Deoxyribonucleic Acid (DNA) is the fundamental building block for protein synthesis in living organisms. Because DNA reproduction is heightened in rapidly growing cells, cancerous cells can in theory be specifically targeted over healthy cells using DNA intercalators. We have designed four carboline homodimers that are stereoisomers of one another. The proposed carboline homodimers (Figure 1) possess seven consecutive fused rings. Specifically, a central diketopiperazine unit connects two identical heteroaromatic cores. Due to the extended aromatic framework of the homodimers, we suspect that these compounds will function as doubly lethal DNA intercalators. Progress towards the synthesis and characterization of these homodimers will be presented. We will also discuss UV-Vis and fluorescence studies detailing the intercalating abilities of selected homodimers.