Organic fluorophores are rarely synthesized at the undergraduate level, often because of the tedious procedures required for their synthesis. One example of such fluorophores, squaraines, are a class of near-infrared emitting fluorophores with unique photophysical properties. Squaraines are often synthesized via the condensation of an electron-rich aniline with squaric acid, refluxed overnight in a mixed solvent system. Reported herein are the syntheses of a variety of organic fluorophores in an undergraduate laboratory setting, including modifications to the literature-reported synthesis of a particular squaraine molecule that allowed it to be synthesized at the undergraduate level. The photophysical properties of these fluorophores can also be analyzed. Finally, the fluorophores can be used for a variety of interesting applications, including the fabrication of hybrid thin films and nanoparticles with fluorescent conjugated polymers.