This thesis entitled ‘The Synthesis and Study of Novel Squaramide Scaffolds: From Sensors to Soft Materials’ is divided in 6 Chapters. Chapter 1, squaramide based receptors as potential anion sensors, gives a brief introduction into the history of anion recognition and the significant role anions play in biology and in the environment. A range of relevant examples of anion receptors and sensors from the literature are also given. This Chapter concludes with the aims of the research conducted in Chapter 2. In Chapter 2, a set of novel squaramide based anion receptors are described. The synthesis of each receptor is discussed in addition to their photophysical and anion binding properties. Chapter 3, squaramide based low molecular weight gelators (LMWGs), gives a concise background into the field of gels, from their formation and classification to their characteristics. It also gives a brief introduction on the topic of supramolecular gels with some relevant examples from the literature. This Chapter concludes with the aims of the research conducted in Chapter 4. In Chapter 4, a series of novel squaramides potential low molecular weight oragano-gelators (LMWOGs) are described. The synthesis of each new compound is discussed, in addition to preliminary gelation tests. In Chapter 5, an overall conclusion of the entire preceding chapter is given. Finally, in Chapter 6, general experimental procedures are outlined and the synthesis and characterisation of each of the compounds is given. Subsequently, literature references are provided and are followed by the Appendix which provides spectroscopic, titration data and photographic images to support work described in the main text.