Pyrenehexanoic Acid Synthesis Lab Report

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1-pyrenehexanoic acid was used as the 5-carbon linker and fluorescent component of the target molecule "PYRET-5". This molecule was purchased pure along with the sugar Trehalose, the molecule to which the pyrene was to be attached. Other reactants and solvents include HATU, HBTU, N, N-Diisopropylethylamine (DIPEA), sodium azide, Dimethylformamide (DMF), and Diphenyl phosphoryl chloride and were bought pure or used as received. All reactions were run at room temperature (298.15 K) and standard pressure unless otherwise noted.

The routine lab equipment included a rotary evaporator (evaporating solvents off by lowering boiling point through pressure and temperature changes), analytical balances measuring to one tenth of a milligram, and a lyophilizer (freeze-dryer).

Synthesizing "PYRET-5" molecules

"PYRET-5" (refer to Scheme 1 for structure) was the target molecule to be synthesized by replacing one of the –OH groups with 1-pyrenehexanoic which would be connected by either an ester or an amide group. Both compounds, the ester and the amide, were synthesized with the pyrene as the limiting
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Following TLC, the sample was evaporated with the Rotavap® and then extracted using 4:1 1-butanol and ethyl acetate as the organic layer and water. The sample failed to dissolve, so the organic layer was decanted off, and dichloromethane was used instead. The bottom-layer (dichloromethane and sample) was run through the Rotavap® and the sample residue that was left was reacted with 1-pyrenehexanoic acid. The second step of forming the amide also required TLC, and was done using the same reagents, ethyl acetate and water. The spots, however, on the plate could not be differentiated visually, and thus the reaction may not have run to completion. Mass spectrometry was used instead, and it was determined that the reaction had failed by producing a

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