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The ability to systematically alter the electronic properties of organic materials is vital for their incorporation into next-generation electronic devices. Polycyclic aromatic hydrocarbons (PAHs) are of significant interest for organic electronics, as relevant properties are highly dependent on their size, structure, and functionalities, and thus can be tuned to fit a wide variety of applications. Due to the enormous number of structural isomers available in larger PAHs, the development of design protocols is necessary to efficiently develop high-performing materials. Linear extension of the aromatic core, such as that seen in the acene series, is an efficient yet underexplored method for tuning the electronic properties of 2-D PAHs. The development of synthetic procedures is necessary to systematically explore the properties of the larger aromatic compounds. This work will explore novel synthetic routes that allow for the systematic exploration of acene-fused PAHs of similar size but vastly different electronic properties. Such work demonstrates that by strategically altering the mode of ring fusion, PAHs can be tuned for applications such as organic field-effect transistors (OFETs) and quantum information science (QIS). The impact of linear ring extension in 2-D PAHs is also explored, demonstrating that the electronic structure of larger PAHs can be systematically tuned with significant implications for their applications and stability. The functionalization of a series of organic dyes, with the goal of tuning their optical properties for implementation into wearable radiation sensors, will also be discussed.