The thesis describes the incorporation of a non-traditional heterocycle into squaraine dyes to redshift the absorbance beyond what is reported in the literature. The first chapter highlights three heterocycles incorporated into the squaraine dyes, indole, quinoline, and perimidine. The main goal is to emphasize the use of other heterocycles other than indoles to form the squaraine dyes. The second chapter describes the synthesis of a new set of perimidine-based squaraine dyes. These new compounds are characterized using ¹H and ¹³C nuclear magnetic resonance (NMR). The optical and physicochemical properties are studied. Computational analyses were done to analyze the optical properties. Biological distribution studies and two modalities of imaging studies were conducted, fluorescence and optoacoustic. The optoacoustic analysis showed excellent properties that show potential uses as a contrast agent.