Polycyclic aromatic hydrocarbons (PAHs) have emerged as an intriguing class of organic compounds that are well suited for addressing longstanding challenges in materials chemistry. Specifically, the unique electronic properties of highly conjugated PAHs are postulated to promote close packing in the solid-state and enhance charge transport efficiency when used as semiconducting materials. However, current strategies for constructing these molecules are lengthy and do not allow for simple structural diversification. In this work we describe our alternative approach to synthesizing these molecules by coupling key fragments through a convergent strategy. We are able to obtain our bis(phenalenyl) targets in fewer steps than previous reports by harnessing new methods for achieving cyclization within polyarene frameworks. We anticipate that this new strategy will simplify access to these relatively unexplored and electronically unique PAHs, and enable more detailed investigation of their materials applications.

Synthetic strategy for rapid access to bis(phenalenyl)-based polycyclic aromatic hydrocarbons

254th National Meeting (2017)

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