An Investigation into the Synthesis of a Four-Armed Diamino Swallowtail

Barnett, Christopher Carter (2015) An Investigation into the Synthesis of a Four-Armed Diamino Swallowtail. Undergraduate thesis, under the direction of Daniell Mattern from Chemistry and Biochemistry, The University of Mississippi.

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Abstract

Perylenebisimides (PBIs) complex with quadruplex DNA and may influence the formation of telomeres. PBIs with amine groups are ionized at neutral pH and therefore soluble in water [1]. Swallowtails are long alkyl chains usually attached to PBIs to inhibit self-aggregation by pi-stacking [2]. Past attempts to create a PBI with swallowtails containing extra nitrogens were unsuccessful due to purification issues and methylene connectors. The purpose of this research is to investigate the synthesis of a diamino swallowtail with a methine connector. The first step is to create 1,3-bis(dibenzylamino)propan-2-one by way of an SN2 substitution reaction using 1,3-dichloroacetone and dibenzylamine [3]. The product was created using the Finkelstein reaction along with a second SN2 substitution reaction [4]. The next step is the creation of an oxime to later be reduced into an amine [5]. Due to lack of time, the creation of the oxime was the furthest step reached. Nonetheless, the trials of this research give valuable insight into the possibility of creating the targeted swallowtails. If ultimately successful, these swallowtails could provide more insight into future research regarding PBI binding to G-quadruplex DNA.

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