Design, Synthesis, and Properties of Furan-Based Conjugated Materials

Five-membered heterocycles are one of the most prominent classes of aromatic building blocks for conjugated materials due to their excellent tunability. However, furan remains relatively underutilized due to its poor photostability, despite attractive features such as high solubility and planarity. This thesis will first present the development of ester functionalized polyfurans, which boast significantly improved stability over their alkyl functionalized analogues (Chapters 2 & 3). The unexpected helical structure of head-to-tail poly(3-hexylester furan) (HT-P3HEF) led to another significant theme; evaluating the impact of backbone composition, side chain identity, and regiochemistry on conformational tendencies for group 16 polymers. A combination of experiment and computation has deepened our understanding of these relationships (Chapters 2-4), and ultimately facilitated our group’s first report on conjugated macrocycles (Chapter 5). Current efforts focused on introducing precise sequence to these curved structures through rational design will also be discussed (Chapter 6), in addition to the overall outlook for this body of work and future directions (Chapter 7).