product, (E)-1-(5-ethynyl-2-hydroxystyryl)napthalen-2-ol. The major method of purification for this reaction sequence has been column chromatography. Proton NMR has been the primary tool used to confirm formation of the products.

Rachel Minney

Appearances