In an attempt to produce a processible poly(pyrrol-2-ylsquaraine) by forming a copolymer of poly(pyrrodl-2-ylsquaraine) with polymethylmethacrylate, two synthetic routes were utilised. The first included forming the polysquaraine and then polymerising the attached methacrylate groups to form the desired product and the second proceeded via the preformed methacrylate polymer, containing N-alkylpyrrole side chains, which was then condensed with squaric acid. Difficulties arose in the first route when the polysquaraine product was found to be insoluble, hence preventing any further polymerisation but partial solubility during the second procedure did allow bissquaraines to be formed and, as a consequence, the resultant product exhibited fluorescent properties. Yet the desired processible poly(pyrrol-2-ylsquaraine) was not achieved.