Week 3: Rerunning reactions from Week 2 and finalizing synthesis of the diketopiperazine

The elimination, isomerization, and Diels Alder reaction from last week did not progress as expected. After workup, 1H NMR analysis showed many different impurities with very little product formed. This could be attributed to remaining impurities in my starting material, resulting from ineffective purification of previous reactions.

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Week 2: Continuation of the [2.2.2] monomer synthesis

This week, I continued my synthesis of the [2.2.2] monomer. 1H NMR analysis of the Aldol reaction from last week confirmed that product 1 formed (see Scheme 1). However, unknown impurities were also present. Therefore, after running various Thin-Layer Chromatography (TLC) plates in multiple solvents, I discovered that I needed to purify the mixture via flash column chromatography on silica gel (5% to 40% EtOAc in hexanes). To do this, I used the lab Biotage which was a very convenient way to perform this purification – this bypassed the tedious work of manually collecting individual fractions.

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Week 1: Aldol Reaction of DKP and Phenylacetaldehyde

This past week in lab, I have continued my synthesis of the [2.2.2] monomer. Specifically, I carried out an aldol reaction with Diketopiperazine (DKP) 1 and phenylacetaldehyde (Scheme 1).

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Synthesis and properties of a [2.2.2]-diazabicyclic polymer

Polymers represent a general class of molecules consisting of many repeated units, or monomers. Traditionally, polymers consist of hydrocarbon monomers and can vary drastically in complexity and functionality. Due to their high molecular weight and chain-like structure, polymers have unique properties that differ significantly from their monomer counterparts, including durability and malleability. For this reason, polymers are used in many everyday products.

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